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The Journal of organic chemistry

A new, stereoselective, ring-forming reaction of 1,2-ethanedithiol with N-acylated indoles.


PMID 17941672

Abstract

While attempting to prepare 2,5-dithiacyclopentyl derivatives from N-acyl 5-fluoroindole by reaction with 1,2-ethanedithiol we discovered that, instead of the expected product, annelation occurred to give a tricyclic compound containing a 3,6-dithiaazepine ring. This reaction is stereoselective and was found to be general for N-acylindoles, not being affected by substituents on the indole ring.

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