Regioselective 5-exo-dig oxy-cyclization of 2-alkynylbenzamide for the synthesis of isobenzofuran-1-imines and isobenzofuran.

A TBAB-mediated brominative 5-exo-dig oxy-cyclization of 2-alkynylbenzamide is described here for the synthesis of isobenzofuran-1-imines and isobenzofuran derivatives at room temperature with a high efficiency and a broad reaction scope. The resulting isobenzofuran derivatives are also applied for synthesising various substituted isobenzofuran derivatives.

[1]  Hongwei Zhou,et al.  Regioselective Neighboring-Group-Participated 2,4-Dibromohydration of Conjugated Enynes: Synthesis of 2-(2,4-Dibromobut-2-enoyl)benzoate and Its Applications. , 2018, Organic letters.

[2]  Jinlai Li,et al.  Visible-light-mediated radical cascade reaction: synthesis of 3-bromocoumarins from alkynoates. , 2017, Organic & biomolecular chemistry.

[3]  Gangguo Zhu,et al.  Copper-Catalyzed Radical Cascade Difluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes: A Route to Difluoromethylated Naphthoquinones. , 2017, The Journal of organic chemistry.

[4]  Hongwei Zhou,et al.  Synthesis of benzil-o-carboxylate derivatives and isocoumarins through neighboring ester-participating bromocyclizations of o-alkynylbenzoates. , 2017, Organic & biomolecular chemistry.

[5]  Hongwei Zhou,et al.  KBr/K2S2O8-mediated dibromohydration of N-(2-alkynylaryl)acetamide , 2017 .

[6]  Xuefeng Jiang,et al.  Access to divergent benzo-heterocycles via a catalyst-dependent strategy in the controllable cyclization of o-alkynyl-N-methoxyl-benzamides. , 2017, Chemical communications.

[7]  Guanyinsheng Qiu,et al.  ZnBr2-Mediated oxidative spiro-bromocyclization of propiolamide for the synthesis of 3-bromo-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione. , 2017, Organic & biomolecular chemistry.

[8]  Fang Zhang,et al.  Copper-catalyzed borylative cyclization of 1,n-enynyl phosphates leading to five- to eight-membered cyclic 1,4-dienyl boronates , 2017 .

[9]  Gangguo Zhu,et al.  Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes. , 2017, Organic letters.

[10]  D. Gueyrard,et al.  Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B. , 2016, Organic letters.

[11]  Caroline E Hagerman,et al.  Phosphine-Triggered Selectivity Switch in Silver-Catalyzed o-Alkynylbenzohydroxamic Acid Cycloisomerizations. , 2016, Organic letters.

[12]  Liming Zhang,et al.  Au-Catalysed oxidative cyclisation. , 2016, Chemical Society reviews.

[13]  M. M. Heravi,et al.  Huisgen’s Cycloaddition Reactions: A Full Perspective , 2016 .

[14]  V. Boyarskiy,et al.  Alkenylation of Arenes and Heteroarenes with Alkynes. , 2016, Chemical reviews.

[15]  Q. Ding,et al.  Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone , 2016 .

[16]  H. Yoshida,et al.  Borylation of Alkynes under Base/Coinage Metal Catalysis: Some Recent Developments , 2016 .

[17]  Jie Wu,et al.  Generation of N-Heterocycles via Tandem Reactions of N '-(2-Alkynylbenzylidene)hydrazides. , 2016, Chemical record.

[18]  Jie Wu,et al.  Tandem metal-free oxidative radical 5-exo dearomative spirocyclization and ester migration: generation of 3-functionalized coumarins from alkynoates , 2016 .

[19]  S. Buchwald,et al.  Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes. , 2015, Angewandte Chemie.

[20]  Arghya Deb,et al.  The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil. , 2015, Chemical communications.

[21]  R. Álvarez,et al.  Palladium‐Catalyzed 6‐endo‐Selective Oxycyclization–Alkene Addition Cascades of ortho‐Alkynylarylcarboxamides and α,β‐Unsaturated Carbonyl Compounds , 2015 .

[22]  Y. Tu,et al.  Radical aryl migration reactions and synthetic applications. , 2015, Chemical Society reviews.

[23]  Q. Ding,et al.  Radical 5- exo cyclization of alkynoates with 2-oxoacetic acids for synthesis of 3-acylcoumarins , 2015 .

[24]  Jieping Zhu,et al.  2-(methoxycarbonyl)ethyl as a removable N-protecting group: synthesis of indoloisoquinolinones by Pd(II)-catalyzed intramolecular diamination of alkynes. , 2015, Organic letters.

[25]  D. Back,et al.  Nucleophilic Cyclization of o-Alkynylbenzamides Promoted by Iron(III) Chloride and Diorganyl Dichalcogenides: Synthesis of 4-Organochalcogenyl-1H-isochromen-1-imines , 2015 .

[26]  Y. Miwa,et al.  Regioselective iodoazidation of alkynes: synthesis of α,α-diazidoketones. , 2015, Organic letters.

[27]  K. Dev,et al.  Facile synthesis of 11-aryl-6H-isoindolo[2,1-a]indol-6-ones via hypervalent iodine(III)-promoted cascade cyclization , 2015 .

[28]  Xiao‐Ye Yu,et al.  Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles , 2014, Synthesis.

[29]  A. Sudalai,et al.  A simple and efficient synthesis of isocoumarins and alkylidenephthalides from 3-(1-hydroxycarbethoxy/alkyl)phthalides with a DEAD/PPh3/TBHP system , 2014 .

[30]  R. Álvarez,et al.  Palladium-Catalyzed Regioselective 5-exo-O-Cyclization/Oxidative Heck Cascades from o-Alkynylbenzamides and Electron-Deficient Alkenes† , 2014 .

[31]  P. Liu,et al.  Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide , 2014 .

[32]  J. D'Oyley,et al.  Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions , 2014, Angewandte Chemie.

[33]  H. Togo,et al.  Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide. , 2014, Organic letters.

[34]  Qing Jiang,et al.  K2S2O8-Mediated Difunctionalization of C≡C Bonds in Water: A Simple and Efficient Approach to α,α-Dihaloacetophenones from Phenylacetylenes and NaX , 2014 .

[35]  Fei Wang,et al.  Copper-mediated tandem oxidative C(sp2)-H/C(sp)-H alkynylation and annulation of arenes with terminal alkynes. , 2014, Organic letters.

[36]  B. Gabriele,et al.  Divergent palladium iodide catalyzed multicomponent carbonylative approaches to functionalized isoindolinone and isobenzofuranimine derivatives. , 2014, The Journal of organic chemistry.

[37]  W. Moran,et al.  Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions , 2014 .

[38]  L. Ackermann Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C-H/Het-H bond functionalizations. , 2014, Accounts of chemical research.

[39]  C. Nájera,et al.  Chemicals from alkynes with palladium catalysts. , 2014, Chemical reviews.

[40]  Jie Wu,et al.  Double carbometallation of alkynes: an efficient strategy for the construction of polycycles. , 2014, Chemical Society reviews.

[41]  Jie Wu,et al.  Synthesis of benzosultams via an intramolecular sp2 C-H bond amination reaction of o-arylbenzenesulfonamides under metal-free conditions. , 2014, Organic & biomolecular chemistry.

[42]  D. Bourissou,et al.  Metal–Ligand Cooperation in the Cycloisomerization of Alkynoic Acids with Indenediide Palladium Pincer Complexes , 2013 .

[43]  K. Kuo,et al.  A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one. , 2013, Organic & biomolecular chemistry.

[44]  Raveendra Jillella,et al.  A New and Efficient Method for the Synthesis of α,α-Dihaloketones by Oxyhalogenation of Alkynes Using Oxone®—KX (X: Cl, Br, or I). , 2013 .

[45]  A. Singh,et al.  Catalyst- and Metal-Free Rapid Functionalizations of Alkynes Using TsNBr2 , 2013 .

[46]  A. Fürstner Alkyne metathesis on the rise. , 2013, Angewandte Chemie.

[47]  H. Hussain,et al.  Journey describing applications of oxone in synthetic chemistry. , 2013, Chemical reviews.

[48]  U. Wille Radical cascades initiated by intermolecular radical addition to alkynes and related triple bond systems. , 2013, Chemical reviews.

[49]  R. Larock,et al.  Regio- and stereoselective synthesis of cyclic imidates via electrophilic cyclization of 2-(1-alkynyl)benzamides. A correction. , 2012, The Journal of organic chemistry.

[50]  D. Schollmeyer,et al.  Iodocyclization of o-alkynylbenzamides revisited: formation of isobenzofuran-1(3H)-imines and 1H-isochromen-1-imines instead of lactams. , 2012, The Journal of organic chemistry.

[51]  P. Wipf,et al.  Synthesis of a library of tricyclic azepinoisoindolinones , 2012, Beilstein journal of organic chemistry.

[52]  Jie Wu,et al.  An unexpected silver triflate-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with ketene. , 2012, Chemical communications.

[53]  Jieping Zhu,et al.  Palladium(II)-catalyzed intramolecular diamination of alkynes under aerobic oxidative conditions: catalytic turnover of an iodide ion. , 2012, Angewandte Chemie.

[54]  Jieping Zhu,et al.  Synergistic effect of palladium and copper catalysts: catalytic cyclizative dimerization of ortho-(1-alkynyl)benzamides leading to axially chiral 1,3-butadienes. , 2012, Chemistry.

[55]  Lei Liu,et al.  Phase-Transfer-Catalyzed Intramolecular Hydroaryloxylation and Hydroamination of C≡C Triple Bonds: An Efficient Synthesis of Benzo[ b ]furan and 3-Methyleneisoindoline-1-one Derivatives , 2011 .

[56]  Jie Wu,et al.  Palladium-catalyzed reaction of 2-alkynylhalobenzene with 2-alkynylbenzamide: an efficient approach to indeno[1,2-c]azepin-3(2H)-ones. , 2011, Chemical communications.

[57]  Zhiping Li,et al.  Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides , 2011 .

[58]  Wang-suo Wu,et al.  Regioselective Synthesis ofSubstituted Imidate N-[1-Methyleneisobenzofuran-3(1H)-ylidene]benzenamines viaPalladium-Catalyzed Tandem Heteroannulation of o-(1-Alkynyl)benzamides with Iodobenzene , 2011 .

[59]  O. Miyata,et al.  Copper(II)chloride-mediated cyclization reaction of N-alkoxy-ortho-alkynylbenzamides. , 2011, Organic letters.

[60]  R. Álvarez,et al.  A general synthesis of alkenyl-substituted benzofurans, indoles, and isoquinolones by cascade palladium-catalyzed heterocyclization/oxidative Heck coupling. , 2010, Chemistry.

[61]  Shin‐ichi Hirashima,et al.  Facile aerobic photo-oxidative syntheses of α,α-dibromoacetophenones from aromatic alkynes with 48% aq HBr , 2010 .

[62]  M. Chiarini,et al.  Product Selectivity Control in the Heteroannulation of o-(1-Alkynyl)benzamides , 2010 .

[63]  W. Yao,et al.  Highly efficient access to iminoisocoumarins and alpha-iminopyrones via AgOTf-catalyzed intramolecular enyne-amide cyclization. , 2010, The Journal of organic chemistry.

[64]  M. Terada,et al.  Dichotomous control of E/Z-geometry in intramolecular cyclization of o-alkynylbenzamide derivatives catalyzed by organic superbase P4-tBu in the presence/absence of water. , 2009, Chemistry, an Asian journal.

[65]  Hualiang Jiang,et al.  Silver‐Catalyzed Intramolecular Cyclization of o‐(1‐Alkynyl)benzamides: Efficient Synthesis of (1H)‐Isochromen‐1‐imines , 2009 .

[66]  R. Larock,et al.  Competition studies in alkyne electrophilic cyclization reactions. , 2009, The Journal of organic chemistry.

[67]  A. Wright,et al.  A New Antioxidant Isobenzofuranone Derivative from the Algicolous Marine Fungus Epicoccum sp. , 2003, Planta medica.

[68]  Y. Yu,et al.  Selective active site inhibitors of human lactate dehydrogenases A4, B4, and C4. , 2001, Biochemical pharmacology.

[69]  N. Kundu,et al.  Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones , 2000 .

[70]  A. Chappell,et al.  Reactions of Carbonyl-Conjugated Alkynes with N-Bromosuccinimide and N-Iodosuccinimide in DMF/H2O and Methanol/Sulfuric Acid: Syntheses of Dihalo Diketones, Dihalo Ketoesters, and Dihalo Acetals† , 1998 .

[71]  S. Young,et al.  Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds. , 1995, Journal of medicinal chemistry.

[72]  T. Inokuchi,et al.  Electrohalogenation of propargyl acetates and amides to form the 1,1-dibromo-2-oxo functionality and a facile synthesis of furaneol , 1992 .

[73]  E. Valencia,et al.  Magallanesine: an isoindolobenzazocine alkaloid , 1985 .