N-Arylamino-1:3-diaza-1:3-butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12, in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13, The mechanistic aspects of cycloadditions and semi-empirical AM1 calculations for these diazabutadienes are also reported.
|Original language||English (US)|
|Number of pages||10|
|State||Published - Jul 3 1995|
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry