Recent developments of ketene dithioacetal chemistry.

Ketene dithioacetals are versatile intermediates in organic synthesis. Extensive research, since the last decade, has given rise to new prospects in their chemistry. The objective of this review is twofold: first, to highlight the new prospects in the chemistry of functionalized ketene dithioacetals, and second, to provide an intrinsic link between ketene dithioacetal groups and a variety of other functional groups, which has brought out many new facts that will assist in future designs.

[1]  M. Muzard,et al.  Fluorinated ketene dithioacetals. 2. Synthesis of 2-hydroperfluoro acid derivatives from perfluoroketene dithioacetals , 1993 .

[2]  H. Hartzler 1,3-Dithiolium carbenes from acetylenes and carbon disulfide , 1973 .

[3]  Shengming Ma,et al.  Some typical advances in the synthetic applications of allenes. , 2005, Chemical reviews.

[4]  P. Langer,et al.  Diversity‐Oriented Synthesis of Chlorinated Arenes by One‐Pot Cyclizations of 4‐Chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes , 2009 .

[5]  Yunhui Li,et al.  A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones from α-oxoketene-S,S-acetals , 2011 .

[6]  Qun Liu,et al.  A Divergent Synthesis of Functionalized Unsaturated δ-Lactones from α-Alkenoyl-α-carboxyl Ketene Dithioacetals , 2007 .

[7]  V. Nenajdenko,et al.  Isocyanoacetate derivatives: synthesis, reactivity, and application. , 2010, Chemical reviews.

[8]  D. Procter,et al.  Beyond the Pummerer reaction: recent developments in thionium ion chemistry. , 2010, Angewandte Chemie.

[9]  K. Panda,et al.  Efficient Routes to Acenaphthylene‐Fused Polycyclic Arenes/Heteroarenes and Heterocyclic Fluoranthene Analogues , 2005 .

[10]  H. Ila,et al.  Benzoannelation of 2-methylindole via 1-N-carboxy-2-methylindole dianion: A direct regiospecific route to substituted and annelated carbazoles , 1998 .

[11]  Lei Zhao,et al.  Efficient Synthesis of Highly Functionalized Dihydropyrido[2,3-d]pyrimidines by a Double Annulation Strategy from α-Alkenoyl-α-carbamoyl Ketene-(S,S)-acetals , 2006 .

[12]  A. Mathews,et al.  Synthesis of pyrimidine-5-carbaldehydes from α-formylaroylketene dithioacetals , 2007 .

[13]  P. Kocieňski,et al.  Enantiospecific syntheses of pseudopterosin aglycones. Part 2. Synthesis of pseudopterosin K–L aglycone and pseudopterosin A–F aglycone via a B→BA→BAC annulation strategy , 2001 .

[14]  G. Nandi,et al.  One-pot two-component [3 + 2] cycloaddition/annulation protocol for the synthesis of highly functionalized thiophene derivatives. , 2011, The Journal of organic chemistry.

[15]  Qun Liu,et al.  One-pot synthesis of aza-morita-baylis-hillman adducts from α-oxo ketene-S,S-acetals, arylaldehydes and nitriles , 2005 .

[16]  J. Coustard 1,1-bis(Methylthio)-2-nitroethene in superacids: NMR study and reactivity of the formed hydroxynitrilium ion , 1995 .

[17]  F. Glorius,et al.  Towards mild metal-catalyzed C-H bond activation. , 2011, Chemical Society reviews.

[18]  Liming Zhang,et al.  Au-containing all-carbon 1,4-dipoles: generation and [4 + 2] annulation in the formation of carbo-/heterocycles. , 2008, Journal of the American Chemical Society.

[19]  H. Ila,et al.  2-phenyl-4-bis(methylthio)methyleneoxazol-5-one: versatile template for diversity oriented synthesis of heterocycles. , 2011, Organic & biomolecular chemistry.

[20]  F. Liang,et al.  Facile and Efficient Synthesis of Substituted 1,4‐Dithiafulvalenes from β‐Dicarbonyl Compounds , 2007 .

[21]  Qun Liu,et al.  A Clean, Facile and Practical Synthesis of α-Oxoketene S,S-Acetals in Water , 2006 .

[22]  Qun Liu,et al.  Vilsmeier-haack reaction of α-oxo ketene dithioacetals to α-chlorovinyl/ ethynyl ketene dithioacetals , 2004 .

[23]  Xiu-qing Song,et al.  Anodic oxidation of catechols in the presence of alpha-oxoketene N,N-acetals with a tetrahydropyrimidine ring: selective alpha-arylation reaction. , 2010, Organic & biomolecular chemistry.

[24]  X. Bi,et al.  Fe(III)-Catalyzed IntermolecularC(sp²)-C(sp³) DehydrationCoupling Reaction of Ketene Dithioacetals and PropargylAlcohols: Synthesis of Novel gem-Dialkylthiopenten-4-ynesand Further Conversion into Methyl Pent-4-ynoates , 2011 .

[25]  T. Ritter,et al.  Catalysis for fluorination and trifluoromethylation , 2011, Nature.

[26]  Qun Liu,et al.  Efficient synthesis of highly functionalized vinylogous thiol esters , 2010 .

[27]  V. Grushin,et al.  Aromatic trifluoromethylation with metal complexes. , 2011, Chemical reviews.

[28]  Daoben Zhu,et al.  Core-expanded naphthalene diimides fused with 2-(1,3-dithiol-2-ylidene)malonitrile groups for high-performance, ambient-stable, solution-processed n-channel organic thin film transistors. , 2010, Journal of the American Chemical Society.

[29]  Xueliang Huang,et al.  Sulfoxide-mediated α-arylation of carbonyl compounds. , 2011, Journal of the American Chemical Society.

[30]  F. Liang,et al.  Efficient one-pot synthesis of polyfunctionalized thiophenes via an amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles. , 2007, Organic letters.

[31]  Jun Liu,et al.  Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals. , 2010, Chemistry.

[32]  Hongjuan Yuan,et al.  Copper(II) Bromide/Boron Trifluoride Etherate-Cocatalyzed Cyclization of Ketene Dithioacetals and p-Quinones: a Mild and General Approach to Polyfunctionalized Benzofurans , 2010 .

[33]  J. Hwu,et al.  Mono-deoxygenation of Nitroalkanes, Nitrones, and Heterocyclic N-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent” , 1999 .

[34]  Alan R. Katritzky,et al.  [3+3] Benzannulations of benzenoid- and heteroaromatic-ring systems , 1999 .

[35]  H. Ila,et al.  1-Bis(methoxy)-4-bis(methylthio)-3-buten-2-one: useful three carbon synthon for synthesis of five and six membered heterocycles with masked (or unmasked) aldehyde functionality , 2003 .

[36]  S. Peruncheralathan,et al.  Regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles. , 2005, The Journal of organic chemistry.

[37]  S. Siaka,et al.  One-step synthesis of diazadihydroacenaphthylene derivatives with an isoxazoline ring, starting from 1-benzylamino-1-methylsulfanyl-2-nitroethenes , 2006 .

[38]  J. Hwu,et al.  Counterattack reagent: hexamethyldisilane in a direct synthesis of ketene dithioacetals and 2-trimethylsilyl-1,3-dithiane derivatives from 1,3-dithiane , 1992 .

[39]  Qun Liu,et al.  Efficient One-Pot Synthesisof 1,3-Disubstituted Pyridin-2(1H)-onesfrom α-Hydroxyketene S,S-Acetals under Vilsmeier Conditions , 2008 .

[40]  L. Pan,et al.  Dithiolane-Directed Tandem Oxidation/1,2-Benzyl Migration of Tetramic Acids under Ambient Conditions , 2012 .

[41]  L. Pan,et al.  Azo-coupling Decarboxylation Reaction of α-Carboxy Ketene Dithioacetals in Water–a New Route to 1,2-Diaza-1,3-butadienes , 2006 .

[42]  Qun Liu,et al.  Tandem [5+1] annulation-isocyanide cyclization: efficient synthesis of hydroindolones. , 2011, Chemical communications.

[43]  J. Fishpaugh,et al.  Synthesis of .alpha.-pyrones from vinylogous thiol esters and .alpha.-oxo ketene dithioacetals , 1988 .

[44]  R. K. Verma,et al.  InCl3 catalyzed domino route to 2H-chromene-2-ones via [4 + 2] annulation of 2-hydroxyarylaldehydes with α-oxoketene dithioacetal under solvent-free conditions , 2012 .

[45]  Q. Zhang,et al.  The first nonthiolic, odorless 1,3-propanedithiol equivalent and its application in thioacetalization. , 2003, The Journal of organic chemistry.

[46]  H. Rao,et al.  Nitroketene acetal chemistry. 3. Facile synthesis of nitroacetic acid triarylmethyl ortho esters from 1,1-di(methylsulfanyl)-2-nitroethylene. , 2005, The Journal of organic chemistry.

[47]  Ming Li,et al.  Solvent-free and efficient synthesis of imidazo[1,2-a]pyridine derivatives via a one-pot three-component reaction , 2012 .

[48]  Ming Li,et al.  Chemistry of heterocyclic ketene aminals: construction of imidazo(pyrido)[1,2-a]pyridines and imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-catalyzed tandem annulations. , 2011, The Journal of organic chemistry.

[49]  Wen Tian,et al.  The sterochemistry and absolute configurations of the metal complexes of novel optically active NSSN system tetradentate ligands. Cobalt(III) complexes of S,S′-bis(β-aminoethyl)-trans-1,2-dithiocyclohexane. Crystal and molecular structure of s-cis[Co(adch)Cl2]Cl·C2H5OH , 1997 .

[50]  Y. Ammar,et al.  Some reactions with ketene dithioacetals part I: synthesis of antimicrobial pyrazol. , 2001, Farmaco.

[51]  G. Nandi,et al.  Highly convergent one-pot four-component regioselective synthesis of 4H-benzo[f]chromenes via annulation of β-oxodithioesters , 2012 .

[52]  G. Elgemeie,et al.  Novel Synthesis of Thioguanine and Sulfanylpurine Analogues: Reaction of Heterocyclic Ketene Dithioacetals with Nucleophiles , 1998 .

[53]  Daoben Zhu,et al.  One-pot synthesis of core-expanded naphthalene diimides: enabling N-substituent modulation for diverse n-type organic materials. , 2012, Organic letters.

[54]  P. Kocieňski,et al.  A synthetic approach to the pseudopterosins , 1996 .

[55]  M. Shi,et al.  The synthesis of chromenes, chromanes, coumarins and related heterocycles via tandem reactions of salicylic aldehydes or salicylic imines with α,β-unsaturated compounds , 2007 .

[56]  T. Okauchi,et al.  Synthesis and Synthetic Application of Phosphonoketene Dithioacetals. New Synthesis of Dithioallenes and (alpha-Dithiocarboxyvinyl)phosphonates. , 1996, The Journal of organic chemistry.

[57]  A. Göller,et al.  Efficient regioselective synthesis of 6-amino-5-benzoyl-1-substituted 2(1H)-pyridinones. , 2005, The Journal of organic chemistry.

[58]  S. Sundar,et al.  Molecular Docking and in Vitro Antileishmanial Evaluation of Chromene-2-thione Analogues. , 2012, ACS medicinal chemistry letters.

[59]  F. Liang,et al.  Intramolecular thia-anti-Michael addition of a sulfur anion to enones: a regiospecific approach to multisubstituted thiophene derivatives. , 2006, The Journal of organic chemistry.

[60]  R. K. Verma,et al.  4-Dimethylamino pyridine-promoted one-pot three-component regioselective synthesis of highly functionalized 4H-thiopyrans via heteroannulation of β-oxodithioesters. , 2012, ACS combinatorial science.

[61]  S. Peruncheralathan,et al.  Domino carbocationic rearrangements of α-[bis(methylthio)methylene]alkyl-2-(heteroaryl)cyclopropyl ketones , 2004 .

[62]  A. Padwa,et al.  The Pummerer reaction: methodology and strategy for the synthesis of heterocyclic compounds. , 2004, Chemical reviews.

[63]  A. Padwa,et al.  Linked Pummerer-Mannich Ion Cyclizations for Heterocyclic Chemistry , 2002 .

[64]  S Kumar,et al.  Nitroketene dithioacetal chemistry. Part 2: Synthesis of novel 4-(alkylsulfanyl)-2-[1-nitromethylidene]-1,3-dithioles from the dipotassium salt of 2-nitro-1,1-ethylenedithiol , 2003 .

[65]  W. O. Moss,et al.  2-Amino ketene S,S-acetals as α-amino acid homoenolate equivalents. Synthesis of 3-substituted prolines and molecular structure of 2-(N-pivaloylpyrrolidin-2-ylidene)-1,3-dithiane , 1992 .

[66]  S. Nair,et al.  A FACILE SYNTHESIS OF β-OXOTHIOLCARBOXYLATES FROM α-OXOKETENEDITHIOACETALS* , 2001 .

[67]  C. V. Asokan,et al.  Vilsmeier–Haack reactions of α-hydroxyketenedithioacetals: a facile synthesis of substituted pyridines , 2002 .

[68]  Jinglan Zhou,et al.  Ketene dithioacetals in the aza-Diels-Alder reaction with N-arylimines: a versatile approach to tetrahydroquinolines, 2,3-dihydro-4-quinolones, and 4-quinolones. , 2002, Organic letters.

[69]  G. Elgemeie,et al.  Synthesis of some novel α-cyanoketene S,S-acetals and their use in heterocyclic synthesis , 1997 .

[70]  Qun Liu,et al.  The Alkoxy Substitution Reaction on α-Oxo Ketene Dithioacetals: A New Access to α-Oxo Ketene O,S-/O,O-Acetals , 2004 .

[71]  F. Liang,et al.  Copper-mediated C-N bond formation via direct aminolysis of dithioacetals. , 2006, Organic letters.

[72]  C. Brulé,et al.  Fluoride-induced coupling of perfluoroketene dithioacetals with silyl alkynes: A way towards new polyfunctionalized trifluoromethyl building blocks , 2007 .

[73]  A. Alizadeh,et al.  Novel heterocyclic β-nitroenamines-based on a one-pot three-component reaction: a facile synthesis of fully substituted 1H-pyrrolo[1,2-a]-fused-1,3-diazaheterocycles , 2010 .

[74]  D. Basavaiah,et al.  The Baylis-Hillman reaction: a novel concept for creativity in chemistry. , 2012, Chemical Society reviews.

[75]  P. Knochel,et al.  Cesium hydroxide catalyzed addition of alcohols and amine derivatives to alkynes and styrene , 1999 .

[76]  M. Muzard,et al.  A Straightforward and General Strategy Towards 1,5‐Dithio‐1‐enopyranosides , 2008 .

[77]  Qun Liu,et al.  Bicyclization of Isocyanides: A Synthetic Strategy for Fused Pyrroles , 2011 .

[78]  G. Petrillo,et al.  Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene , 2002 .

[79]  J. Podlech,et al.  Enolate addition to a 2-alkylidene[1,3]dithiane-derived bissulfoxide. A new a(2)-acceptor. , 2005, Organic letters.

[80]  S. Rozen Selective Reactions of Bromine Trifluoride in Organic Chemistry , 2010 .

[81]  R. Dieter Synthesis of a-pyrones from a-oxo ketene dithioacetals , 1986 .

[82]  Qun Liu,et al.  Ethynyl ketene-S,S-acetals: the highly reactive electron-rich dienophiles and applications in the synthesis of 4-functionalized quinolines via a one-pot three-component reaction. , 2007, The Journal of organic chemistry.

[83]  Xiaolan Fu,et al.  A Facile and Divergent Synthesis of Substituted Pyridine-2,4(1H,3H)-diones and 4H-Thiopyran-4-ones from α-Alkenoyl-α-carbamoyl Ketene-S,S-acetals , 2010 .

[84]  P. Schreiner,et al.  [1,3]Dithian-2-ylidene. , 2006, Angewandte Chemie.

[85]  O. Barun,et al.  Studies on regioselective addition of benzylic organometallics to α-oxoketene dithioacetals in our aromatic annelation protocol , 2001 .

[86]  Recent Progress in the Use of Vilsmeier-Type Reagents , 2010 .

[87]  J. Mokhtari,et al.  Synthesis of the novel pyrimido[1,6-a]pyrimidine and imidazo[1,2-c]pyrimidine derivatives based on heterocyclic ketene aminals , 2012 .

[88]  J. Wolfe,et al.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction. , 2005, Journal of the American Chemical Society.

[89]  M. Hojo,et al.  Studies of organosilicon chemistry. 107. N-(silylmethyl)-substituted ketene N,S-acetals as a synthetic equivalent of a novel 1,3-dipolar reagent, alkylideneazomethine ylides: synthesis and [3 + 2] cycloadditions , 1990 .

[90]  Hai‐Chao Xu,et al.  Intramolecular anodic olefin coupling reactions: use of the reaction rate to control substrate/product selectivity. , 2010, Angewandte Chemie.

[91]  R. K. Verma,et al.  An expedient route to highly functionalized 2H-chromene-2-thiones via ring annulation of β-oxodithioesters catalyzed by InCl3 under solvent-free conditions , 2011 .

[92]  Mei-Xin Zhao,et al.  A novel one-pot reaction of heterocyclic ketene aminals: Synthesis of a small library of tetrahydropyridinone-fused 1,3-diazaheterocycles , 2006 .

[93]  T. Okuyama Acid-catalyzed hydrolysis of 2-methylene-1,3-dithiolane. Complete analysis of a three-stage reaction mechanism , 1984 .

[94]  Zhan-Jiang Li,et al.  THE SYNTHESIS OF FLUOROHETEROCYCLIC KETENE AMINALS , 2001 .

[95]  Meining Wang,et al.  Novel and convenient synthesis of polyfunctionalized quinolines, quinolones and their annulation reactions , 2001 .

[96]  Qun Liu,et al.  Sulfuric Acid‐Catalyzed Regioselective Alkylation of Indoles and β‐Naphthols with Ketene Dithioacetal‐Based Allylic Alcohols , 2011 .

[97]  F. Couty,et al.  Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes. , 2009, Organic letters.

[98]  A. Goel,et al.  Natural and synthetic 2H-pyran-2-ones and their versatility in organic synthesis☆ , 2009 .

[99]  A. Alizadeh,et al.  A Novel and One-Pot MulticomponentApproach to the Synthesis of Dihyroindeno[1,2-b]pyrroles and Indeno[2′,1′:4,5]pyrrolo[1,2-a]-Fused 1,3-Diazaheterocycles , 2011 .

[100]  H. Yorimitsu,et al.  2-(2,2,2-Trifluoroethylidene)-1,3-dithiane monoxide as a trifluoromethylketene equivalent. , 2009, Organic letters.

[101]  Qun Liu,et al.  Aerobic, Cu-catalyzed desulfitative C-C bond-forming reaction of ketene dithioacetals/vinylogous thioesters and arylboronic acids. , 2011, Chemical communications.

[102]  B. Myrboh,et al.  Synthetic studies on KF-alumina-catalysed reaction of substituted and unsubstituted aryl-oxoketene dithioacetals and 1H-pyrazone-5(4H)-one: a convenient synthesis of pyrazolo[3,4-b]pyridine and pyrazolo[1,5-a]pyrimidine , 2009 .

[103]  H. Rao,et al.  Nitroketene acetal chemistry: efficient synthesis of 2-amino-3-nitro-4H-chromenes , 2009 .

[104]  A. Yadav,et al.  A Novel Radical Cyclization Approach to Thieno‐Fused Heterocycles , 2011 .

[105]  M. Kolb Ketene dithioacetals in organic synthesis : recent developments , 1990 .

[106]  P. Frère,et al.  Synthesis of 3,4-alkoxythieno[2,3-b]thiophene derivatives. The first block copolymer associating the 3,4-ethylenedioxythieno[2,3-b]thiophene (EDOThT) unit with 3,4-ethylenedioxythiophene (EDOT) moieties. , 2007, Organic & biomolecular chemistry.

[107]  Qun Liu,et al.  Tandem double-Michael-addition/cyclization/acyl migration of 1,4-dien-3-ones and ethyl isocyanoacetate: stereoselective synthesis of pyrrolizidines. , 2009, Angewandte Chemie.

[108]  G. Nandi,et al.  Highly Regioselective One-Pot, Three-Component Synthesis of 1-Aryl-3,4-Substituted/Annulated-5-(Cycloamino)/(Alkylamino)pyrazoles from β-Oxodithioesters , 2012 .

[109]  J. Herrmann,et al.  Ketene thioacetal monoxides: A novel and versatile class of two-carbon michael receptors , 1973 .

[110]  A. Yadav,et al.  Domino carbocationic rearrangement of alpha-[bis(methylthio)methylene]alkyl-2-(3/2-indolyl) cyclopropyl ketones. , 2007, The Journal of organic chemistry.

[111]  Jingping Zhang,et al.  Polarity-reversible conjugate addition tuned by remote electronic effects. , 2010, Organic letters.

[112]  A. Cousson,et al.  Synthesis of 6- to 10-membered ring (E)-hydroxyiminohydroazaazoniabenzocycloalkenes derivative from cyclization of 2-nitromethylene-1-(ω-phenylalkyl)imidazolidine or 2-nitromethylene-1-(ω-phenylalkyl)hexahydropyrimidine in trifluoromethanesulfonic acid , 2006 .

[113]  D. Basavaiah,et al.  Recent contributions from the Baylis-Hillman reaction to organic chemistry. , 2010, Chemical reviews.

[114]  H. Ila,et al.  α-Oxoketene-S,S-, N,S- and N,N-acetals: Versatile intermediates in organic synthesis , 1990 .

[115]  T. Kataoka,et al.  The chalcogeno-Baylis–Hillman reaction of ketones and α-dicarbonyl compounds , 2002 .

[116]  O. Singh,et al.  Application of beta-oxodithioesters in domino and multicomponent reactions: facile route to dihydropyrimidines and coumarins. , 2009, The Journal of organic chemistry.

[117]  R. K. Verma,et al.  Heteroaromatic Annulation Studies on 2-[Bis(methylthio)methylene]-1,3-indanedione: Efficient Routes to Indenofused Heterocycles. , 2010 .

[118]  J. Vicente,et al.  CS2 insertion into a gold–carbon bond. First syntheses and characterization of 2,2-diacetylethylene-1,1-dithiolato complexes. Crystal structure of [N(PPh3)2][Au{η2-S2CC(COMe)2}2]† , 1997 .

[119]  T. Okauchi,et al.  Lewis acid-promoted deoxygenative di[beta,beta-bis(ethylthio)]vinylation of aldehydes with trimethylsilylketene bis(ethylthio)acetal. , 2001, The Journal of organic chemistry.

[120]  A. Alizadeh,et al.  Efficient One-Pot Synthesisof Spirooxindole Derivatives Containing 1,4-Dihydropyridine-Fused-1,3-DiazaheterocycleFragments via Four-Component Reaction , 2010 .

[121]  A. de Meijere,et al.  Isocyanides in the synthesis of nitrogen heterocycles. , 2010, Angewandte Chemie.

[122]  Jingping Zhang,et al.  Intramolecular Aza-Anti-Michael Addition of an Amide Anion to Enones: A Regiospecific Approach to Tetramic Acid Derivatives , 2007 .

[123]  V. Timoshenko,et al.  Domino nucleophilic trifluoromethylations of alkyl perfluorodithioesters , 2009 .

[124]  Qun Liu,et al.  Alpha-alkenoyl ketene S,S-acetal-based multicomponent reaction: an efficient approach for the selective construction of polyfunctionalized cyclohexanones. , 2009, The Journal of organic chemistry.

[125]  Haifeng Yu,et al.  Direct alkenylation of indoles with alpha-oxo ketene dithioacetals: efficient synthesis of indole alkaloids meridianin derivatives. , 2009, Angewandte Chemie.

[126]  F. Liang,et al.  Domino Reaction of Acyclic α,α‐Dialkenoylketene S,S‐Acetals and Diamines: Efficient Synthesis of Tetracyclic Thieno[2,3‐b]thiopyran‐Fused Imidazo[1,2‐a]pyridine/Pyrido[1,2‐a]pyrimidines , 2006 .

[127]  A. Alizadeh,et al.  A Unique Approach to Catalyst-Free,One-Pot Synthesis of Spirooxindole-Pyrazolines , 2012 .

[128]  O. Jung,et al.  Subtle Ring Size Effects on Bonding Mode. Structures and Properties of Platinum(II) Complexes Involving Sulfur-Containing Dicarboxylate Ligands S-(CH(2))(n)-S-C=C(COO(-))(2) (n = 2, 3, 4). , 1996, Inorganic chemistry.

[129]  E. R. Anabha,et al.  Simple methods to synthesize 2-pyridones: reactions of 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and cyanoacetamide , 2008 .

[130]  Elisabetta Brenna,et al.  Recent advances in the benzannulation of substituted 3-alkoxycarbonyl-3,5-hexadienoic acids and 3-alkoxycarbonylhex-3-en-5-ynoic acids to polysubstituted aromatics. , 2007, Chemistry.

[131]  Chenglin Sun,et al.  Palladium-catalyzed cross-coupling of internal alkenes with terminal alkenes to functionalized 1,3-butadienes using C-H bond activation: efficient synthesis of bicyclic pyridones. , 2010, Angewandte Chemie.

[132]  Qun Liu,et al.  A C-C bond formation reaction at the α-carbon atom of α-oxo ketene dithioacetals via the Baylis-Hillman type reaction , 2005 .

[133]  Enrico Perspicace,et al.  One-pot synthesis of new tetrasubstituted thiophenes and selenophenes , 2009 .

[134]  Ming Li,et al.  Reaction of ketene dithioacetals with pyrazolylcarbohydrazide: Synthesis and biological activities of ethyl 5‐amino‐1–(5′‐methyl‐1′‐t‐butyl‐4′‐pyrazolyl)carbonyl‐3‐methylthio‐1 H‐pyrazole‐4‐carboxylate , 2010 .

[135]  V. Bajpai,et al.  Thermally stable nonaggregating pyrenylarenes for blue organic light-emitting devices. , 2011, The Journal of organic chemistry.

[136]  Gloria Hernández-Torres,et al.  Enantiopure sulfoxides: recent applications in asymmetric synthesis. , 2009, Chemical communications.

[137]  Yulan Chen,et al.  Three-component solvent-free synthesis of highly substituted bicyclic pyridines containing a ring-junction nitrogen , 2010 .

[138]  T. Minami,et al.  Reaction of 2,2-difluorovinyl ketones with heteroatom nucleophiles: A general one-pot synthesis of α-oxoketene acetals , 1994 .

[139]  Jie Huang,et al.  Efficient one-pot synthesis of highly substituted thiophene library from 1,3-dicarbonyl compounds. , 2008, Journal of combinatorial chemistry.

[140]  Qun Liu,et al.  TiCl4 mediated Michael addition reactions of α-cyanoketene-S,S-acetals with enones , 2006 .

[141]  P. K. Bharadwaj,et al.  Lewis acid-induced rearrangment of α-[bis(methylthio)methylene]ethyl-2-styrylcyclopropylcarbinols: unexpected formation of a novel bicyclo[3.2.1]octadiene framework , 2000 .

[142]  V. Kumar,et al.  Synthesis, electrochemical and optical properties of stable yellow fluorescent fluoranthenes. , 2010, Journal of Organic Chemistry.

[143]  Qun Liu,et al.  Synthesis of functionalized allylic sulfoxides and their use in the construction of 2,3,4-trisubstituted furans via a [3 + 2] annulation. , 2008, The Journal of organic chemistry.

[144]  T. Fukuyama,et al.  Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO. , 2010, Chemical communications.

[145]  F. Liang,et al.  A tandem reaction of 2-acetylmethylene-1,3-dithiolanes via fragmentation of the dithiolane ring in the presence of amines: a facile route to functionalized thioamides , 2007 .

[146]  Qun Liu,et al.  Proton‐Promoted Hydroamination of 3‐Dialkylthiomethylene‐1,4‐pentadiynes with o‐Phenylenediamines: A Facile Route to Benzo[b][1,4]diazepines , 2008 .

[147]  R. K. Verma,et al.  InCl3-driven regioselective synthesis of functionalized/annulated quinolines: scope and limitations. , 2012, Chemistry, an Asian journal.

[148]  L. Pan,et al.  Tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition: highly diastereoselective one pot synthesis of fused oxazolines. , 2010, Chemical communications.

[149]  A. Hagooly,et al.  Alpha-trifluoromethylation of secondary and sterically hindered carboxylates with use of BrF3. , 2004, The Journal of organic chemistry.

[150]  Haifeng Yu,et al.  Regioselective synthesis of multisubstituted pyrazoles via cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines , 2011 .

[151]  Yu Hisadome,et al.  One-pot synthesis of polysubstituted pyridine derivatives using ketene dithioacetals , 2007 .

[152]  Jiping Chen,et al.  Regio- and stereoselective synthesis of multisubstituted olefins and conjugate dienes by using α-oxo ketene dithioacetals as the building blocks. , 2011, Organic letters.

[153]  Qun Liu,et al.  A synthetic strategy for polyfunctionalized bicyclo[3.3.1]nonanes based on a tandem three-component [3 + 2] cycloaddition of alpha-cinnamoyl ketene-S,S-acetals with oxalyl chloride. , 2009, The Journal of organic chemistry.

[154]  Jun Lin,et al.  Cascade reaction of isatins with heterocyclic ketene aminals: synthesis of imidazopyrroloquinoline derivatives. , 2011, Organic letters.

[155]  W. Schroth,et al.  6-Alkylthio-1,3-thiazinium-salze aus Acylketen-S,S-acetalen und Thioamiden , 1982 .

[156]  H. Ila,et al.  Trimethylsilyl chloride assisted conjugate addition-elimination of organocopper reagents to 2-bis(methylthio)nitroethylene: An efficient and highly stereoselective synthesis of 2-methylthio-2-alkyl/aryl-1-nitroethylenes and their application for synthesis of nitroheterocycles , 1998 .

[157]  J. D. Brandt,et al.  Anodic cyclization reactions and the synthesis of (−)-crobarbatic acid , 2008 .

[158]  A. Hagooly,et al.  General Method for the Preparation of β,β-Difluoroacrylates Using BrF3 , 2004 .

[159]  H. Ila,et al.  Heteroaromatic annulation studies on 10,11-dihydro-11-[bis(methylthio)methylene]dibenzoxepin-10-one: a facile access to novel dibenzoxepino[4,5]-fused heterocycles , 2007 .

[160]  Dawei Zhang,et al.  Double isocyanide cyclization: a synthetic strategy for two-carbon-tethered pyrrole/oxazole pairs. , 2011, Journal of the American Chemical Society.

[161]  R. Eisenberg,et al.  Catalytic Nazarov Cyclization: The State of the Art , 2011 .

[162]  J. Šrogl,et al.  Thiol Ester−Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone Synthesis , 2000 .

[163]  Xueliang Huang,et al.  Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements , 2012 .

[164]  Weiping Tang,et al.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition. , 2011, Angewandte Chemie.

[165]  Qun Liu,et al.  Iododecarboxylation Reactions of α‐Oxo Ketene Dithioacetals: The New Route to α‐Iodo Ketene Dithioacetals , 2004 .

[166]  Y. Sohn,et al.  LINKAGE ISOMERISM OF (DIAMINE)PLATINUM(II) COMPLEXES OF SULFUR-CONTAINING YLIDENEMALONATE LIGANDS , 1997 .

[167]  N. Misra,et al.  An efficient highly regioselective synthesis of 2,3,4-trisubstituted pyrroles by cycloaddition of polarized ketene S,S- and N,S-acetals with activated methylene isocyanides. , 2007, The Journal of organic chemistry.

[168]  T. Okauchi,et al.  Synthesis and Synthetic Utilization of alpha-Functionalized Vinylphosphonates Bearing beta-Oxy or beta-Thio Substituents. , 1998, The Journal of organic chemistry.

[169]  Qun Liu,et al.  A new route to extended tetrathiafulvalenes from α-acetyl ketene- S , S -acetals , 2006 .

[170]  Jingping Zhang,et al.  Heteroatom-substituted expanded radialenes: one-pot synthesis and characterization of expanded 1,3-dithiolane[n]radialenes. , 2005, The Journal of organic chemistry.

[171]  Jimmy Wu,et al.  Phosphorothioic acids and related compounds as surrogates for H2S--synthesis of chiral tetrahydrothiophenes. , 2012, Journal of the American Chemical Society.

[172]  J. Coustard Synthesis of Six- to Nine-Membered Ring Oximinoorthodithiolactones by Cyclization of Nitroketene S,S-Acetals in Trifluoromethanesulfonic Acid , 2001 .

[173]  Qun Liu,et al.  Highly efficient synthesis of 3-amino-/alkylthio-cyclobut-2-en-1-ones based on the cyclization of acyl ketene dithioacetals. , 2010, Chemical communications.

[174]  Jie Huang,et al.  Efficient synthesis of α-alkylidene-β-lactams via NaOH-promoted intramolecular aza-Michael addition of α-carbamoyl ketene-S,S-acetals in aqueous media , 2008 .

[175]  Qun Liu,et al.  Domino Reaction of α-Acetyl-α-carbamoyl Ketene Dithioacetals with Vilsmeier Reagents: A Novel and Efficient Synthesis of 4-Halogenated 2(1H)-Pyridinones , 2007 .

[176]  H. Yorimitsu,et al.  Synthesis of 3-trifluoromethylbenzo[b]furans from phenols via direct ortho functionalization by extended Pummerer reaction. , 2010, Journal of the American Chemical Society.

[177]  H. Rao,et al.  Nitroketene dithioacetal chemistry: Synthesis of 2-alkylthio-3-nitrothiophenes from nitroketene dithioacetate and chloromethyl ketones. , 2009, The Journal of organic chemistry.

[178]  R. Madsen,et al.  Modern methods for shortening and extending the carbon chain in carbohydrates at the anomeric center , 2011 .

[179]  A. Yadav,et al.  Synthesis of Novel Substituted Phenanthrenes and Polycyclic Heteroarenes by Pd-Catalyzed, Direct, Intramolecular Arylation/Heteroarylation , 2010 .

[180]  R. Dieter α-Oxo ketene dithioacetals and related compounds: versatile three-carbon synthons , 1986 .

[181]  A. Padwa,et al.  A new method for the preparation of 2-thio substituted furans by methylsulfanylation of gamma-dithiane carbonyl compounds. , 2002, The Journal of organic chemistry.

[182]  L. Pan,et al.  Direct Synthesis of 6-Azabicyclo[3.2.1]oct-6-en-2-ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects , 2011 .

[183]  Bing Li,et al.  [5 + 1] annulation: a synthetic strategy for highly substituted phenols and cyclohexenones. , 2005, Journal of the American Chemical Society.

[184]  Qun Liu,et al.  IODODECARBOXYLATION OF α-CARBOXYLATE, α-CINNAMOYL KETENE CYCLIC DITHIOACETALS , 2002 .

[185]  S. Zard,et al.  An unexpected synthesis of ketene monothioacetals. , 2006, Chemical communications.

[186]  K. Panda,et al.  Heteroaromatic annulation of 2-methyl/2-cyanomethylbenzimidazole dianions with alpha-oxoketene dithioacetals: a highly regioselective synthetic protocol for 1,2- and 2,3-substituted/annulated pyrido[1,2-a]benzimidazoles. , 2003, The Journal of organic chemistry.

[187]  G. Olah,et al.  N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics. , 2004, Journal of the American Chemical Society.

[188]  Ming Li,et al.  Modulating the reactivity of heterocyclic ketene aminals in MCR: selective construction of tetrahydrobenzo[b]imidazo[3,2,1-ij][1,8]naphthyridines. , 2010, The Journal of organic chemistry.

[189]  B. Trost,et al.  Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D. , 2012, Journal of the American Chemical Society.

[190]  Anamik Shah,et al.  A concise synthetic strategy to functionalized chromenones via [5+1] heteroannulation and facile C-N/C-S/C-O bond formation with various nucleophiles , 2011 .

[191]  Jie Huang,et al.  [4+2] Annulation – Convenient Synthesis of Substituted Dihydropyranones in Aqueous Media , 2009 .

[192]  David R Spring,et al.  Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules. , 2010, Nature communications.

[193]  Hai‐Chao Xu,et al.  Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines. , 2010, Journal of the American Chemical Society.

[194]  A. Hagooly,et al.  The First General Method for α-Trifluoromethylation of Carboxylic Acids Using BrF3. , 2004 .

[195]  L. Bhat,et al.  Rearrangement studies on acylketene O-prop-2-ynyl S-methylmonothioketals , 1994 .

[196]  Hongjuan Yuan,et al.  Tandem Nazarov cyclization-halovinylation of divinyl ketones under Vilsmeier conditions: synthesis of highly substituted cyclopentadienes. , 2010, Chemical communications.

[197]  H. Ila,et al.  Reaction of alpha-oxoketene-N,S-arylaminoacetals with Vilsmeier reagents: an efficient route to highly functionalized quinolines and their benzo/hetero-fused analogues. , 2003, The Journal of organic chemistry.

[198]  S. Takada,et al.  S-silylmethyl-substituted ketene dithioacetals as synthetic equivalent of a novel 1,3-dipolar reagent, alkylidenethiocarbonyl ylide; synthesis and [3+2] cycloaddition reactions , 1994 .

[199]  Y. Tominaga,et al.  Synthesis and reaction of 6‐substituted 3‐methoxycarbonyl‐4‐methylthio‐2H‐pyran‐2‐one derivatives , 1987 .

[200]  Hongjuan Yuan,et al.  Copper(II)‐Catalyzed CC Bond‐Forming Reactions of α‐Electron‐Withdrawing Group‐Substituted Ketene S,S‐Acetals with Carbonyl Compounds and a Facile Synthesis of Coumarins , 2009 .

[201]  B. Alcaide,et al.  Exploiting [2+2] cycloaddition chemistry: achievements with allenes. , 2010, Chemical Society reviews.

[202]  E. Lewandowska Substitution at the α-carbons of α,β-unsaturated carbonyl compounds: anti-Michael addition , 2007 .

[203]  J. Köditz,et al.  Synthesis and reactions of pyridinethiones , 1993 .

[204]  Chengchu Zeng,et al.  One-pot electrochemical synthesis of fused indole derivatives containing active hydroxyl groups in aqueous medium. , 2009, The Journal of organic chemistry.

[205]  M. Iyoda,et al.  Conjugated macrocycles: concepts and applications. , 2011, Angewandte Chemie.

[206]  A. Yadav,et al.  Novel Route to 2,3-Substituted Benzo[b]thiophenes via Intramolecular Radical Cyclization. , 2009, The Journal of organic chemistry.

[207]  H. Rao,et al.  Condensation of alpha-aroylketene dithioacetals and 2-hydroxyarylaldehydes results in facile synthesis of a combinatorial library of 3-aroylcoumarins. , 2006, The Journal of organic chemistry.

[208]  Jie Huang,et al.  A facile and convenient one-pot synthesis of polysubstituted thiophenes from 1,3-dicarbonyl compounds in water , 2007 .

[209]  V. Timoshenko,et al.  Thiophilic nucleophilic trifluoromethylation of α-substituted dithioesters. Access to S-trifluoromethyl ketene dithioacetals and their reactivity with electrophilic species , 2012 .

[210]  Zhihui Zhang,et al.  Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins. , 2011, Journal of the American Chemical Society.

[211]  R. Sreekumar,et al.  Diastereoselective Asymmetric Induction in the Thio-Claisen Rearrangement Over Zeolites , 1997 .

[212]  A. Alizadeh,et al.  Practical and Novel One-Pot Protocol for the Synthesis of Highly Functionalized Pyridinols and Pyrido[1,2-a]-Fused 1,3-Diazaheterocycles , 2011 .

[213]  G. Calestani,et al.  Diazo transfer reaction of 2-(trimethylsilyl)-1,3-dithiane with tosyl azide. Reactivity of transient 2-diazo-1,3-dithiane , 1995 .

[214]  Sushobhan Chowdhury,et al.  Regioselective synthesis of tetrahydrothiochromen-5-ones via a one-pot three-component solvent-free domino protocol. , 2011, Organic letters.

[215]  P. Cozzi,et al.  Direct Nucleophilic SN1‐Type Reactions of Alcohols , 2011 .

[216]  H. Ila,et al.  A new general regiocontrolled synthesis of highly substituted and condensed indoles via heteroaromatic annelation , 1997 .

[217]  E. R. Anabha,et al.  Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals , 2011 .

[218]  E. Anders,et al.  1,3‐Thiazoline‐5‐thiolates and 1,3‐Thiazole‐5(2H)‐thiones by [3+2]‐Cycloaddition of Carbon Disulfide to Metalated 4‐Alkylidene‐4H‐pyridin‐1‐ides , 2005 .

[219]  Qun Liu,et al.  One‐Pot Synthesis of Polyfunctionalized 4H‐Chromenes and Dihydrocoumarins Based on Copper(II) Bromide‐Catalyzed CC Coupling of Benzylic Alcohols with Ketene Dithioacetals , 2010 .

[220]  Wei Wang,et al.  Chemistry and biology of multicomponent reactions. , 2012, Chemical reviews.

[221]  Qun Liu,et al.  A novel and facile synthesis of dienals and substituted 2H-pyrans via the Vilsmeier reaction of α-oxo-ketenedithioacetals , 2004 .

[222]  Q. Zhang,et al.  BF3.Et2O-catalyzed direct carbon-carbon bond formation of alpha-EWG Ketene-(S,S)-acetals and alcohols and synthesis of unsymmetrical biaryls. , 2007, The Journal of organic chemistry.

[223]  Qun Liu,et al.  Highly efficient C-C bond-forming reactions of an α-cyanoketene dithioacetal with aldehydes and ketones , 2006 .

[224]  W. O. Moss,et al.  Ketene dithioacetals as 1,3-dipolarophiles. Applications to the synthesis of cyclic amino acids , 1990 .

[225]  A. Kutateladze,et al.  Interrupted oligomerization revisited: simple and efficient one-pot multicomponent approach to versatile synthetic intermediates. , 2007, Organic letters.

[226]  B. Zwanenburg,et al.  Sulfoxide induced sigmatropic rearrangement (SISR) of methyl 1-methylsulfanylvinyl sulfoxides , 1997 .

[227]  I. Löfberg,et al.  2-(2,2,2-Trifluoroethylidene)-1,3-dithianes. New Intermediates for the Preparation of CF3-Containing Compounds. , 1989 .

[228]  Qun Liu,et al.  Synthesis of 2‐Benzylthio‐5‐phenyl‐3,4‐disubstituted Thiophenes by Intramolecular Condensation of α‐Oxo Ketene Dibenzyl‐thioacetals , 2010 .

[229]  B. Feringa,et al.  Recent advances in enantioselective copper-catalyzed 1,4-addition. , 2009, Chemical Society reviews.

[230]  B. Liu,et al.  Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid. , 2002, Journal of the American Chemical Society.

[231]  Reichel Samuel,et al.  Dimsyl Anion Induced Demethylation and Fragmentation Reactions of α-Oxoketenedithioacetals , 2001 .

[232]  O. Singh,et al.  Cupric chloride promoted regioselective C-allylation of enaminones , 2008 .