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Scope of a Novel Three-Component Synthesis of Highly Functionalized Pyridines†
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Abstract
A mechanistically unique three-component synthesis provides a variety of functionalized pyridine derivatives in fair to excellent yields. The scope of this reaction was studied with respect to the alkoxyallene, the nitrile, and the carboxylic acid. Due to the 4-hydroxy group, these pyridine derivatives are suitable precursors for subsequent palladium-catalyzed reactions. Suzuki couplings of the corresponding pyridyl nonaflates lead to a variety of pyridine and bipyridine derivatives.
Citing Articles
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
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 ...
Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines
Timothy J. Donohoe, José A. Basutto, John F. Bower, and Akshat RathiOrganic Letters2011 13 (5), 1036-1039Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines
Timothy J. Donohoe, José A. Basutto, John F. Bower, and Akshat RathiOrganic Letters2011 13 (5), 1036-1039The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of α,β-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono−tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl ...
Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling Reactions
Tilman Lechel, Jyotirmayee Dash, Paul Hommes, Dieter Lentz and Hans-Ulrich ReissigThe Journal of Organic Chemistry2010 75 (3), 726-732Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling Reactions
Tilman Lechel, Jyotirmayee Dash, Paul Hommes, Dieter Lentz and Hans-Ulrich ReissigThe Journal of Organic Chemistry2010 75 (3), 726-732A three-component reaction with lithiated alkoxyallenes, nitriles, and perfluorinated carboxylic acids as precursors led to a series of perfluoroalkyl- or perfluoroaryl-substituted 4-hydroxypyridine derivatives. These compounds were converted into 4-...
Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
Yi-Feng Wang and Shunsuke ChibaJournal of the American Chemical Society2009 131 (35), 12570-12572Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
Yi-Feng Wang and Shunsuke ChibaJournal of the American Chemical Society2009 131 (35), 12570-12572A Mn(III)-mediated divergent synthesis of substituted pyridines and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives was exploited using readily available vinyl azides and cyclopropanols with a wide range of substituents. In short, the reactions of vinyl ...
Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes
Malte Brasholz, Hans-Ulrich Reissig and Reinhold ZimmerAccounts of Chemical Research2009 42 (1), 45-56Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes
Malte Brasholz, Hans-Ulrich Reissig and Reinhold ZimmerAccounts of Chemical Research2009 42 (1), 45-56As master craftsmen, modern synthetic chemists are challenged to achieve remarkable feats of efficiency and elegance toward molecular targets. The nature of this pursuit necessitates the collection of synthetic repertoires that are tried and true. With ...
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History
- Published In Issue December 20, 2007
- Received October 12, 2007
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