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

Slawomir      Boncel; Krzysztof      Walczak

doi:10.2174/157017806778341942

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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Letters in Organic Chemistry

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

Volume: 3 Issue: 7

Author(s): Slawomir Boncel and Krzysztof Walczak

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

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.

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Boncel Slawomir and Walczak Krzysztof, The Influence of Base on Regioselectivity of 5-Substituted Uracils Addition to Michael Acceptors, Letters in Organic Chemistry 2006; 3 (7) . https://dx.doi.org/10.2174/157017806778341942