Benzimidazoles containing bulky 2-substituents, e.g. adamantyl and t-butyl, have been synthesized by condensation of o-phenylenediamines with carboxylic acids at hydrostatic pressures of up to 8 kbar. Attempts to make the analogous benzothiazoles and benzoxazoles at high pressures were unsuccessful, but an alternative synthesis was devised. A novel diazepinone (18) is reported.
G. Holan, J. J. Evans and M. Linton, J. Chem. Soc., Perkin Trans. 1, 1977, 1200 DOI: 10.1039/P19770001200
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