3-Amino-1-[2-(2-ethoxyethoxy)ethoxy ] benzo[∫]quinazoline

The structure of an anomalous product, isolated as a companion substance during the catalytic dehydrogenation of 1,3-diamino-5,6-dihydrobenzo[?] quinazoline, has been elucidated with the aid of chemical and spectral evidence, including mass spectrometric data. The mass spectrometric fragmentation pattern of the compound is in good agreement with the assigned structure.     

Isomerization of N-[α-(Alkylthio)alkyl]- and N-[α-(Arylthio)alkyl]benzotriazoles

The thermal isomerizations of N-[α-(alkylthio)alkyl]- and N-[α-(arylthio)alkyl]benzotriazoles have been investigated under N₂ atmospheres (i) in toluene, xylene, MeOH, or EtOH, in the presence of acid catalysts and (ii) in the absence of solvent. The sulfide isomerization rates depend on the number of H-atoms carried by the C-atom attached to the N-atom of the benzotriazole: tertiary (no hydrogen) > secondary (1 hydrogen) > primary (2 hydrogens). The results support an isomenzation mechanism involving a heterolytic N? C bond cleavage with formation of sulfonium/carbonium and benzotriazolate ions.