QUINONE-IMIDES : REGIOSPECIFICITY OF NUCLEOPHILIC ATTACK ON N-ALKANESULPHONYL-N'-ALKANOYL 1,4-BENZOQUINONE-IMINES.

Article abstract of DOI:10.1016/S0040-4020(01)88179-5

Substrates such as (2) undergo regiospecific attack by azide and thiocyanate ions at the terminus of the C=C-C=N-CO system.In the case of addition of azide, this is proved by the detailed analysis of the 1H and 13C NMR spectra of the products (11) derived from the quinone-imides (8).The structure of the products obtained by the addition of thiocyanate to the quinone-imides (10) and (20) is proved by their facile cyclisation to the 2-aminobenzothiazoles (18) and (21) respectively.