The chemistry of N-substituted benzotriazoles. Part 20. Mono-N-t-butylation of aromatic and heteroaromatic amines

Abstract

Adducts R¹CH(Bt)NHAr, readily available from aldehydes, primary aromatic or heteroaromatic amines, and benzotriazole are converted by H₂O₂–SeO₂ into mixtures of R¹CONHAr and HCONR¹Ar in proportions which depend rationally on the nature of the R¹ group. For R¹= Bu^t, the formamide HCON(Bu^t)Ar is formed in satisfactory yields thus enabling the title reaction to be achieved.