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

Further Information

Publication History

Received 25 November 2010
Publication Date:
08 March 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

References

1a Chebanov VA. Gura KA. Desenko SM. Top. Heterocycl. Chem. 2010, 23: 41

Google Scholar
1b Chebanov VA. Desenko SM. Gurley TW. Azaheterocycles Based on α,β-Unsaturated Carbonyls Springer; Meppel: 2008.

Google Scholar
2a Chebanov VA. Sakhno YaI. Desenko SM. Shishkina SV. Musatov VI. Shishkin OV. Knyazeva IV. Synthesis 2005, 2597

Google Scholar
2b Chebanov VA. Sakhno YaI. Desenko SM. Chernenko VN. Musatov VI. Shishkina SV. Shishkin OV. Kappe CO. Tetrahedron 2007, 63: 1229

Google Scholar
2c Sakhno YaI. Desenko SM. Shishkina SV. Shishkin OV. Sysoyev DO. Groth U. Kappe CO. Chebanov VA. Tetrahedron 2008, 64: 11041

Google Scholar
2d Sakhno YaI. Shishkina SV. Shishkin OV. Musatov VI. Vashchenko EV. Desenko SM. Chebanov VA. Mol. Diversity 2010, 14: 523

Google Scholar
3a Chebanov VA. Saraev VE. Desenko SM. Chernenko VN. Shishkina SV. Shishkin OV. Kobzar KM. Kappe CO. Org. Lett. 2007, 9: 1691

Google Scholar
3b Chebanov VA. Saraev VE. Desenko SM. Chernenko VN. Knyazeva IV. Groth U. Glasnov TN. Kappe CO. J. Org. Chem. 2008, 73: 5110

Google Scholar
3c Muravyova EA. Shishkina SV. Musatov VI. Shishkin OV. Desenko SM. Chebanov VA. Synthesis 2009, 1375

Google Scholar
4a Lipson VV. Desenko SM. Borodina VV. Shirobokova MG. Musatov VI. Russ. J. Org. Chem. 2005, 41: 114

Google Scholar
4b Chernyshev VM. Sokolov AN. Taranushich VA. Russ. J. Appl. Chem. 2007, 80: 1691

Google Scholar
5a Chernyshev VM. Astakhov AV. Starikova ZA. Tetrahedron 2010, 66: 3301

Google Scholar
5b Chernyshev VM. Rakitov VA. Taranushich VA. Blinov VV. Chem. Heterocycl. Compd. 2005, 41: 1139

Google Scholar
5c Chernyshev VM. Kosov AE. Gladkov ES. Shishkina SV. Taranushich VA. Desenko SM. Shishkin OV. Russ. Chem. Bull., Int. Ed. 2006, 55: 338

Google Scholar
5d Chernyshev VM. Rakitov VA. Taranushich VA. Starikova ZA. Chem. Heterocycl. Compd. 2007, 43: 776

Google Scholar
5e Chernyshev VM. Rakitov VA. Blinov VV. Taranushich VA. Starikova ZA. Chem. Heterocycl. Compd. 2009, 45: 436

Google Scholar
6a Papini P. Gazz. Chim. Ital. 1950, 80: 100

Google Scholar
6b Papini P. Checchi S. Gazz. Chim. Ital. 1950, 80: 850

Google Scholar
6c Papini P. Gazz. Chim. Ital. 1952, 82: 735

Google Scholar
7 Bavley A. inventors; US Patent 2 406 654. ; Chem. Abstr. 1947, 41, 42h
8a Shaban MAE. Morgan AEA. Adv. Heterocycl. Chem. 1999, 73: 131

Google Scholar
8b Golubushina GM. Poshtaruk GN. Chuiguk VA. Chem. Heterocycl. Compd. 1974, 10: 491

Google Scholar
8c Bratulescu G. Synthesis 2005, 2833

Google Scholar
For reviews and related papers on multicomponent reactions see, for example:
9a Multicomponent Reactions Zhu J. Bienayme H. Wiley-VCH; Weinheim: 2005.

Google Scholar
9b Biggs-Houck JE. Younai A. Shaw JT. Curr. Opin. Chem. Biol. 2010, 14: 371

Google Scholar
9c Ganem B. Acc. Chem. Res. 2009, 42: 463

Google Scholar
9d Sunderhaus JD. Martin SF. Chem. Eur. J. 2009, 15: 1300

Google Scholar
9e Isambert N. Lavilla R. Chem. Eur. J. 2008, 14: 8444

Google Scholar
10a Tapia I. Alcazar V. Moran JR. Grande M. Bull. Chem. Soc. Jpn. 1990, 63: 2408

Google Scholar
10b Ghavtadze N. Fröhlich R. Würthwein EU. Eur. J. Org. Chem. 2008, 3656

Google Scholar
10c Abasolo MI. Gaozza CH. Fernandez BM. J. Heterocycl. Chem. 1987, 24: 1771

Google Scholar
10d Liu KC. Shih BJ. Lee CH. J. Heterocycl. Chem. 1992, 29: 97

Google Scholar
10e Groenendaal B. Ruijter E. Orru RVA. Chem. Commun. 2008, 5474

Google Scholar
11 Sheldrick GM. Acta Crystallogr., Sect. A 2008, 64: 112

Crossref PubMed Google Scholar

12

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.