SYNTHESIS OF 2H-PYRROLES AND PYRROLES - REACTION OF CARBANIONS WITH 2H-AZIRINES OR N,N,N-TRIMETHYLHYDRAZONIUM SALTS

Dimsyl sodium reacts with 2H-azirines 2 to give amino ethylenic sulfoxide 5E. The same reaction is observed from N,N,N-trimethylhydrazonium salt 1 using an excess of dimsylsodium. Carbanions of ketone or nitrile react with 2H-azirine or N,N,N-trimethylhydrazonium to produce 2H-pyrroles 6-13, 20 or pyrroles 18, 19. This reaction is the most convenient general route to 2H-pyrroles. © 1979.