A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(ii)/copper(ii) catalytic sequence

We report herein a sequential bicatalytic route to provide a versatile access to a wide range of synthetically useful nitrogen-containing heterocycles in a single pot from furan and aniline derivatives. This transformation relies on an aza-Piancatelli/hydroamination sequence promoted by common calci...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2018-01, Vol.5 (4), p.640-647
Main Authors: Marin, L, Guillot, R, Gandon, V, Schulz, E, Lebœuf, D
Format: Article
Language:English
Subjects:
Aniline
Aromatic compounds
Calcium
Calcium compounds
Catalysis
Chemical Sciences
Copper
Copper compounds
Nitrogen
Organic chemistry
Pyrroles
Quinoxalines
Salts
Synthesis
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Summary:We report herein a sequential bicatalytic route to provide a versatile access to a wide range of synthetically useful nitrogen-containing heterocycles in a single pot from furan and aniline derivatives. This transformation relies on an aza-Piancatelli/hydroamination sequence promoted by common calcium(ii) and copper(ii) salts. Depending on the substitution pattern of the precursors as well as the solvent employed, this method enables the preparation of biologically relevant molecules such as cyclopenta[b]pyrroles, pyrrolo[1,2-a]quinoxalines and also a novel class of cyclopenta[b]pyrrolines. Moreover, the first atropodiastereoselective synthesis of N-aryl cyclopenta[b]pyrroles is described.
ISSN:2052-4110
2052-4110
DOI:10.1039/c7qo00948h