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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 13
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Original Articles

Convenient Synthesis of 2-Vinylindoles

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Pages 2041-2047 | Received 25 Apr 1990, Published online: 24 Oct 2006
 

Abstract

A convenient, two-step synthesis of 2-vinylindoles is described from the easily accessible (E)-ethyl-α-allyl-2-nitrocinnamates. Ethylcinnamates (1a and 1b) on reaction with triethylphosphite provide ethyl-2-allylindole-3carboxylates (2a and 2b ) along with minor amounts of their N-ethoxyderivatives (4a and 4b). Alkaline hydrolysis of 2a and 2b provide (E)-2-vinylindoles 3a and 3b in 60 and 67% yield respectively.

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