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Synthesis 2011(11): 1799-1813  
DOI: 10.1055/s-0030-1260026
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Method for the Synthesis of 1-Aryl-1,2,4-triazole Derivatives

Vasyl S. Matiychuka, Mykhaylo A. Potopnyka, Roman Luboradzkib, Mykola D. Obushak*a
a Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, 79005 Lviv, Ukraine
b Institute of Physical Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +38(32)2971668; e-Mail: obushak@in.lviv.ua;
Further Information

Publication History

Received 6 February 2011
Publication Date:
05 May 2011 (online)

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Abstract

A new and convenient one-step recyclization method for the synthesis of ethyl 1-aryl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylates is reported. Various ethyl chloro(2-arylhydrazinylidene)ethanoates react with thiazolidine-2,4-dione in the presence of potassium hydroxide to produce the 1-aryl-1,2,4-triazole derivatives in moderate to good yields. The procedure is economical, environmentally friendly and simple to perform.

Key words

1,2,4-triazoles - diazonium salts - ring-opening - thiazolidine-2,4-dione - heterocyclization

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19

A colorless crystal of approximate dimensions 1.0 × 0.05 × 0.05 mm was used. Diffraction data were collected at 100 K using a Bruker Kappa CCD diffractometer with graphite monochromated MoKα radiation (0.71073 Å). Lorentz-polarization correction was employed, but not for absorptions. The structure was solved by direct methods (SHELXS-97)²¹ and refined on F² using the full-matrix least-squares method (SHELXL-97).²¹ Formula: C11H10ClN3O3, orthorhombic, space group = P212121, a = 4.3850 (2), b = 10.5690 (7), c = 24.8990 (16) Å, V = 1153.95 (12) ų, R 1 = 0.0804 [I>2σ(I)], wR 2 = 0.2070 for all data. The hydrogen atoms were added geometrically and refined with the riding model. The crystallographic data for compound 5f have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 804995. These data can be obtained free of charge via www.ccdc.cam.ac.uk, or on application to the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.