Tetrahedron

Reactions with α-substituted cinnamonitriles: A novel synthesis of arylpyrimidines

AM Abd-Elfattah, SM Hussain, AM El-Reedy, NM Yousif

Index: Abd-Elfattah, A. M.; Hussain, S. M.; El-Reedy, A. M.; Yousif, N. M. Tetrahedron, 1983 , vol. 39, # 19 p. 3197 - 3199

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Citation Number: 17

Abstract

α-Benzoyl-and α-ethoxycarbonylcinnamonitrile derivatives 1a-c and ld-f reacted with benzamidine hydrochloride (2) in boiling pyridine to give the fully aromatized aryl-pyrimidine derivatives 3a-c and 6a-c respectively. In contrast the a-cyanocinnamonitrile derivatives 1g-j reacted with 2 under the same conditions to form the dihydropyrimidine derivatives 7a-d. Compounds 7a, b could be dehydrogenated to the fully aromatized analogues 8a, b as ...