Regioselective Reaction of Ethyl
5-Acetyl-3,4-dihydropyridine-1(2H)-carboxylate
with Hydrazines: A Facile Approach to New Pyrazole Derivatives

Nazar B. Maximov; Pavel K. Mykhailiuk; Sergey M. Golovach; Anton V. Tverdokhlebov; Zoya V. Voitenko; Andrey A. Tolmachev

doi:10.1055/s-0029-1219760

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(11): 1781-1792
DOI: 10.1055/s-0029-1219760

PAPER

Regioselective Reaction of Ethyl 5-Acetyl-3,4-dihydropyridine-1(2H)-carboxylate with Hydrazines: A Facile Approach to New Pyrazole Derivatives

Nazar B. Maximov^a,b, Pavel K. Mykhailiuk*^a,b, Sergey M. Golovach^a, Anton V. Tverdokhlebov^a,b, Zoya V. Voitenko^b, Andrey A. Tolmachev^a,b
^a Enamine Ltd., Alexandra Matrosova Street 23, Kiev 01103, Ukraine
^b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, Kiev 01033, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;

Further Information

Publication History

Received 26 February 2010
Publication Date:
06 April 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The reaction of ethyl 5-acetyl-3,4-dihydropyridine-1(2H)-carboxylate with diverse aliphatic as well as aromatic monosubstituted hydrazines resulted in the regioselective formation of N-substituted 3-methylpyrazoles.

Key words

pyrazole - hydrazine - tetrahydropyridine - regioselectivity

References

1 Elguero J. Goya P. Jagerovic N. Silva AMS. Targets Heterocycl. Syst. 2002, 6: 52 ; and references therein

Google Scholar
2a Singer RA. Caron S. McDermott RE. Arpin P. Do NM. Synthesis 2003, 1727

Google Scholar
2b Singer RA. Dore M. Sieser JE. Berliner MA. Tetrahedron Lett. 2006, 47: 3727

Google Scholar
3a Quin LD. Pinion DO. J. Org. Chem. 1970, 35: 3134

Google Scholar
3b Bajnati A. Huber-Habart M. Bull. Soc. Chim. Fr. 1988, 3: 540

Google Scholar
3c Quan PM. Quin LD. J. Org. Chem. 1966, 31: 2487

Google Scholar
3d Wenkert E. Moeller P. Pietre S. J. Am. Chem. Soc. 1988, 110: 7188

Google Scholar
3e Wenkert E. Hudlicky T. J. Org. Chem. 1968, 33: 747

Google Scholar
3f Quin LD. Pinion DO. J. Org. Chem. 1970, 35: 3130

Google Scholar
3g Wenkert E. Dave K. Haglid F. Lewis R. Oishi T. Stevens R. Terashima M. J. Org. Chem. 1968, 33: 747

Google Scholar
3h Lei A. Chan M. He M. Zhang X. Eur. J. Org. Chem. 2006, 19: 4343

Google Scholar
4a Okada E. Heterocycles 1992, 34: 791

Google Scholar
4b Menozzi G. Mosti L. Schenone P. J. Heterocycl. Chem. 1987, 24: 1669

Google Scholar
4c Dehayes C. Chabannet M. Gelin S. Synthesis 1982, 1088

Google Scholar
4d Dehayes C. Chabannet M. Gelin S. J. Heterocycl. Chem. 1984, 21: 301

Google Scholar
4e Golovinsky EV. Spassova MK. Zakharieva RD. Z. Chem. 1980, 20: 95

Google Scholar
4f Bajnati A. Bull. Soc. Chim. Fr. 1988, 3: 540

Google Scholar