The reaction of 2,4,6-triphenyl-1,3-oxazinylium perchlorate with amino compounds.
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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. <I>o</I>-Phenylenediamine, <I>o</I>-aminobenzamide, and <I>o</I>-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. <I>N</I>,<I>N</I>-Dimethylhydrazine yielded two chain products competitively, while <I>N</I>,<I>N</I>′-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.
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