A new indole synthesis via [3+3] annulation of 2-(benzotriazol-1-ylmethyl)-pyrroles with α,β-unsaturated aldehydes and ketones

Alan R Katritzky; Julian R Levell; Jianqing Li

doi:10.1016/0040-4039(96)01216-6

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A new indole synthesis via [3+3] annulation of 2-(benzotriazol-1-ylmethyl)-pyrroles with α,β-unsaturated aldehydes and ketones

Journal article

Peer reviewed

A new indole synthesis via [3+3] annulation of 2-(benzotriazol-1-ylmethyl)-pyrroles with α,β-unsaturated aldehydes and ketones

Alan R Katritzky, Julian R Levell and Jianqing Li

Tetrahedron letters, Vol.37(32), pp.5641-5644

05/08/1996

DOI: https://doi.org/10.1016/0040-4039(96)01216-6

Abstract

Poly-substituted indoles are readily accessible from substituted 2-(benzotriazol-1-ylmethyl)pyrrobles by lithiation, reaction with α,β-unsaturated aldehydes and ketones, and subsequent facile dehydrobenzotriazolylation-cyclodehydration. The substituted 2-(benzotriazol-1-ylmethyl)-pyrrole precursors are obtained by reacting α-bromoketones with terminally lithiated propargylbenzotriazole, and treating the resulting epoxide with a primary amine. Graphic

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Title: A new indole synthesis via [3+3] annulation of 2-(benzotriazol-1-ylmethyl)-pyrroles with α,β-unsaturated aldehydes and ketones
Creators - without role: Alan R Katritzky - University of Florida
Julian R Levell - University of Florida
Jianqing Li - University of Florida
Publication Details: Tetrahedron letters, Vol.37(32), pp.5641-5644
Publisher: Elsevier Ltd
Identifiers: 9934884208331
Academic Unit: King Abdulaziz University
Language: English
Resource Type: Journal article