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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

The Influence of Base on Regioselectivity of 5-Substituted Uracils Addition to Michael Acceptors

Author(s): Slawomir Boncel and Krzysztof Walczak

Volume 3, Issue 7, 2006

Page: [534 - 538] Pages: 5

DOI: 10.2174/157017806778341942

Price: $65

Abstract

Michael type addition reaction of 5-substituted uracil derivatives to methyl acrylate and acrylonitrile has been studied. The regioselectivity of adducts has been observed due to the 5-substituent present in the uracil ring and the applied base. When triethylamine was used as a deprotonating agent, exclusively N-1 adducts were obtained. In the presence of DBU in DMF solution as the major products, N-3 adducts were isolated.

Keywords: 5-substituted uracils, Michael addition, methyl acrylate, acrylonitrile


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