SYNTHESIS AND REGIOSELECTIVE [4-ARYLAMINO-1,3-DIAZA-1,3-BUTADIENES WITH KETENES AND ACCOMPANYING REARRANGEMENTS(2] CYCLOADDITION NUCLEOPHILIC REACTIONS OF N)
Pd. Dey et al., SYNTHESIS AND REGIOSELECTIVE [4-ARYLAMINO-1,3-DIAZA-1,3-BUTADIENES WITH KETENES AND ACCOMPANYING REARRANGEMENTS(2] CYCLOADDITION NUCLEOPHILIC REACTIONS OF N), Tetrahedron, 51(27), 1995, pp. 7459-7468
N-Arylamino-1,3-diaza-1,3-butadienes 4 are shown to undergo regioselec
tive reactions with phenyl- and chlorokete resulting in high yields of
3-aryl-2-methylthio-6-phenyl-4(3H)-pyrimidinones 7. Similar reactions
with bromo- and iodoketenes, resulted, via aziridinirum intermediates
12, in good yields of ylamino)-2-methylthio-6-phenyl-4(3H)-pyrimidino
nes 13. The mechanistic aspects of cycloadditions and semi-empirical A
M1 calculations for these diazabutadienes are also reported.