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Org Biomol Chem. 2016 Jun 28;14(24):5586-90. doi: 10.1039/c6ob00501b. Epub 2016 Mar 24.

Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet-Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates.

Organic & biomolecular chemistry

Santosh J Gharpure, Santosh K Nanda

Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India. [email protected].

PMID: 27011230 DOI: 10.1039/c6ob00501b

Abstract

An inter- as well as intra-molecular thia-Pictet-Spengler cyclization of N-tethered thiols and vinylogous thiocarbonates is described for the stereoselective synthesis of N-fused thiazinoindole derivatives. The strategy is extended to one-pot, sequential Friedel-Crafts alkylation - Pictet-Spengler cyclization and the synthesis of thiazino-oxepino-indole.

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