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Direct Synthesis of Pyridine Derivatives
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Abstract
We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyridine and quinoline derivatives, respectively. The process involves amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by π-nucleophile addition to the activated intermediate and annulation. Compatibility of this chemistry with sensitive N-vinyl amides, epimerizable substrates, and a variety of functional groups is noteworthy.
Citing Articles
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This article has been cited by 28 ACS Journal articles (5 most recent appear below).
Synthesis of δ-Carbolines via a Pd-Catalyzed Sequential Reaction from 2-Iodoanilines and N-Tosyl-enynamines
Jian Cao, Yongping Xu, Yulong Kong, Yuming Cui, Ziqiang Hu, Guanhai Wang, Yuan Deng, and Guoqiao LaiOrganic Letters2012 14 (1), 38-41Synthesis of δ-Carbolines via a Pd-Catalyzed Sequential Reaction from 2-Iodoanilines and N-Tosyl-enynamines
Jian Cao, Yongping Xu, Yulong Kong, Yuming Cui, Ziqiang Hu, Guanhai Wang, Yuan Deng, and Guoqiao LaiOrganic Letters2012 14 (1), 38-41A facile Pd-catalyzed sequential reaction has been developed for the synthesis of δ-carbolines from 2-iodoanilines and N-tosyl-enynamines. This protocol involves Larock heteroannulation/elimination/electrocyclization/oxidative aromatization cascade ...
Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes
Yu Sung Chun, Jun Hee Lee, Ju Hyun Kim, Young Ok Ko, and Sang-gi LeeOrganic Letters2011 13 (24), 6390-6393Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes
Yu Sung Chun, Jun Hee Lee, Ju Hyun Kim, Young Ok Ko, and Sang-gi LeeOrganic Letters2011 13 (24), 6390-6393A tandem one-pot method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective ...
Copper-Catalyzed Coupling of Oxime Acetates with Aldehydes: A New Strategy for Synthesis of Pyridines
Zhi-Hui Ren, Zhi-Yuan Zhang, Bing-Qin Yang, Yao-Yu Wang, and Zheng-Hui GuanOrganic Letters2011 13 (19), 5394-5397Copper-Catalyzed Coupling of Oxime Acetates with Aldehydes: A New Strategy for Synthesis of Pyridines
Zhi-Hui Ren, Zhi-Yuan Zhang, Bing-Qin Yang, Yao-Yu Wang, and Zheng-Hui GuanOrganic Letters2011 13 (19), 5394-5397Copper-catalyzed coupling of oxime acetates with aldehydes offers a new strategy for the synthesis of highly substituted pyridines. This novel method tolerates a wide range of functionality and allows for rapid elaboration of the oxime acetates into a ...
Cascade Reaction of Isatins with Heterocyclic Ketene Aminals: Synthesis of Imidazopyrroloquinoline Derivatives
Fuchao Yu, Shengjiao Yan, Ling Hu, Yongchao Wang, and Jun LinOrganic Letters2011 13 (18), 4782-4785Cascade Reaction of Isatins with Heterocyclic Ketene Aminals: Synthesis of Imidazopyrroloquinoline Derivatives
Fuchao Yu, Shengjiao Yan, Ling Hu, Yongchao Wang, and Jun LinOrganic Letters2011 13 (18), 4782-4785A concise and efficient route for the synthesis of highly substituted imidazopyrroloquinoline derivatives by simply refluxing a reaction mixture of different types of isatins and heterocyclic ketene aminals (HKAs) by acetic acid was developed. This method ...
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 ...
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History
- Published In Issue August 22, 2007
- Received May 30, 2007
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