Reaction of Β-arylacrylyloxiranes with amidines

✍ Scribed by A. M. Zvonok; N. M. Kuz'menok

• Book ID: 104785718
• Publisher: Springer US
• Year: 1990
• Tongue: English
• Weight: 471 KB
• Volume: 26
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00487432

✦ Synopsis

Mixtures of stereoisomers of oxiranylhydroxytetrahydropyrimidines were obtained by cyclocondensation of a-arylacrylyloxiranes with acetamidines or benzamidines; the 2-aryl derivatives of the products give the corresponding dihydropyrimidines and pyrimidines under base-catalysis conditions~ In acetic acid dehydration and oxidation are accompanied by opening of the epoxide ring.

The important role of pyrimidine derivatives in biological processes is responsible for the interest of researchers in the chemistry of this class of compounds [1][2][3]. The aim of the present research was the synthesis of new derivatives of the pyrimidine series that contain an epoxide ring in the side chain, which opens up extensive possibilities for subsequent functiormliTation.

The reaction of t~-arylacrylyloxiranes Ia-c with acetamidines or benzamidines leads to mixtures of stereoisomeric 4(6)hydroxy-2-methyl(phenyl)-6(4)-aryl-4(6)-1,2-cpoxyallojl-1,4,5,6-tctrahydropyrimidines IIa-c and IIIa--c in good yields. CH. H " o o . w ~ Ia-c_ o lla-c; llla-c Ph 11