Synthesis 2005(15): 2597-2601  
DOI: 10.1055/s-2005-872073
PAPER
© Georg Thieme Verlag Stuttgart · New York

Three-Component Procedure for the Synthesis of 5-Aryl-5,8-dihydroazolo[1,5-a]pyrimidine-7-carboxylic Acids

Valentin A. Chebanov*, Yana I. Sakhno, Sergey M. Desenko, Svetlana V. Shishkina, Vladimir I. Musatov, Oleg V. Shishkin, Irina V. Knyazeva
Department of Photoactive Heterocyclic Compounds, State Scientific Institution ‘Institute for Single Crystals’, Institute for Scintillation Materials of National Academy of Sciences of Ukraine, Lenin Ave 60, Kharkiv 61001 Ukraine
Fax: +38(572)3409343; e-Mail: chebanov@isc.kharkov.com;
Further Information

Publication History

Received 14 March 2005
Publication Date:
18 July 2005 (eFirst)

Abstract

Three-component condensation of pyruvic acid with aromatic aldehydes and some aminoazoles was developed as a procedure for the synthesis 5-aryl-5,8-dihydroazolo[1,5-a]pyrimidine-7-carboxylic acids. An influence of solvent type on the composition of the reaction products was found. The structures of the compounds obtained were proved by 1H and 13C NMR spectroscopy, NOE experiments, and X-ray analysis.

    References

  • 1a Doemling A. Ugi I. Angew. Chem. Int. Ed.  2000,  29:  3168 ; Angew. Chem. 2000, 112, 3300
  • 1b Orru RVA. Greef M. Synthesis  2003,  1471 
  • See, for example:
  • 2a Nosek E. Collect. Czech. Chem. Commun.  1950,  15:  335 
  • 2b Mueller R. J. Prakt. Chem.  1959,  132 
  • 2c Armand J. Armand Y. Boulares L. Bellec C. Pinson J. J. Heterocycl. Chem.  1985,  22:  1519 
  • 2d Kruglenko VP. Klyuev NA. Povstyanoi MV. Timoshin AA. Chem. Heterocycl. Compd.  1998,  34:  232 
  • 2e Berezina ES. Koz’minykh VO. Igidov NM. Shirinkina SS. Koz’minykh EN. Makhmudov RR. Bukanova EV. Russ. J. Org. Chem.  2001,  37:  539 
  • 2f Kistanova NS. Mashevskaya IV. Bozdyreva KS. Maslivets AN. Chem. Heterocycl. Compd.  2003,  39:  673 
  • 3a Abdel-Haby SAL. Badawy MA. Kadry AM. Mosselhi MAN. J. Heterocycl. Chem.  1987,  24:  1587 
  • 3b Abdel-Megid M. Pharmazie  2000,  55:  263 
  • 3c El-Maati TMA. Boll. Chim. Farm.  1999,  138:  272 
  • 3d Chebanov VA. Desenko SM. Sakhno YI. Panchenko ES. Saraev VE. Musatov VI. Konev VF. Physiol. Active Compd.  2002,  33:  10 
  • 4a Epling GA. Provatas AA. Chem. Commun.  2002,  10:  1036 
  • 4b Garzarolli-Thurnlackh K. Monatsh. Chem.  1899,  20:  487 
  • 4c Jablonski W. Ber. Dtsch. Chem. Ges.  1900,  33:  2925 
  • 5 Borsche W. Ber. Dtsch. Chem. Ges.  1908,  41:  3886 
  • 6a Desenko SM. Chem. Heterocycl. Compd.  1995,  31:  125 
  • 6b Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; PCT Int. Patent  8504172.  1985; Chem. Abstr. 1986, 104, 207298
  • 6c Mishina T, Tsuda Y, Inui J, and Mura Y. inventors; Jpn Patent  62169793.  1987; Chem. Abstr. 1988, 108, 56120
  • 6d Tsuda Y, Mishina T, Obata M, and Inui J. inventors; Jpn. Patent  61263977.  1986; Chem. Abstr. 1987, 106, 119901
  • 7a Desenko SM. Orlov VD. Lipson VV. Shishkin OV. Lindeman SV. Struchkov YT. Khim. Geterotsikl. Soedin.  1991,  11:  1539 
  • 7b Desenko SM. Orlov VD. Getmanskii NV. Komykhov SA. Paponov BV. Kovalevsky AY. Shishkin OV. Struchkov YT. Khim. Geterotsikl. Soedin.  1996,  2:  240 
  • 7c Haj MA. Salas JM. Quiros M. Molina J. Faure R. J. Mol. Struct.  2000,  519:  165 
  • 7d Shishkin OV. Getmanskii NV. Desenko SM. Orlov VD. Lindeman SV. Struchkov YT. Russ. Chem. Bull.  1993,  42:  1912 
  • 7e Desenko SM. Orlov VD. Shishkin OV. Barykin KE. Lindeman SV. Struchkov YT. Khim. Geterotsikl. Soedin.  1993,  10:  1357 
  • 8 Zefirov NS. Palyulin VA. Dashevskaya EE. J. Phys. Org. Chem.  1990,  3:  147 
  • 9 Burgi H.-B. Dunitz JD. Structure Correlation   Vol. 2:  VCH; Weinheim: 1994.  p.741 
  • 10 Zefirov YV. Zorkii PM. Usp. Khim.  1989,  58:  713 
  • 11 Sheldrick GM. SHELXTL PLUS, PC Version: A System of Computer Programs for the Determination of Crystal Structure from X-Ray Diffraction Data   Rev.5.1:  University of Göttingen; Germany: 1998.