Facile Routes to Alkoxymaleimides/Maleic Anhydrides

Manoj Kumar Sahoo; Santosh B. Mhaske; Narshinha P. Argade

doi:10.1055/s-2003-37351

PAPER

Facile Routes to Alkoxymaleimides/Maleic Anhydrides [1]

Manoj Kumar Sahoo, Santosh B. Mhaske, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)5893153; e-Mail: argade@dalton.ncl.res.in;

Abstract

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Abstract

New routes to alkoxymaleic anhydrides 1a/b have been described in good yields via base-induced chemoselective vinylic substitution of bromo atom in bromomaleimide 4 with alkanols, and base-induced oxa-Micahel addition of alkanols to dialkyl acetylenedicarboxylates 8a/b as key steps. An unusual acyl exchange in the conversion of 6a/b to 1a/b under very simple and mild reaction conditions is noteworthy.

Key words

bromomaleimide - dialkyl acetylenedicarboxylates - oxa-Michael additions - alkoxymaleic anhydrides

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