Copper catalyzed synthesis of seven and higher membered heterocycles

Abstract Nitrogen, oxygen, and sulfur-containing heterocycles have a wide range of biological activities. Metal catalysts are used in organic reactions with high activity. New methods have been explored for the synthesis of heterocyclic compounds in the past few years. The preparation of heterocycles with the assistance of metal catalyst is becoming a highly rewarding strategy in organic synthesis. In this review article, the synthesis of seven and higher-membered heterocycles is presented using copper as a catalyst. Graphical Abstract

[1]  Jie‐Ping Wan,et al.  Recent advances in copper-catalyzed C–H bond amidation , 2015, Beilstein journal of organic chemistry.

[2]  Lei Zhu,et al.  Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water , 2015, Beilstein journal of organic chemistry.

[3]  S. Chiba,et al.  Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines , 2015, Beilstein journal of organic chemistry.

[4]  N. Kaur.  Palladium-Catalyzed Approach to the Synthesis of S-heterocycles , 2015 .

[5]  N. Kaur.  Benign Approaches for the Microwave‐assisted Synthesis of Five‐membered 1,2‐N,N‐heterocycles , 2015 .

[6]  N. Kaur.  Role of Microwaves in the Synthesis of Fused Five-Membered Heterocycles with Three N-Heteroatoms , 2015 .

[7]  N. Kaur.  Environmentally Benign Synthesis of Five-Membered 1,3-N,N-Heterocycles by Microwave Irradiation , 2015 .

[8]  N. Kaur.  Microwave-Assisted Synthesis: Fused Five-Membered N-Heterocycles , 2015 .

[9]  Rui Yan,et al.  Total synthesis of herbimycin A. , 2014, Organic letters.

[10]  A. Behera,et al.  Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings , 2014 .

[11]  N. Kaur.  Metal catalysts: applications in higher-membered N-heterocycles synthesis , 2014, Journal of the Iranian Chemical Society.

[12]  K. El-bayouki.  Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications , 2013 .

[13]  B. Alcaide,et al.  Allenyl-β-lactams: versatile scaffolds for the synthesis of heterocycles. , 2011, Chemical record.

[14]  Yunyun Liu,et al.  Tandem reactions initiated by copper-catalyzed cross-coupling: a new strategy towards heterocycle synthesis. , 2011, Organic & biomolecular chemistry.

[15]  Yanguang Wang,et al.  One-pot synthesis of substituted indolines via a copper-catalyzed sequential multicomponent/C–N coupling reaction , 2011 .

[16]  Deepak K. Barange,et al.  One‐Pot Synthesis of Triazolothiadiazepine 1,1‐Dioxide Derivatives via Copper‐Catalyzed Tandem [3+2] Cycloaddition/N‐Arylation , 2011 .

[17]  T. Gorojankina,et al.  Design and synthesis of cyclic sulfonamides and sulfamates as new calcium sensing receptor agonists. , 2010, Bioorganic & medicinal chemistry letters.

[18]  S. Samanta,et al.  Alumina-supported Cu(II), a versatile and recyclable catalyst for regioselective ring opening of aziridines and epoxides and subsequent cyclization to functionalized 1,4-benzoxazines and 1,4-benzodioxanes. , 2010, The Journal of organic chemistry.

[19]  H. Kagechika,et al.  DESIGN AND SYNTHESIS OF NOVEL RETINOID SYNERGISTS HAVING A DIBENZODIAZEPINE SKELETON , 2010 .

[20]  Shou‐Fei Zhu,et al.  Enantioselective copper-catalyzed intramolecular O-H insertion: an efficient approach to chiral 2-carboxy cyclic ethers. , 2010, Journal of the American Chemical Society.

[21]  J. Saavedra,et al.  "Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors. , 2010, Organic letters.

[22]  Neeraj Kumar,et al.  Synthesis of chlorinated bicyclic C-fused tetrahydrofuro[3,2-c]azetidin-2-ones. , 2010, The Journal of organic chemistry.

[23]  马大为,et al.  Total Synthesis of Tetrahydroquinoline Alkaloid （＋）-Angustureine , 2010 .

[24]  Jinhua Dong,et al.  Iron(III)-catalyzed cyclization of alkynyl aldehyde acetals: experimental and computational studies. , 2010, Chemistry.

[25]  U. A. Kshirsagar,et al.  Copper-catalyzed intramolecular N-arylation of quinazolinones: facile convergent approach to (-)-circumdatins H and J. , 2010, Organic letters.

[26]  Liu Shi,et al.  Assembly of N-substituted pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via copper catalyzed aryl amination , 2010 .

[27]  Yunyun Liu,et al.  Copper-catalyzed tandem process: an efficient approach to 2-substituted-1,4-benzodioxanes. , 2010, Organic & biomolecular chemistry.

[28]  Luc Van Meervelt,et al.  Diversity-oriented synthesis of dibenzoazocines and dibenzoazepines via a microwave-assisted intramolecular A(3)-coupling reaction. , 2010, Organic letters.

[29]  S. Buchwald,et al.  Diamine Ligands in Copper-Catalyzed Reactions. , 2010, Chemical science.

[30]  S. Buchwald,et al.  Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions. , 2010, Journal of the American Chemical Society.

[31]  G. Sekar,et al.  Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes , 2010 .

[32]  G. Hammond,et al.  Highly efficient Cu(I)-catalyzed synthesis of N-heterocycles through a cyclization-triggered addition of alkynes. , 2010, Journal of the American Chemical Society.

[33]  Benjamin Willy,et al.  Three-component synthesis of benzo[b][1,5]thiazepines via coupling–addition–cyclocondensation sequence , 2010, Molecular Diversity.

[34]  Yongwen Jiang,et al.  Facile synthesis of 1,4-benzodiazepin-3-ones from o-bromobenzylamines and amino acids via a cascade coupling/condensation process , 2009 .

[35]  B. Alcaide,et al.  Generating complexity from simplicity: Pd-catalyzed or Cu-promoted domino alkyne homocoupling/double [2+2] allenyne cycloaddition. , 2009, Chemistry.

[36]  Miao Wang,et al.  Assembly of substituted 3-methyleneisoindolin-1-ones via a CuI/l-proline-catalyzed domino reaction process of 2-bromobenzamides and terminal alkynes. , 2009, Organic letters.

[37]  R. Andersen,et al.  Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues. , 2009, The Journal of organic chemistry.

[38]  Hongjian Lu,et al.  Copper-catalyzed intramolecular N-vinylation of sulfonamides: general and efficient synthesis of heterocyclic enamines and macrolactams. , 2008, The Journal of organic chemistry.

[39]  Benjamin Willy,et al.  Three-Component Synthesis of Cryofluorescent 2,4-Disubstituted 3H-1,5-Benzodiazepines – Conformational Control of ­Emission Properties , 2008 .

[40]  Benjamin Willy,et al.  Consecutive multi-component syntheses of heterocycles via palladium-copper catalyzed generation of alkynones , 2008 .

[41]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[42]  N. Fujii,et al.  Concise synthesis of indole-fused 1,4-diazepines through copper(I)-catalyzed domino three-component coupling-cyclization-N-arylation under microwave irradiation. , 2008, Organic letters.

[43]  J. Panek,et al.  Total synthesis of the Hsp90 inhibitor geldanamycin. , 2008, Organic letters.

[44]  R. Andersen,et al.  Synthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A. , 2008, Organic letters.

[45]  M. Martinelli,et al.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents. , 2007, Chemical reviews.

[46]  G. He,et al.  Total synthesis and stereochemistry assignment of 15-membered peptide alkaloids abyssenine B and mucronine E , 2007 .

[47]  T. Campo,et al.  Metal‐Catalyzed Regiodivergent Cyclization of γ‐Allenols: Tetrahydrofurans versus Oxepanes , 2007 .

[48]  F. Couty,et al.  Total synthesis of the cyclopeptide alkaloid abyssenine A. Application of inter- and intramolecular copper-mediated coupling reactions in organic synthesis. , 2007, The Journal of organic chemistry.

[49]  G. He,et al.  Highly convergent route to cyclopeptide alkaloids: total synthesis of ziziphine N. , 2007, Organic letters.

[50]  De‐Xian Wang,et al.  Highly efficient and stereoselective N-vinylation of oxiranecarboxamides and unprecedented 8-endo-epoxy-arene cyclization: expedient and biomimetic synthesis of some Clausena alkaloids. , 2007, Organic letters.

[51]  Y. Jahng,et al.  A versatile synthesis of cyclic diphenyl ether-type diarylheptanoids : Acerogenins, (±)-galeon, and (±)-pterocarine , 2007 .

[52]  K. Srinivasan,et al.  A novel one-pot three-component synthesis of 2,4-disubstituted-3 H-benzo[ b][1,4]diazepines in water , 2007 .

[53]  F. Couty,et al.  Total synthesis of paliurine F. , 2007, Angewandte Chemie.

[54]  Mark E. Scott,et al.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. , 2007, Chemical reviews.

[55]  F. Liu,et al.  A flexible route to immunosuppressive agent FR252921. Asymmetric total synthesis of its (13R,14R,19R)-isomer , 2006 .

[56]  Miriam Álvarez-Corral,et al.  Silver-catalyzed asymmetric synthesis of 2,3-dihydrobenzofurans: a new chiral synthesis of pterocarpans. , 2006, Chemistry.

[57]  Hongjian Lu,et al.  General and highly efficient synthesis of 2-alkylideneazetidines and beta-lactams via copper-catalyzed intramolecular N-vinylation. , 2006, Organic letters.

[58]  R. Hsung,et al.  Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocyclic ynamides. , 2006, The Journal of organic chemistry.

[59]  D. Ma,et al.  Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects. , 2006, Angewandte Chemie.

[60]  Alexander Dömling,et al.  Recent developments in isocyanide based multicomponent reactions in applied chemistry. , 2006, Chemical reviews.

[61]  Gwilherm Evano,et al.  Total synthesis of reblastatin. , 2005, Journal of the American Chemical Society.

[62]  Yuyang Jiang,et al.  Copper-catalyzed synthesis of medium- and large-sized nitrogen heterocycles via N-arylation of phosphoramidates and carbamates. , 2005, Organic letters.

[63]  Isamu Shiina,et al.  Total synthesis of buergerinin F via effective construction of the asymmetric quaternary carbons using an enantioselective aldol reaction. , 2005, Chemical communications.

[64]  Takao Inoue,et al.  Synthesis of photoactivatable acyclic analogues of the lobatamides. , 2005, The Journal of organic chemistry.

[65]  R. Hsung,et al.  Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (+/-)-desbromoarborescidines A and C. , 2005, Organic letters.

[66]  L. Zani,et al.  Iron-catalyzed reactions in organic synthesis. , 2004, Chemical reviews.

[67]  N. Zanatta,et al.  4-Alkoxy-1,1,1-trichloro-3-alken-2-ones: Preparation and Applications in Heterocyclic Synthesis , 2004 .

[68]  F. Liu,et al.  CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine. , 2004, Chemical communications.

[69]  F. Glorius,et al.  Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[70]  A. Couture,et al.  A new route to aristocularine alkaloids: total synthesis of aristoyagonine. , 2004, The Journal of organic chemistry.

[71]  J. Otera,et al.  Reversal of Chemoselectivity in Organotin Lewis Acid-Catalyzed Reaction of Ketene Silyl Acetal with Aldehyde and α-Enal , 2004 .

[72]  Artis Klapars,et al.  Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C-N bond formation-ring-expansion process. , 2004, Journal of the American Chemical Society.

[73]  G. Evano,et al.  A convergent synthesis of the macrocyclic core of cytotrienins: application of RCM for macrocyclization. , 2004, Organic letters.

[74]  M. Andrus,et al.  Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: asymmetric glycolate aldol reactions and biological evaluation. , 2003, The Journal of organic chemistry.

[75]  G. Molander,et al.  Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization. , 2003, The Journal of organic chemistry.

[76]  H. Ishikawa,et al.  Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids , 2003 .

[77]  M. Snapper,et al.  Total synthesis of anti-HIV agent chloropeptin I. , 2003, Journal of the American Chemical Society.

[78]  R. SanMartin,et al.  Revisiting the Ullmann-ether reaction: a concise and amenable synthesis of novel dibenzoxepino[4,5-d]pyrazoles by intramolecular etheration of 4,5-(o,o'-halohydroxy)arylpyrazoles. , 2002, The Journal of organic chemistry.

[79]  C. Frost,et al.  Silver phosphanes partnered with carborane monoanions: synthesis, structures and use as highly active Lewis acid catalysts in a hetero-Diels-Alder reaction. , 2002, Chemistry.

[80]  J. Porco,et al.  Total Synthesis and Stereochemical Assignment of the Salicylate Antitumor Macrolide Lobatamide C1 , 2002 .

[81]  B. Alcaide,et al.  Additions of allenyl/propargyl organometallic reagents to 4-oxoazetidine-2-carbaldehydes: novel palladium-catalyzed domino reactions in allenynes. , 2002, Chemistry.

[82]  R. S. Coleman,et al.  Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: organometallic coupling versus standard macrolactonization. , 2001, Organic letters.

[83]  D. Ma,et al.  CuI-catalyzed coupling reaction of beta-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction. Facile synthesis of SB-214857. , 2001, Organic letters.

[84]  M. A. Esteves,et al.  Synthetic derivatives of abietic acid with radical scavenging activity. , 2001, Journal of natural products.

[85]  C. Decicco,et al.  Intramolecular O-arylation of phenols with phenylboronic acids: application to the synthesis of macrocyclic metalloproteinase inhibitors. , 2001, Organic letters.

[86]  A. Padwa,et al.  An approach toward isoindolobenzazepines using the ammonium ylide/Stevens. , 2001, The Journal of organic chemistry.

[87]  A. Wells,et al.  Synthesis of SB-214857 using Copper Catalysed Amination of Arylbromides with l-Aspartic Acid , 2001 .

[88]  M. Doyle,et al.  Reactivities and selectivities in macrocyclic addition reactions with diazoacetates using copper(I) and rhodium(II) catalysts , 2000 .

[89]  Shen,et al.  Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution , 2000, Organic letters.

[90]  I. Paterson,et al.  Total Synthesis of (+)‐Concanamycin F , 2000 .

[91]  D. Lastécouères,et al.  New copper(I) and iron(II) complexes for atom transfer radical macrocyclisation reactions , 2000 .

[92]  I. Paterson,et al.  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction , 1999 .

[93]  V. Kalinin,et al.  Synthesis ofN-phenyl-substituted derivatives of morphine alkaloids , 1999 .

[94]  M. Calter,et al.  Orthoester condensation/CO insertion reaction sequence for the preparation of tetrahydrofurans , 1998 .

[95]  A. Padwa,et al.  An approach to the cephalotaxine ring skeleton using an ammonium ylide/Stevens [1, 2]-rearrangement , 1998 .

[96]  Feng Xu,et al.  CHIRAL CROTYLSILANE-BASED APPROACH TO BENZOQUINOID ANSAMYCINS : TOTAL SYNTHESIS OF (+)-MACBECIN I , 1998 .

[97]  Michael G. Yang,et al.  Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I: Application of Asymmetric Crotylsilane Bond Constructions , 1998 .

[98]  D. Lastécouères,et al.  New and improved catalysts for transition metal catalysed radical reactions , 1998 .

[99]  M. Doyle,et al.  Macrocyclic oxonium ylide formation and internal [2,3]-sigmatropic rearrangement catalyst influence on selectivity , 1997 .

[100]  R. Glazer,et al.  Modeling, chemistry, and biology of the benzolactam analogues of indolactam V (ILV). 2. Identification of the binding site of the benzolactams in the CRD2 activator-binding domain of PKCdelta and discovery of an ILV analogue of improved isozyme selectivity. , 1997, Journal of medicinal chemistry.

[101]  I. Paterson,et al.  Studies in macrolide synthesis: A novel cyclodimerisation approach to the synthesis of elaiophylin using a double Stille cross-coupling reaction , 1997 .

[102]  D. Wright,et al.  A METALLOCARBENOID APPROACH TO THE FORMATION OF SPIROCYCLIC AMMONIUM YLIDES LEADING TO THE PREPARATION OF MEDIUM-SIZED AZACANE RINGS , 1996 .

[103]  A. Itai,et al.  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins , 1996 .

[104]  K. Erhard,et al.  Enantiospecific synthesis of SB 214857, a potent, orally active, nonpeptide fibrinogen receptor antagonist , 1995 .

[105]  J. S. Clark,et al.  An enantioselective synthesis of the CE ring system of the alkaloids manzamine A, E and F, and ircinal a , 1995 .

[106]  D. Boger,et al.  Total Synthesis of Bouvardin, O-Methylbouvardin, and O-Methyl-N9-desmethylbouvardin , 1994 .

[107]  J. S. Clark,et al.  Intramolecular generation and rearrangement of ammonium ylides from copper carbenoids: a general method for the synthesis of cyclic amines , 1994 .

[108]  D. Boger,et al.  Total synthesis of (+)-Piperazinomycin , 1993 .

[109]  D. Boger,et al.  Total synthesis of cycloisodityrosine, RA-VII, deoxybouvardin, and N29-desmethyl-RA-VII: Identification of the pharmacophore and reversal of the subunit functional roles , 1993 .

[110]  D. Boger,et al.  Vancomycin and ristocetin models: synthesis via the Ullmann macrocyclization reaction , 1993 .

[111]  Scott J. Miller,et al.  Asymmetric synthesis of the benzoquinoid ansamycin antitumor antibiotics : total synthesis of (+)-macbecin , 1993 .

[112]  M. Nakata,et al.  Total Synthesis of Herbimycin A , 1991 .

[113]  D. Boger,et al.  Intramolecular ullmann condensation reaction : an effective approach to macrocyclic Diaryl Ethers , 1991 .

[114]  D. Boger,et al.  Total synthesis of deoxybouvardin and RA-VII: macrocyclization via an intramolecular Ullmann reaction , 1991 .

[115]  J. Castro,et al.  Total synthesis of (+)-macbecin I , 1990 .

[116]  E. Vedejs,et al.  Macrocycle synthesis by repeatable 2,3-sigmatropic shifts. Ring-growing reactions , 1975 .

[117]  Iram Goldberg.  Ueber Phenylirungen bei Gegenwart von Kupfer als Katalysator , 1906 .

[118]  F. Ullmann.  Ueber eine neue Bildungsweise von Diphenylaminderivaten , 1903 .