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. Author manuscript; available in PMC: 2012 Jan 15.
Published in final edited form as: J Org Chem. 2005 Aug 5;70(16):6362–6368. doi: 10.1021/jo0508189

Table 3.

Substituent effect on the direction of ring closure to yield the [1,2,4]triazoles generated from unsymmetrical 1,3-disubstituted thioureas (General Procedure II)

graphic file with name nihms60552u3.jpg
R1 R2 % Yield
a Cyclohexyl Phenyl Urea
b Cyclohexyl 4-OMe-Phenyl 75(6b)
c 3,5-di-CF3-Phenyl Cyclohexyl 44(6c)
d Phenyl 4-OMe-Phenyl 76 (1:5)
e Phenyl 4-Cl-Phenyl 70 (2:3)
f 3,5-di-CF3-Phenyl Phenyl 84(6f)
g 3,5-di-CF3-Phenyl 4-OMe-Phenyl 77
h 3,5-di-CF3-Phenyl p-Tolyl 55
i 3,5-di-CF3-Phenyl o-Tolyl 50
j 3,5-di-CF3-Phenyl 2-i-Propyl-phenyl 45
k 3,5-di-CF3-Phenyl 2-t-Butyl-phenyl 8

Reaction times a – c = 48h and d – k = 2h