
TY  - JOUR
A1  - Ali, Abdelselam S. 
A1  - Wilkie, John S. 
A1  - Winzenberg, Kevin N. 
T1  - Synthesis of Some 1<emph type="2">H</emph>-1,2,4-Triazole, 4<emph type="2">H</emph>-1,2,4-Triazole, Thiazolo[2,3-<emph type="2">c</emph>]-1,2,4-triazole and 5<emph type="2">H</emph>-1,2,4-Triazolo-[3,4-<emph type="2">b</emph>][1,3]thiazine Derivatives by Metal Compound-Mediated Oxidative Cyclization of Derivatives of 2-(Phenylmethylidene)hydrazinecarboximidothioic Acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 9
SP  - 911
EP  - 916
KW  - 
UR  - https://doi.org/10.1071/C97058 
N2  - Reaction of the methyl 2-(phenylmethylidene)hydrazinecarboximidothioate derivatives (3a&#8211;d) and (6a,b) with iron(III) chloride afforded the 5-methylsulfanyl-3-phenyl-4H-1,2,4-triazole derivatives (4a&#8211;d) and the 5-methylsulfanyl-3-phenyl-1H-1,2,4-triazole derivatives (7a,b). This reaction was extended to the synthesis of the 3-phenyl-5,6-dihydrothiazolo&#91;2,3-c&#93;-1,2,4-triazole derivatives (10a,b) and the 3-phenyl-6,7-dihydro-5H-1,2,4-triazolo&#91;3,4-b&#93;&#91;1,3&#93;thiazine derivatives (10c,d). Reaction of 5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (12a) with 1,2-dibromoethane gave (10a) together with the isomeric 2-(3-chlorophenyl)-5,6-dihydrothiazolo&#91;3,2-b&#93;&#91;1,2,4&#93;triazole (13a); similarly, reaction of (12a) with 1,3-dibromopropane afforded (10c) along with 2-(3-chlorophenyl)-6,7-dihydro-5H-&#91;1,2,4&#93;triazolo&#91;5,1-b&#93;&#91;1,3&#93;thiazine (13b). The use of nickel peroxide and lead tetraacetate in place of iron(III) chloride was investigated for some of these oxidative cyclization reactions. 
ER  -

