Journal of the Chemical Society. Perkin transactions I p. 691 - 696 (1988)
Update date:2022-08-06
Topics:
McFarlane, Michael D.
Moody, David J.
Smith, David M.
Cyclisation of N-(4- or 5-acylamino-2-nitrophenyl)glycine esters in basic media gives alkyl 5- or 6-acylaminobenzimidazole-2-carboxylate N-oxides, e.g. (11a) or (11b).Acid hydrolysis of the latter, followed by the reaction of ammonia, gives the title compounds (1b) and (1c), in acceptable yield.The corresponding reaction sequence with 4-acylamino-N-cyanomethyl-o-nitroanilines also gives (1b); where the acyl group is methylsulphonyl, however, the final product is 5-methanesulphonamidobenzimidazole N-oxide (9).Compound (1b) is also obtainable from ethyl 5-nitrobenzimidazole-2-carboxylate N-oxide by reduction followed by hydrolysis.Attempts to cyclise N-(o-nitrophenyl)glycine derivatives containing a free amino group at the 5-position are unsuccessful.This failure is attributed to mesomeric deactivation of the nitro group by the amino lone pair.
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