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

Author(s): Slawomir Boncel, Krzysztof Walczak.

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 7 , 2006

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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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Article Details

Year: 2006
Page: [534 - 538]
Pages: 5
DOI: 10.2174/157017806778341942
Price: $58

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