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Synthesis 2011(16): 2629-2638  
DOI: 10.1055/s-0030-1260118
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Furan Ring Opening - Pyridine Ring Closure: New Route to Quinolines under the Bischler-Napieralski Reaction Conditions

Alexander V. Butin*a, Fatima A. Tsiunchika, Olga N. Kostyukovaa, Maxim G. Uchuskina, Igor V. Trushkovb,c
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, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation
c Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology, Leninskii av. 117/2, Moscow 117997, Russian Federation
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Publication History

Received 18 April 2011
Publication Date:
14 July 2011 (online)

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Abstract

A new approach to highly functionalized quinolines is proposed. This approach is based on the electrophilic recyclization of 2-[2-(acylamino)benzyl]furans under the Bischler-Napieralski reaction conditions.

Key words

furans - ring opening - ring closure - fused-ring systems - quinolines - Bischler-Napieralski reaction

    References

  • 1a Bischler A. Napieralski B. Ber. Dtsch. Chem. Ges.  1893,  26:  1903 
    Google Scholar
  • 1b Whaley WM. Govindachari TR. Org. React.  1951,  6:  74 
    Google Scholar
  • 1c Fodor G. Nagubandi S. Tetrahedron  1980,  36:  1279 
    Google Scholar
  • 1d Love BE. Org. Prep. Proced. Int.  1996,  28:  1 
    Google Scholar
  • 1e Chrzanowska M. Rozwadowska MD. Chem. Rev.  2004,  104:  3341 
    Google Scholar
  • For recent examples, see:
  • 2a Zein AL. Dakhil OO. Dawe LN. Georghiou PE. Tetrahedron Lett.  2010,  51:  177 
    Google Scholar
  • 2b LeGendre O. Pecic S. Chaudhary S. Zimmerman SM. Fantegrossi WE. Harding WW. Bioorg. Med. Chem. Lett.  2010,  20:  628 
    Google Scholar
  • 2c Sobarzo-Sanchez E. Uriarte E. Santana L. Tapia RA. Lourido PP. Helv. Chim. Acta  2010,  93:  1385 
    Google Scholar
  • 2d Kölzer M. Weitzel K. Göringer HU. Thines E. Opatz T. ChemMedChem  2010,  5:  1456 
    Google Scholar
  • 2e Jadhav VB. Nayak SK. Guru Row TN. Kulkami MV. Eur. J. Med. Chem.  2010,  45:  3575 
    Google Scholar
  • 2f Awuah E. Capretta A. J. Org. Chem.  2010,  75:  5627 
    Google Scholar
  • 2g Caille F. Buron F. Toth E. Suzenet F. Eur. J. Org. Chem.  2011,  2120 
    Google Scholar
  • For recent examples, see:
  • 3a Lee C.-S. Liu C.-K. Chiang YL. Cheng Y.-Y. Tetrahedron Lett.  2008,  49:  481 
    Google Scholar
  • 3b Czarnocki SJ. Wojtaciewicz K. Jozwiak AP. Maurin JK. Czarnocki Z. Drabowicz J. Tetrahedron  2008,  64:  3176 
    Google Scholar
  • 3c da Silva WA. Rodrigues MT. Shankaraiah N. Ferreira RB. Andrade CKZ. Pilli RA. Santos LS. Org. Lett.  2009,  11:  3238 
    Google Scholar
  • 3d Takahashi Y. Ishiyama H. Kubota T. Kobayashi J. Bioorg. Med. Chem. Lett.  2010,  20:  4100 
    Google Scholar
  • 3e Brahmbhatt KG. Ahmed N. Sabde S. Mitra D. Singh IP. Bhutani KK. Bioorg. Med. Chem. Lett.  2010,  20:  4416 
    Google Scholar
  • 4a Ohkubo M. Kuno A. Katsuta K. Ueda Y. Shirakawa K. Nakanishi H. Kinoshita T. Takasugi H. Chem. Pharm. Bull.  1996,  44:  778 
    Google Scholar
  • 4b Liu J. Diwu Z. Leung W.-Y. Lu Y. Patch B. Haugland RP. Tetrahedron Lett.  2003,  44:  4355 
    Google Scholar
  • 5 Clarke K. Hughes CG. Humphries AJ. Scrowston RM. J. Chem. Soc. C  1970,  1013 
    Google Scholar
  • 6 Guillon J. Forfar I. Mamani-Matsuda M. Desplat V. Saliege M. Thiolat D. Massip S. Tabourier A. Leger J.-M. Dufaure B. Haumont G. Jarry C. Mossalayi D. Bioorg. Med. Chem.  2007,  15:  194 
    CrossrefPubMedGoogle Scholar
  • 7 Zheng W. Nikulin VI. Konkar AA. Vansal SS. Shams G. Feller DR. Miller DD. J. Med. Chem.  1999,  42:  2287 
    CrossrefGoogle Scholar
  • 8a Besselievre R. Husson H.-P. Tetrahedron  1981,  37:  241 
    Google Scholar
  • 8b Maftouh M. Besselievre R. Monsarrat B. Lesca P. Meunier B. Husson HP. Paoletti C. J. Med. Chem.  1985,  28:  708 
    Google Scholar
  • 8c Bäckvall J.-E. Plobeck NA. J. Org. Chem.  1990,  55:  4528 
    Google Scholar
  • 9a Clark MT. Chang J. Navran SS. Akbar H. Mukhopadhyay A. Amin H. Feller DR. Miller DD. J. Med. Chem.  1986,  29:  181 
    Google Scholar
  • 9b Enzensperger C. Lehmann J. J. Med. Chem.  2006,  49:  6408 
    Google Scholar
  • 9c Enzensperger C. Müller FKU. Schmalwasser B. Wiecha P. Traber H. Lehmann J. J. Med. Chem.  2007,  50:  4528 
    Google Scholar
  • 10a Andres JI. Alcazar J. Alonso JM. Diaz A. Fernandez J. Gil P. Iturrino L. Matesanz E. Meert TF. Megens A. Sipido VK. Bioorg. Med. Chem. Lett.  2002,  12:  243 
    Google Scholar
  • 10b Pawlowska J. Czarnocki Z. Wojtaciewicz K. Maurin JK. Tetrahedron: Asymmetry  2003,  14:  3335 
    Google Scholar
  • 11a Wardrop AWH. Sainsbury GL. Harrison JM. Inch TD. J. Chem. Soc., Perkin Trans. 1  1976,  1279 
    Google Scholar
  • 11b Heaney H. Shuhaibar KF. Tetrahedron Lett.  1994,  35:  2751 
    Google Scholar
  • 12 Umemiya H. Fukasawa H. Ebisawa M. Eyrolles L. Kawachi E. Eisenmann G. Gronemeyer H. Hashimoto Y. Shudo K. Kagechika H. J. Med. Chem.  1997,  40:  4222 
    CrossrefGoogle Scholar
  • 13a Cairns J. Clarkson TR. Hamersma JAM. Rae DR. Tetrahedron Lett.  2002,  43:  1583 
    Google Scholar
  • 13b Cobo J. Nogueras M. Low JN. Rodriguez R. Tetrahedron Lett.  2008,  49:  7271 
    Google Scholar
  • 14a Fu R. Xu X. Dang Q. Bai X. J. Org. Chem.  2005,  70:  10810 
    Google Scholar
  • 14b Xu X. Guo S. Dang Q. Chen J. Bai X. J. Comb. Chem.  2007,  9:  773 
    Google Scholar
  • 15 Hunziker F. Fischer R. Kipfer P. Schmutz J. Bürki HR. Eichenberger E. White TG. Eur. J. Med. Chem.  1981,  16:  391 
    Google Scholar
  • 16a Herz W. Tocker S. J. Am. Chem. Soc.  1955,  77:  3554 
    Google Scholar
  • 16b Sano T. Toda J. Shoda M. Yamamoto R. Ando H. Isobe K. Hosoi S. Tsuda Y. Chem. Pharm. Bull.  1992,  40:  3145 
    Google Scholar
  • 17 Ogawa M. Koyanagi J. Sakuma K. Tanaka A. Yamamoto K. J. Heterocycl. Chem.  1999,  36:  819 
    CrossrefGoogle Scholar
  • 18 Butin AV. Tsiunchik FA. Kostyukova ON. Trushkov IV. Khim. Geterotsikl. Soedin.  2010,  1900 
    Google Scholar
  • 19 Butin AV. Smirnov SK. Stroganova TA. Bender W. Krapivin GD. Tetrahedron  2007,  63:  474 
    CrossrefGoogle Scholar
  • 20 Fitzpatrick JE. Milner DJ. White P. Synth. Commun.  1982,  12:  489 
    CrossrefGoogle Scholar
  • 21 Butin AV. Smirnov SK. Tsiunchik FA. Uchuskin MG. Trushkov IV. Synthesis  2008,  2943 
    Article in Thieme ConnectGoogle Scholar
  • 23a Doi S. Shirai N. Sato Y. J. Chem. Soc., Perkin Trans. 1  1997,  2217 
    Google Scholar
  • 23b Ishikawa T. Shimooka K. Narioka T. Noguchi S. Saito T. Ishikawa A. Yamazaki E. Harayama T. Seki H. Yamaguchi K. J. Org. Chem.  2000,  65:  9143 
    Google Scholar
  • 24a Abaev VT. Gutnov AV. Butin AV. Zavodnik VE. Tetrahedron  2000,  56:  8933 
    Google Scholar
  • 24b Hashmi ASK. Frost TM. Bats JW. J. Am. Chem. Soc.  2000,  122:  11553 
    Google Scholar
  • 24c Yamamura K. Kawabata S. Kimura T. Eda K. Hashimoto M. J. Org. Chem.  2005,  70:  8902 
    Google Scholar
  • 24d Tokumaru K. Arai S. Nishida A. Org. Lett.  2006,  8:  27 
    Google Scholar
  • 24e Ueda I. Nishiura M. Takahashi T. Eda K. Hashimoto M. Yamamura K. Tetrahedron Lett.  2006,  47:  8535 
    Google Scholar
  • 24f Abaev VT. Tsiunchik FA. Gutnov AV. Butin AV. J. Heterocycl. Chem.  2008,  45:  475 
    Google Scholar
  • 24g Butin AV. Tsiunchik FA. Abaev VT. Zavodnik VE. Synlett  2008,  1145 
    Google Scholar
  • 24h Chen Y. Lu Y. Li G. Liu Y. Org. Lett.  2009,  11:  3838 
    Google Scholar
  • 24i Butin AV. Uchuskin MG. Pilipenko AS. Tsiunchik FA. Cheshkov DA. Trushkov IV. Eur. J. Org. Chem.  2010,  920 
    Google Scholar
  • 24j El Kaïm L. Grimaud L. Wagschal S. Chem. Commun.  2011,  47:  1887 
    Google Scholar
  • 25a Butin AV. Smirnov SK. Stroganova TA. J. Heterocycl. Chem.  2006,  43:  623 
    Google Scholar
  • 25b Abaev VT. Dmitriev AS. Gutnov AV. Podelyakin SA. Butin AV. J. Heterocycl. Chem.  2006,  43:  1195 
    Google Scholar
  • 25c Dmitriev AS. Abaev VT. Bender W. Butin AV. Tetrahedron  2007,  63:  9437 
    Google Scholar
  • 25d Butin AV. Abaev VT. Mel’chin VV. Dmitriev AS. Pilipenko AS. Shashkov AS. Synthesis  2008,  1798 
    Google Scholar
  • 26 For a review dealing with methods for the synthesis of quinolines, see: Kouznetsov VV. Mendez LYV. Comez CMM. Curr. Org. Chem.  2005,  9:  141 
    CrossrefGoogle Scholar
  • 27 Butin AV. Kostyukova ON. Tsiunchik FA. Uchuskin MG. Serdyuk OV. Trushkov IV. J. Heterocycl. Chem.  2011,  48:  684 
    CrossrefGoogle Scholar
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CCDC 820334 (for 3a) contains the supplementary crystallographic data for this paper. Copies of the data can be obtained, free of charge, on application to the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.