Unusual Direction of Cyclocondensation
of 1-(4-Chlorophenyl)-3,5-diamino-1,2,4-triazole, Pyruvic Acid,
and Aldehydes

Yana I. Sakhno; Sergey M. Desenko; Svetlana V. Shishkina; Oleg V. Shishkin; Vladimir I. Musatov; Valentyn A. Chebanov

doi:10.1055/s-0030-1258468

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Synthesis 2011(7): 1120-1124
DOI: 10.1055/s-0030-1258468

PAPER

Unusual Direction of Cyclocondensation of 1-(4-Chlorophenyl)-3,5-diamino-1,2,4-triazole, Pyruvic Acid, and Aldehydes

Yana I. Sakhno^a, Sergey M. Desenko^a,b, Svetlana V. Shishkina^a, Oleg V. Shishkin^a,b, Vladimir I. Musatov^a, Valentyn A. Chebanov*^a
^a SSI ‘Institute for Single Crystals’ NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine
Fax: +38(57)3410273; e-Mail: chebanov@isc.kharkov.com;
^b V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61077, Ukraine

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Publikationsverlauf

Received 25 November 2010
Publikationsdatum:
08. März 2011 (online)

Abstract
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Abstract

The reactivity of 1-(4-chlorophenyl)-3,5-diamino-1,2,4-triazole in multicomponent reactions with pyruvic acid and aldehydes and in two-component reactions with arylidenepyruvic acid was studied. The unusual direction of these treatments leading to the formation of unprecedented 3-[5-amino-1-(4-chlorophenyl)-1,2,4-triazol-3-ylamino]-5-arylfuran-2-ones instead of triazolopyrimidine or triazolylpyrrolone derivatives was found and discussed.

Key words

heterocycles - multicomponent reaction - furans - nucleophiles - regioselectivity

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The final atomic coordinates, and crystallographic data for molecule 11c have been deposited to with the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] and are available on request quoting the deposition number CCDC 793788.