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Synthesis 2008(19): 3088-3098  
DOI: 10.1055/s-2008-1067267
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Some Transformations of Tertiary N-Furfurylamides of Aromatic and Heteroaromatic Carboxylic Acids under Acidic Conditions

Tatyana A. Stroganova*, Vladimir K. Vasilin, Elena A. Zelenskaya, Viktor M. Red’kin, Gennady D. Krapivin
Department of Organic Chemistry, Kuban State University of Technology, Moskovskaya st. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: stroganova@kubstu.ru; e-Mail: tatka_s@mail.ru;
Further Information

Publication History

Received 20 February 2008
Publication Date:
05 September 2008 (online)

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Abstract

Acid-catalyzed transformations of tertiary N-furfuryl­amides of ortho-amino substituted aromatic and heteroaromatic carboxylic acids accompanied by elimination of the furfuryl moiety are investigated.

Key words

N-furfurylamides - elimination - ring opening - pyrrolo[1,2-a]diazepines

    References

  • For reviews, see:
  • 1a Butin AV. Stroganova TA. Abaev VT. Gutnov AV. Targets in Heterocyclic Systems: Chemistry and Properties   Vol. 5:  Attanasi OA. Spinelli D. Italian Society of Chemistry; Rome: 2001.  p.131 
    Google Scholar
  • 1b Piancatelli G. D’Auria M. D’Onofrio F. Synthesis  1994,  867 
    Google Scholar
  • 1c Dean FM. Adv. Heterocycl. Chem.  1982,  31:  237 
    Google Scholar
  • 1d Dean FM. Adv. Heterocycl. Chem.  1982,  30:  167 
    Google Scholar
  • 2a Butin AV. Stroganova TA. Lodina IV. Krapivin GD. Tetrahedron Lett.  2001,  42:  2031 
    Google Scholar
  • 2b Butin AV. Smirnov SK. Stroganova TA. J. Heterocycl. Chem.  2006,  43:  623 
    Google Scholar
  • 2c Butin AV. Smirnov SK. Stroganova TA. Bender W. Krapivin GD. Tetrahedron  2007,  63:  474 
    Google Scholar
  • 3 Stroganova TA. Butin AV. Vasilin VK. Nevolina TA. Krapivin GD. Synlett  2007,  1106 
    Article in Thieme ConnectGoogle Scholar
  • 4 Lin JH, Ramjit HG, Pitzenberger SM, and Ulm EH. inventors; US  4939139.  ; Chem. Abstr. 1990, 113, 191344
  • 5 Hara T, Shikayama Y, Ito K, Mori T, Fujimori H, Sunami T, Hashimoto Y, and Ishimoto Y. inventors; JP  61001433.  ; Chem. Abstr. 1986, 104, 186459
  • 6a Freidinger RM, Evans BE, and Bock MG. inventors; EP  523846.  ; Chem. Abstr. 1993, 119, 8838
  • 6b Freidinger RM, Bock MG, and Evans BE. inventors; EP  272866.  ; Chem. Abstr. 1989, 110, 23918
  • 6c Rajagopalan P. inventors; US  4438120.  ; Chem. Abstr. 1984, 101, 7218
  • 6d Corelli F. Massa S. Pantaleoni GC. Palumbo G. Fanini D. Farmaco, Ed. Sci.  1984,  39:  707 
    Google Scholar
  • 7 Saito Sh, Umemiya H, Suga Y, Sato M, and Kawashima N. inventors; WO  2003095427.  ; Chem. Abstr. 2003, 139, 395821
  • 8 Ivashchenko AV, Vvedensky VY, Ilyn AP, Kysel VM, Khvat AV, Kuzovkova YuA, Kutepov SA, Dmitrieva IG, Zolotarev DA, Tkachenko SY, Okun IM, Kravchenko DV, Kobak VV, Trifilenkov AS, Mishunina YuS, Loseva MV, Rizhova EA, Parchinsky VZ, Tsirulnikov SA, and Kyselev AS. inventors; WO  2005105805.  ; Chem. Abstr. 2005, 143, 452852
  • 9 Meerpoel L. Van Gestel J. Van Gerven F. Woestenborghs F. Marichal P. Sipido V. Gilkerson T. Nash R. Corens D. Richards RD. Bioorg. Med. Chem. Lett.  2005,  15:  3453 
    CrossrefPubMedGoogle Scholar
  • 10 Kaigorodova EA. Konyushkin LD. Mikhailichenko SN. Vasilin VK. Kul’nevich VG. Chem. Heterocycl. Compd. (Engl. Transl.)  1996,  32:  1234 ; Khim. Geterotsikl. Soedin. 1996, 1432
    CrossrefGoogle Scholar
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CCDC 690595 for 9f contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.