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

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

References

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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 F^² 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) Å^³, 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.