One-step synthesis of diazadihydroacenaphthylene derivatives with an isoxazoline ring, starting from 1-benzylamino-1-methylsulfanyl-2-nitroethenes

At low temperature in trifluoromethanesulfonic acid, 1-benzylamino-1-methylthio-2-nitroethene derivatives form hydroxynitrilium ions (or O-protonated nitrile oxides) observed by NMR. Quenching with water leads to the formation of a reactive nitrile oxide, dipole which undergoes an unexpected INOC reaction leading to new 3-methylsulfanyl-8a,8b-dihydro-5H-1-oxa-2,4-diazaacenaphthylenes. (c) 2006 Elsevier Ltd. All rights reserved.