Isao Shibuya
1981
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
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, o-aminobenzamide, and o-aminothiophenol afforded 2,4-diphenyl-1,5-benzodiazepine, 2-phenyl-4-hydroxyquinazoline, and 2-phenyl-1,3-benzothiazole respectively. Benzoylhydrazine, 4-pyridinecarbohydrazide, 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-diphenylpyrazolylium 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.