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Synthesis of Polysubstituted N-H Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds
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Abstract
Two synthetic methods for tetra- and trisubstituted N-H pyrroles are presented: (i) the thermal pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from α-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods, regioisomeric pyrroles can be prepared selectively starting from the same vinyl azides.
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).
Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen WangOrganic Letters2011 13 (24), 6362-6365Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen WangOrganic Letters2011 13 (24), 6362-6365A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, ...
Three-Component Synthesis of Polysubstituted Pyrroles from α-Diazoketones, Nitroalkenes, and Amines
Deng Hong, Yuanxun Zhu, Yao Li, Xufeng Lin, Ping Lu, and Yanguang WangOrganic Letters2011 Article ASAPThree-Component Synthesis of Polysubstituted Pyrroles from α-Diazoketones, Nitroalkenes, and Amines
Deng Hong, Yuanxun Zhu, Yao Li, Xufeng Lin, Ping Lu, and Yanguang WangOrganic Letters2011 Article ASAPPolysubstituted pyrroles are regiospecifically synthesized via the copper-catalyzed three-component reaction of α-diazoketones, nitroalkenes, and amines under aerobic conditions. The cascade process involves an N–H insertion of carbene, a copper-catalyzed ...
Diamine-Catalyzed Conjugate Addition to Acrylate Derivatives
Benny Meng Kiat Tong and Shunsuke ChibaOrganic Letters2011 Article ASAPDiamine-Catalyzed Conjugate Addition to Acrylate Derivatives
Benny Meng Kiat Tong and Shunsuke ChibaOrganic Letters2011 Article ASAPDiamines were found to promote catalytic conjugate addition of α-cyano active methine nucleophiles to various acrylate derivatives.
Mn(III)-Mediated Formal [3+3]-Annulation of Vinyl Azides and Cyclopropanols: A Divergent Synthesis of Azaheterocycles
Yi-Feng Wang, Kah Kah Toh, Eileen Pei Jian Ng, and Shunsuke ChibaJournal of the American Chemical Society2011 133 (16), 6411-6421Mn(III)-Mediated Formal [3+3]-Annulation of Vinyl Azides and Cyclopropanols: A Divergent Synthesis of Azaheterocycles
Yi-Feng Wang, Kah Kah Toh, Eileen Pei Jian Ng, and Shunsuke ChibaJournal of the American Chemical Society2011 133 (16), 6411-6421Mn(III)-mediated formal [3+3]-annulation has been developed using readily available vinyl azides and cyclopropanols with a wide range of substituents. Vinyl azides were successfully applied as a three-atom unit including one nitrogen to prepare pyridines ...
Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides
Benjamin J. Stokes, Sheng Liu, and Tom G. DriverJournal of the American Chemical Society2011 133 (13), 4702-4705Rh2(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides
Benjamin J. Stokes, Sheng Liu, and Tom G. DriverJournal of the American Chemical Society2011 133 (13), 4702-4705Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from β-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester
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History
- Published In Issue January 17, 2008
- Received November 10, 2007
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