Synthesis 2010(16): 2767-2770  
DOI: 10.1055/s-0030-1258139
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Fused 3-Formylpyridines and 5-Formylpyrimidines

Andrey P. Mityuka, Sergey E. Kolodychb, Sergey A. Mytnykb, Yuri V. Dmytrivb, Dmitriy M. Volochnyuka, Pavel K. Mykhailiuk*a,b, Andrey A. Tolmacheva,b
a Enamine Ltd., Oleksandra Matrosova Street 23, Kiev 01103, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;
b Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, Kiev 01033, Ukraine
Weitere Informationen

Publikationsverlauf

Received 13 April 2010
Publikationsdatum:
01. Juli 2010 (online)

Abstract

Cyclization of 2-dimethylaminomethylene-1,3-bis(di­methylimonio)propane diperchlorate with various amino heterocycles led to the formation of a series of fused heterocyclic systems containing a 3-formylpyridine or 5-formylpyrimidine unit.

    References

  • 1a Yan H. Boehm JC. Jin Q. Kasparec J. Li H. Zhu C. Widdowson KL. Callahan JF. Wan Z. Tetrahedron Lett.  2007,  48:  1205 
  • 1b Bennett LR. Blankley CJ. Fleming RW. Smith RD. Tessman DK. J. Med. Chem.  1981,  24:  382 
  • 1c Angiolini M. Bassini DF. Gude M. Menichincheri M. Tetrahedron Lett.  2005,  46:  8749 
  • 1d Vanlaer S. Compernolle F. Voet A. Gielens C. De Maeyer M. Eur. J. Org. Chem.  2009,  643 
  • 1e Wong A. Kuethe JT. Davies IW. Hughes DL. J. Org. Chem.  2004,  69:  7761 
  • 2a Nishikawa Y. Shindo T. Ishii K. Nakamura H. Kon T. Uno H. J. Med. Chem.  1989,  32:  583 
  • 2b Bleloch A. Johnson BFG. Ley SV. Price AJ. Shephard DS. Thomas AW. Chem. Commun.  1999,  1907 
  • 2c Pham V. Zhang W. Chen V. Whitney T. Yao J. Froese D. Friesen AD. Diakur JM. Haque W. J. Med. Chem.  2003,  46:  3680 
  • 2d VanderWel SN. Harvey PJ. McNamara DJ. Repine JT. Keller PR. Quin J. Booth RJ. Elliott WL. Dobrusin EM. Fry DW. Toogood PL. J. Med. Chem.  2005,  48:  2371 
  • 2e Stuart A. Paterson T. Roth B. Aig E. J. Med. Chem.  1983,  26:  667 
  • 3a Gupton JT. Gall JE. Riesinger SW. Smith SQ. Bevirt KM. Sikorski JA. Dahl ML. Arnold A.
    J. Heterocycl. Chem.  1991,  28:  1281 
  • 3b Ragan JA. McDermott RE. Jones BP. Ende DJ. Clifford PJ. McHardy SJ. Heck SD. Liras S. Segelstein BE. Synlett  2000,  1172 
  • 4 Tom NJ. Ruel EM. Synthesis  2001,  1351 
  • For the reactions of vinamidinium salts 1 and 2, see:
  • 5a Jameleddine K. Adnen HAM. Bechir BH. Tetrahedron Lett.  2006,  47:  2973 
  • 5b Thouraya G. Jameleddine K. Adnen HAM. Bechir BH. Synth. Commun.  2007,  37:  1053 
  • 5c Gupton JT. Krolikowski DA. Yu RH. Riesinger SW. J. Org. Chem.  1990,  55:  4735 
  • 5d Angus RO. Bryce MR. Keshavarz B. Wudl F. Synthesis  1998,  746