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The Journal of organic chemistry

Synthetic access to poly-substituted 6-alkoxyindoles from 1,3-cyclohexanediones and nitroolefins through facile aromatization reaction.


PMID 19894747

Abstract

6-Alkoxy-3-arylindoles were efficiently prepared from 1,3-cyclohexanedione enol ethers and beta-nitrostyrenes. Michael addition using the kinetically generated enolate, followed by Zn reduction of a nitro group of the resulting adducts produced the nitrones which were then treated with acetic anhydride to induce aromatization by dehydration and N-acetylation, which furnished the desired indoles by the DDQ oxidation. This methodology provides an easy entry toward various poly-substituted 6-alkoxyindoles.

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C101605
1,3-Cyclohexanedione, 97%
C6H8O2