REGIOSELECTIVE [4-ARYLAMINO SUBSTITUTED 1,3-DIAZA-1,3-BUTADIENES WITHKETENES - SYNTHESIS OF PYRIMIDINONE AND FUSED PYRIMIDINONE DERIVATIVES .2.(2]CYCLOADDITION VERSUS NUCLEOPHILIC REACTIONS OF N)
Pd. Dey et al., REGIOSELECTIVE [4-ARYLAMINO SUBSTITUTED 1,3-DIAZA-1,3-BUTADIENES WITHKETENES - SYNTHESIS OF PYRIMIDINONE AND FUSED PYRIMIDINONE DERIVATIVES .2.(2]CYCLOADDITION VERSUS NUCLEOPHILIC REACTIONS OF N), Tetrahedron, 53(40), 1997, pp. 13829-13840
A novel synthetic method for 3-aryl-6-phenyl-2-methylthio/secondaryami
no substituted-4(3H)-pyrimidinones 5 and 9 by the reactions of N-aryla
mino substituted 1,3-diaza-1,3-butadienes 1 and 6 with phenyl-, vinyl-
and isopropenylketenes is explored. Semi emperical AMI calculations on
1 and 6 are performed to explain the mechanism of their reaction with
ketenes. Transformations of 5 and 9 leading to fused pyrimidinones 10
are also reported. (C) 1997 Elsevier Science Ltd.