IMINIUM CARBONIC-ACID DERIVATIVE SALTS .10. SYNTHESIS OF N,S-CONTAINING HETEROBICYCLES FROM N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS .2. REACTION OF N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS WITH VINYLOGOUS CH-ACIDICCOMPOUNDS
W. Hanefeld et al., IMINIUM CARBONIC-ACID DERIVATIVE SALTS .10. SYNTHESIS OF N,S-CONTAINING HETEROBICYCLES FROM N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS .2. REACTION OF N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS WITH VINYLOGOUS CH-ACIDICCOMPOUNDS, Journal of heterocyclic chemistry, 33(6), 1996, pp. 1791-1796
N-Boc-protected 2-methylthio-1,3-thiazinium 3 and 2-methylthiothiazoli
um salts 4,7 obtained from the corresponding 1,3-thiazine-2-thiones an
d thiazolidine-2-thiones by the action of methyl iodide or trimethylox
onium tetrafluoroborate were reacted with vinylogous CH-acidic compoun
ds forming ketene N,S-acetals 5,6,8,9. The protection group was remove
d with trifluoroacetic acid whereupon the desired cyclisation to pyrid
o[2,1-bl-1,3-thiazines 10 and thiazolo[3,2-b]pyridines 11,12 took plac
e.