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2 H ‐1,2,4,6‐thiatriazin‐3(4 H )‐one 1‐oxides and their regioselective N 4 ‐methylation and ‐amination
Author(s) -
Nakayama Yoshinori,
Sanemitsu Yuzuru
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210562
Subject(s) - chemistry , diazomethane , regioselectivity , thionyl chloride , hydroxylamine , amination , medicinal chemistry , methylation , hydrazine (antidepressant) , chloride , organic chemistry , catalysis , biochemistry , chromatography , gene
The syntheses of 2 H ‐1,2,4,6‐thiatriazin‐3(4 H )‐one 1‐oxides and 1,1‐dioxides is described. The reaction of 1‐carbamoyl‐2‐methylisothioureas 2 with thionyl chloride gave 2 H ‐1,2,4,6‐thiatriazin‐3(4 H )‐one 1‐oxides 3 in high yields. The treatment of 3 with either diazomethane or O ‐(2,4‐dinitrophenyl)hydroxylamine furnished regioselectively N 4 ‐methylated and N 4 ‐aminated 2 H ‐1,2,4,6‐thiatriazin‐3(4 H )‐one 1‐oxides, respectively. Subsequent dimethylamination of 4 followed by oxidation with m ‐chloroperoxybenzoic acid led to 2 H ‐1,2,4,6‐thiatriazin‐3(4 H )‐one 1,1‐dioxides 6a‐c .
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