Literature DB >> 25332116

Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Yi Shi1, Anton V Gulevich, Vladimir Gevorgyan.   

Abstract

A general and efficient NH insertion reaction of rhodium pyridyl carbenes derived from pyridotriazoles was developed. Various NH-containing compounds, including amides, anilines, enamines, and aliphatic amines, smoothly underwent the NH insertion reaction to afford 2-picolylamine derivatives. The developed transformation was further utilized in a facile one-pot synthesis of imidazo[1,5-a]pyridines.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulations; carbenes; heterocycles; rhodium; synthetic methods

Mesh:

Substances:

Year:  2014        PMID: 25332116      PMCID: PMC4262672          DOI: 10.1002/anie.201408335

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  39 in total

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Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
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5.  Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles.

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Authors:  Stepan Chuprakov; Sen Wai Kwok; Valery V Fokin
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8.  Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Authors:  Nicklas Selander; Brady T Worrell; Stepan Chuprakov; Subash Velaparthi; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-08-28       Impact factor: 15.419

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Journal:  Org Lett       Date:  2014-04-07       Impact factor: 6.005

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  6 in total

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4.  Light-induced metal-free transformations of unactivated pyridotriazoles.

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5.  Mg3N2-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine.

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Journal:  RSC Adv       Date:  2020-03-23       Impact factor: 4.036

6.  Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.

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  6 in total

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