Journal of Heterocyclic Chemistry

Acid??catalyzed cyclization of alkoxyacryloylureas to 2, 4 (1H, 3H) pyrimidinediones

YF Shealy, CA O'Dell

Index: Shealy,Y.F.; O'Dell,C.A. Journal of Heterocyclic Chemistry, 1976 , vol. 13, p. 1041 - 1047

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Citation Number: 37

Abstract

Abstract 1-Phenylthymine and the carbocyclic analog of thymidine were obtained in yields of 84-87% by cyclizing the appropriate 3-methoxy-2-methylacryloylureas in dilute sulfuric acid. High yields of 1-phenylthymine also resulted when the cyclization was carried out in trifluoroacetic acid, in acetic acid containing toluenesulfonic acid (TSA), or by fusion of the urea with a catalytic amount of TSA. In comparison, the typical aqueous-alkali catalyzed ...