The Reaction of 2,4,6-Triphenyl-1,3-oxazinylium Perchlorate with Amino Compounds

Article abstract of DOI:10.1246/bcsj.54.2387

The reaction of 2,4,6-triphenyl-1,3-oxazinylium perchlorate with various kinds of amino compounds was studied.Primary amines and semicarbazides gave pyrimidinium perchlorates. o-Phenylenediamine, 0-aminobenzamide, and o-aminothiophenol afforded 2,4-diphenyl-1,5-benzodiazepine, 2-phenyl-4-hydroxyquinazoline, and 2-phenyl-1,3-benzothiazole respectively.Benzoylhydrazine, 4-pyridinecarbohydrazine, and 4-phenylthiosemicarbazide all led to pyrazoline derivatives.N,N-Dimethylhydrazine yielded two chain products competitively, while N,N'-dimethylhydrazine gave 1,2-dimethyl-3,5-diphenyl-1,2,4-triazolylium and 1,2-dimethyl-3,5-diphenyl-pyrazoly lium perchlorate competitively.It was thus shown that 2,4,6-triphenyl-1,3-oxazinylium perchlorate reacts with amino compounds in a complicated fashion to afford various heterocyclic compounds and other derivatives.