Download PDF
Synthesis 2011(21): 3547-3551  
DOI: 10.1055/s-0030-1260204
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Furan Ring Opening-Pyrrole Ring Closure: A New Route to Pyrrolo[1,2-d][1,4]benzodiazepin-6-ones

Tatyana A. Nevolinaa, Vitaly A. Shcherbinina, Olga V. Serdyukb, Alexander V. Butin*a
a Research Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: alexander_butin@mail.ru; e-Mail: av_butin@yahoo.com;
b Department of Chemistry, Southern Federal University, Zorge 7, Rostov-on-Don 344090, Russian Federation
Further Information

Publication History

Received 18 July 2011
Publication Date:
02 September 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A new method for the synthesis of pyrrolo[1,2-d][1,4]benzodiazepines is described. The method is based on the acid-catalyzed recyclization of N-[2-(5-alkyl-2-furyl)phenyl]-2-aminoacetamides and permits the formation of both diazepine and pyrrole rings in one pot. The reaction proceeds via furan ring opening to give the diketone moiety followed by consecutive reactions of the free amino group with both carbonyl functions.

Key words

furans - ring opening - ring closure - fused-ring system - pyrrolo[1,2-d][1,4]benzodiazepines - Paal-Knorr reaction

    References

  • 1 Leimgruber W. Batcho AD. Czajkowski RC. J. Am. Chem. Soc.  1968,  90:  5641 
    CrossrefSearch in Google Scholar
  • 2 For review, see: Thurston DE. Bose DS. Chem. Rev.  1994,  94:  433 
    CrossrefSearch in Google Scholar
  • For some recent examples, see:
  • 3a Hadjivassileva T. Thurston DE. Taylor PW. J. Antimicrob. Chemother.  2005,  56:  513 
    Search in Google Scholar
  • 3b Masterson LA. Spanswick VJ. Hartley JA. Begent RH. Howard PW. Thurston DE. Bioorg. Med. Chem. Lett.  2006,  16:  252 
    Search in Google Scholar
  • 3c Antonow D. Jenkins TC. Howard PW. Thurston DE. Bioorg. Med. Chem.  2007,  15:  3041 
    Search in Google Scholar
  • 3d Kamal A. Kumar PP. Seshadri BN. Srinivas O. Kumar MS. Sen S. Kurian N. Juvekar AS. Zingde SM. Bioorg. Med. Chem.  2008,  16:  3895 
    Search in Google Scholar
  • 4a Mai A. Di Santo R. Massa S. Artico M. Pantaleoni GC. Giorgi R. Coppolino MF. Barracchini A. Eur. J. Med. Chem.  1995,  30:  593 
    Search in Google Scholar
  • 4b Hara T. Kayama Y. Mori T. Itoh K. Fujimori H. Sunami T. Hashimoto Y. Ishimoto S. J. Med. Chem.  1978,  21:  263 
    Search in Google Scholar
  • 4c Meerpoel L. Van Gestel J. Van Gerven F. Woestenborghs F. Marichal P. Sipido V. Terence G. Nash R. Corens D. Richards RD. Bioorg. Med. Chem. Lett.  2005,  15:  3453 
    Search in Google Scholar
  • 5a Aiello E. Dattolo G. Cirrincione G. Plescia S. Daidone G. J. Heterocycl. Chem.  1979,  16:  209 
    Search in Google Scholar
  • 5b Dattolo G. Cirrincione G. Aiello E. J. Heterocycl. Chem.  1980,  17:  701 
    Search in Google Scholar
  • 5c De Lucca GV. Otto MJ. Bioorg. Med. Chem. Lett.  1992,  2:  1639 
    Search in Google Scholar
  • 6 For review, see: Timoshenko DO. Adv. Heterocycl. Chem.  2008,  96:  1 
    Search in Google Scholar
  • 7 Iden HS. Lubell WD. Org. Lett.  2006,  8:  3425 
    CrossrefSearch in Google Scholar
  • For reviews, see:
  • 8a Dean FM. Adv. Heterocycl. Chem.  1982,  30:  167. 
    Search in Google Scholar
  • 8b Dean FM. Adv. Heterocycl. Chem.  1982,  31:  237 
    Search in Google Scholar
  • 8c Piancatelli G. D’Auria M. D’Onofrio F. Synthesis  1994,  867 
  • 9a Kayama Y. Hara T. Itoh K. Sunami T. J. Heterocycl. Chem.  1977,  14:  171 
    Search in Google Scholar
  • 9b Fujimori H. Kayama Y. Hara T. Itoh K. Sunami T. J. Heterocycl. Chem.  1977,  14:  235 
    Search in Google Scholar
  • 9c Butin AV. Nevolina TA. Shcherbinin VA. Uchuskin MG. Serdyuk OV. Trushkov IV. Synthesis  2010,  2969 
  • 10a Stroganova TA. Butin AV. Vasilin VK. Nevolina TA. Krapivin GD. Synlett  2007,  1106 
  • 10b Butin AV. Nevolina TA. Shcherbinin VA. Trushkov IV. Cheshkov DA. Krapivin GD. Org. Biomol. Chem.  2010,  8:  3316 
    Search in Google Scholar
  • 11 Butin AV. Tsiunchik FA. Abaev VT. Zavodnik VE. Synlett  2008,  1145 
    Thieme Connect