Download PDF
Synthesis 2012(2): 201-206  
DOI: 10.1055/s-0031-1289633
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile One-Pot Synthesis of Substituted Thieno[2,3-b]pyridines from Enaminones

Baochang Gaoa,b, Dewen Dongb, Jie Zhanga, Changjiang Ding*a, Chunming Dongb, Yongjiu Liangb, Rui Zhang*b
a Department of Chemistry, Jilin University, Changchun 130012, P. R. of China
Fax: +86(431)85262676; e-Mail: ariel@ciac.jl.cn; e-Mail: dcjiang@163.com;
b Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. of China
Further Information

Publication History

Received 7 September 2011
Publication Date:
05 December 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A facile and efficient one-pot synthesis of substituted thieno[2,3-b]pyridines has been developed. Treatment of enamin­ones, such as 2-acetyl-3-(dimethylamino)propenamides and -propenoates, with 2-cyanothioacetamide in the presence of potassium carbonate in N,N-dimethylformamide at 80 ˚C followed by addition of methylene-active bromides at room temperature provided, via intramolecular cyclization, 2,3,5,6-tetrasubstituted thieno[2,3-b]pyridines in yields of 78-90%. This protocol, which combines construction and modification of the thieno[2,3-b]pyridine ring, increases the structural diversity of the final products from readily available materials.

Key words

enaminones - cyclization - heterocycles - pyridine-2(1H)-thiones - thieno[2,3-b]pyridines

    References

  • 1a Gibson VC. Redshaw C. Solan GA. Chem. Rev.  2007,  107:  1745 
    Google Scholar
  • 1b Ma XQ. Gang DR. Nat. Prod. Rep.  2004,  21:  752 
    Google Scholar
  • 1c Vidaillac C. Guillon J. Arpin C. Forfar-Bares I. Ba BB. Grellet J. Moreau S. Caignard DH. Jarry C. Quentin C. Antimicrob. Agents Chemother.  2007,  51:  831 
    Google Scholar
  • 2a Temple C. Rener GA. Waud WR. Noker PE. J. Med. Chem.  1992,  35:  3686 
    Google Scholar
  • 2b Mahata PK. Venkatesh C. Kumar UKS. Ila H. Junjappa H. J. Org. Chem.  2003,  68:  3966 
    Google Scholar
  • 3 Balasubramanian M. Keay JG. In Comprehensive Heterocyclic Chemistry II   Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.245-300  
    Google Scholar
  • 4a Schnute ME. Anderson DJ. Brideau RJ. Ciske FL. Collier SA. Cudahy MM. Eggen M. Genin MJ. Hopkins TA. Judge TM. Kim EJ. Knechtel ML. Nair SK. Nieman JA. Oien NL. Scott A. Tanis SP. Vaillancourt VA. Wathen MW. Wieber JL. Bioorg. Med. Chem. Lett.  2007,  17:  3349 
    Google Scholar
  • 4b Schnute ME. Cudahy MM. Brideau RJ. Homa FL. Hopkins TA. Knechtel ML. Oien NL. Pitts TW. Poorman RA. Wathen MW. Wieber JL. J. Med. Chem.  2005,  48:  5794 
    Google Scholar
  • 5 Bahekar RH. Jain MR. Jadav PA. Prajapati VM. Patel DN. Gupta AA. Sharma A. Tom R. Bandyopadhya D. Modi H. Patel PR. Bioorg. Med. Chem.  2007,  15:  6782 
    Google Scholar
  • 6a Abdel-Rahman AE. Bakhite EA. Al-Taifi EA. Pharmazie  2003,  58:  372 
    Google Scholar
  • 6b Eldin SM. Z. Naturforsch., B: Chem. Sci.  1999,  54b:  674 
    Google Scholar
  • 6c Hussin AM. Abu-Shanab FA. Ishak EA. Phosphorus, Sulfur Silicon Relat. Elem.  2000,  159:  55 
    Google Scholar
  • 7 Hayakawa I. Shioya R. Agatsuma T. Furukawa H. Sugano Y. Bioorg. Med. Chem. Lett.  2004,  14:  3411 
    Google Scholar
  • 8 Bernardino AMR. Pinheiro LC. da S.. Rodrigues CR. Loureiro NI. Castro HC. Lanfredi-Rangel A. Sabtini-Lopes J. Borges JC. Carvalho JM. Romeiro GA. Ferreira VF. Fruguphetti ICPP. Vannier-Santos MA. Bioorg. Med. Chem.  2006,  14:  5765 
    Google Scholar
  • 9 Krauze A. Germame S. Eberlins O. Sturms I. Klusa V. Duburs G. Eur. J. Med. Chem.  1999,  34:  301 
    Google Scholar
  • 10a Buchstaller HP. Siebert CD. Steinmetz R. Frank I. Berger ML. Gottschlich R. Leibrock J. Krug M. Steinhilber D. Noe CR. J. Med. Chem.  2006,  49:  864 
    Google Scholar
  • 10b May BCH. Zorn JA. Witkop J. Sherrill J. Wallace AC. Legname G. Prusiner SB. Cohen FE. J. Med. Chem.  2007,  50:  65 
    Google Scholar
  • 11 Suarez M. Ochoa E. Pita B. Espinosa R. Gonzalez L. Martin N. Quinteiro M. Seoane C. Soto JL. J. Heterocycl. Chem.  1997,  34:  931 
    Google Scholar
  • 12a Elneairy MAA. Gad-Elkareem MAM. Abdel-Fattah AM. Phosphorus, Sulfur Silicon Relat. Elem.  2006,  181:  1451 
    Google Scholar
  • 12b Abdelhamid AO. Ismail ZH. Abdel-Gawad SM. Ghorab MM. Abdel-Aziem A. Phosphorus, Sulfur Silicon Relat. Elem.  2009,  184:  58 
    Google Scholar
  • 12c Aitken RA. Garnett AN. New J. Chem.  2009,  33:  2402 
    Google Scholar
  • 13 Song YH. Seo JM. J. Heterocycl. Chem.  2007,  44:  1439 
    Google Scholar
  • 14a Gad-Elkareem MAM. Elneairy MAA. Taha AM. Heteroat. Chem.  2007,  18:  405 
    Google Scholar
  • 14b Song YH. Seo JM. J. Heterocycl. Chem.  2007,  44:  1439 
    Google Scholar
  • 14c Abu-Shanab FA. Elkholy YM. Elnagdi MH. Synth. Commun.  2002,  32:  3493 
    Google Scholar
  • 15 Zhang R. Zhang DY. Guo YL. Zhou GY. Jiang ZJ. Dong DW. J. Org. Chem.  2008,  73:  9504 
    Google Scholar
  • 16 Xiang D. Yang Y. Zhang R. Liang Y. Pan W. Huang J. Dong D. J. Org. Chem.  2007,  72:  8593 
    Google Scholar
  • 17 Zhang R. Zhang D. Liang Y. Zhou G. Dong D. J. Org. Chem.  2011,  76:  2880 
    Google Scholar
  • 18 Zhang R. Liang YJ. Zhou GY. Wang KW. Dong DW. J. Org. Chem.  2008,  73:  8089 
    Google Scholar
  • 19 Huang J. Liang Y. Pan W. Yang Y. Dong D. Org. Lett.  2007,  9:  5345 
    Google Scholar
  • 21a El-Saghier A. Molecules  2002,  7:  756 
    Google Scholar
  • 21b Mohareb RM. Shams HZ. Elkholy YM. Azam RA. Phosphorus, Sulfur Silicon Relat. Elem.  1999,  155:  215 
    Google Scholar
  • 21 Yakunin YY. Dyachenko VD. Litvinov VP. Chem. Heterocycl. Compd. (Engl. Transl.)  2001,  37:  581 
    Google Scholar