Synthesis 2012(8): 1263-1267  
DOI: 10.1055/s-0031-1290808
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Easy Synthesis of Novel 4-Azolylpyridazin-3-ones

Oleksandr V. Geraschenko*a,b, Pavel V. Khodakovskiya, Oleksandr N. Shivanyukb, Oleg V. Shishkinc, Pavel K. Mykhailiuk*a,b, Andrey A. Tolmacheva,b
a Enamine Ltd., Aleksandra Matrosova Street 23, Kyiv 01103, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Fax: +380(44)2351273; e-Mail: Geraschenko.Aleksandr@gmail.com; e-Mail: Pavel.Mykhailiuk@gmail.com;
c STC, Institute for Single Crystals, National Academy of Science of Ukraine, Lenina Avenue 60, Kharkiv 61001, Ukraine
Further Information

Publication History

Received 1 December 2011
Publication Date:
27 March 2012 (online)

Abstract

Ethyl azol-2-ylglyoxylates react smoothly with acetone in the presence of catalytic amounts of proline and trifluoroacetic acid to give the corresponding azolyl aldols in 93-98% yield. The products are easily transformed into azolyl pyridazinones in 85-98% yield by cyclization with hydrazine hydrate.

    References

  • 1 Conteras JM. Rival YM. Chayer S. Borguignon JJ. Wermuth CG. J. Med. Chem.  1999,  42:  730 
  • 2a Coudert P. Albuisson E. Boire JY. Duroux E. Bastide P. Couquelet J. Eur. J. Med. Chem.  1994,  29:  471 
  • 2b Wermuth C.-G. Schlewer G. Bourguignon J.-J. Maghioros G. Bouchet M.-J. J. Med. Chem.  1989,  32:  528 
  • 2c Máttyus P. Maes BUW. Riedl Z. Hajós G. Lemière GLF. Tapolcsányi P. Monsieurs K. Éliás O. Dommisse RA. Krajsovszky G. Synlett  2004,  1123 ; and references therein
  • 3 Schudt C. Winder S. Müller B. Ukena D. Biochem. Pharmacol.  1991,  42:  153 
  • 4a Isabel E. Powell DA. Black W. Chan C.-C. Crane S. Gordon R. Guay J. Guiral S. Huang Z. Robichaud J. Skorey K. Tawa P. Xu L. Zhang L. Oballa R. Bioorg. Med. Chem. Lett.  2011,  21:  479 
  • 4b Wan Z. Hall A. Jin Y. Xiang J. Yang E. Eatherton A. Smith B. Yang G. Yu H. Wang J. Ye L. Lau L. Yang T. Mitchell W. Cai W. Zhang X. Sang Y. Wang Y. Tong Z. Cheng Z. Hussain I. Elliott J. Matsuoka Y. Bioorg. Med. Chem. Lett.  2011,  21:  4016 
  • 4c Lemoine R. Petersen A. Setti L. Rotstein D. Jekle A. Heilek G. deRosier A. Ji C. Berry P. Rotstein M. Bioorg. Med. Chem. Lett.  2010,  20:  4753 
  • 4d Uto Y. Ueno Y. Kiyotsuka Y. Kurata H. Miyazawa Y. Takagi T. Wakimoto S. Ohsumi J. Eur. J. Med. Chem.  2011,  46:  1892 
  • 5 Laborit H. Agressologie  1969,  10:  469 
  • 6 Worms P. Kan J. Wermuth C. Biziere K. Naunyn-Schmiedeberg’s Arch. Pharmacol.  1986,  334:  246 
  • 7 Mason JW. Aldous DL. In The Chemistry of Heterocyclic Compounds   Vol. 28:  Weissberger A. Taylor EC. Wiley-Interscience; New York: 1973.  p.24 
  • 8 Geraschenko OV. Khodakovskiy P. Shishkin O. Mykhailiuk P. Zaporozhets O. Tolmachev A. Synthesis  2011,  1633 
  • 9a Osamu T. Taichi K. Wei-Guo G. Tetsuya I. Keiji M. Org. Lett.  2005,  7:  22-5103  
  • 9b Nobuyuki M. Fujie T. Carlos F. Angew. Chem. Int. Ed.  2004,  43:  2420 
  • 9c Quan-Zhong L. Xue-Lian W. Shi-Wei L. Bao-Lei Z. Da-Bin Q. Tetrahedron Lett.  2008,  49:  7434 
  • 10 Sibgatulin D. Volochnyuk D. Kostyuk A. Synlett  2005,  1907 
  • 11 SHELXTL, Version 5.10   Bruker AXS Inc.; Madison: 1997.