Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 2, pp. 230−235.
Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.M. Chernyshov, G.V. Kozlenko, V.A. Taranushich, 2011, published in Zhurnal Prikladnoi Khimii, 2011, Vol. 84, No. 2, pp. 234−239.
AND INDUSTRIAL ORGANIC CHEMISTRY
Regioselective Single-Reactor Synthesis
of Arylsulfonyl Derivatives of 3,5-Diamino-1,2,4-triazole
V. M. Chernyshov, G. V. Kozlenko, and V. A. Taranushich
South-Russian State Technical University (Novocherkassk Polytechnic Institute), Novocherkassk,
Rostov-on-Don oblast, Russia
Received March 23, 2010
Abstract—Arylsulfonylation of 1-acetyl-3,5-diamino-1,2,4-triazole with arylsulfonyl chlorides in pyridine, with
the subsequent hydrolysis of the acetyl group, was studied; a new regioselective method for synthesis of N-(5-
amino-1H-1,2,4-triazol-3-yl)arylsulfonamides was developed.
Arylsulfonyl derivatives of 3,5-diamino-1,2,4-
triazole of general formula I are key starting
substances in syntheses of effective herbicides:
N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)- and ([1,2,4]
5]. Some representatives of this group of compounds
exhibit anti-HIV and antitumor activity . Methods for
synthesis of compounds I, described until now, include
construction of an aminotriazole fragment bonded to
the arylsulfamide group by reactions of condensation
of N-(arylsulfonyl)-N’-cyanoimidothiocarbamates with
derivatives of hydrazine [1, 2, 4, 5] or S,S-dimethyl-N-
(arylsulfonyl)carbodithioimidates with aminoguanidine
hydrocarbonates . The main disadvantages of these
methods are the high cost of starting substances and
poor yield of target products .
A promising method for synthesis of compounds
might become arylsulfonylation of 3,5-diamino-1,2,4-
triazole (DAT). However, the high nucleophilicity of the
endocyclic nitrogen, compared with the exocyclic amino
group, results in that this reaction yields 1-arylsulfonyl-
3,5-diamino-1,2,4-triazoles II, rather than compound I
 (Scheme 1).
The goal of our study was to develop a method for
synthesis of compound I from the available 3,5-diamino-
According to published data [8, 9], 1-substituted
3,5-diamino-1,2,4-triazoles are selectively sulfonylated
by arylsulfonyl chlorides at the amino group in position 3