Addition reactions of azoesters with 2-thioquinazolinones

Reaction between diethyl azodicarboxylate (I) and 1,2,3,4-tetrahydro-2-thioquinazolin-4-one (II), as a cyclic model of thiourea, both in alcoholic medium and in inert solvents has been investigated. By carrying out the reaction in an inert solvent, it was possible to isolate an intermediate. Evidence is presented that the intermediate, in turn, was converted into the final products. Structures were unequivocally assigned by mass spectrometry.