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Synthesis 2009(14): 2393-2402  
DOI: 10.1055/s-0029-1217396
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Fluorinated Benzofuro- and Benzothieno[2,3-b]pyridines, α-Carbolines and Nucleosides Containing the α-Carboline Framework

Viktor O. Iaroshenko*a,b, Yan Wangc, Biao Zhangc, Dmitriy Volochnyukd, Vyacheslav Ya. Sosnovskikhe
a Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kiev 33, Ukraine
c Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstr. 10, 78457 Konstanz, Germany
d Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev 94, Ukraine
e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
Further Information

Publication History

Received 24 December 2008
Publication Date:
22 June 2009 (online)

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Abstract

Fluorinated benzofuro[2,3-b]pyridines, benzo­thieno[2,3-b]pyridines and 9H-pyrido[2,3-b]indoles (α-carbolines) were synthesized via regiospecific pyridine core annulation of a number of fluoro-containing 1,3-CCC-dielectrophiles to benzofuran-2-amine, benzothiophen-2-amine and 1H-indol-2-amine. Based on the 2,4-bis(trifluoromethyl)-9H-pyrido[2,3-b]indole thus synthesized, the preparative approach towards a set of nucleosides and nucleoside mimetics bearing the α-carboline framework was elaborated.

Key words

pyridines - fluorine - annulation - functionalization - α-carbolines - nucleosides

    References

  • 1a Iaroshenko VO. Volochnyuk DM. Wang Y. Vovk MV. Boiko VJ. Rusanov EB. Groth UM. Tolmachev AA. Synthesis  2007,  3309 
    Google Scholar
  • 1b Volochnyuk DM. Pushechnikov AO. Krotko DG. Sibgatulin DA. Kovalyova SA. Tolmachev AA. Synthesis  2003,  1531 
    Google Scholar
  • 1c Iaroshenko VO. Volochnyuk DM. Kryvokhyzha NV. Martyloga A. Sevenard DV. Groth U. Brand J. Chernega AN. Shivanyuk AN. Tolmachev AA. Synthesis  2008,  2337 
    Google Scholar
  • 1d Iaroshenko VO. Sevenard DV. Kotljarov A. Volochnyuk DM. Tolmachev AO. Sosnovskikh VYa. Synthesis  2009,  731 
    Google Scholar
  • 2 Iaroshenko VO. Groth U. Kryvokhyzha NV. Obeid S. Tolmachev AA. Wesch T. Synlett  2008,  343 
    Article in Thieme ConnectGoogle Scholar
  • 3 Shridhar DR. Reddy Sastry CV. Lal KB. Bansal OP. Sondhi SM. J. Indian Chem. Soc.  1978,  55:  910 
    Google Scholar
  • 4 Sundaram GSM. Venkatesh C. Syam KUK. Ila H. Junjappa H. J. Org. Chem.  2004,  69:  5760 
    Google Scholar
  • 5 Abramov MA. Ceulemans E. Jackers C. Van der Auweraer M. Dehaen W. Tetrahedron  2001,  57:  9123 
    CrossrefGoogle Scholar
  • 6a Simons C. Wu Q. Htar TT. Curr. Top. Med. Chem.  2005,  5:  1191 
    Google Scholar
  • 6b Zapf CW. Bloom JD. Levin JI. Annu. Rep. Med. Chem.  2007,  42:  281 
    Google Scholar
  • 7a Brigden D. Fiddian P. Rosling AE. Ravenscroft T. Antiviral Res.  1981,  1:  203 
    Google Scholar
  • 7b De Clercq E. Naesens L. De Bolle L. Schols D. Zhang Y. Neyts J. Rev. Med. Virol.  2001,  11:  381 
    Google Scholar
  • 7c Abdel-Haq N. Chearskul P. Al-Tatari H. Asmar B. Indian J. Pediatr.  2006,  73:  313 
    Google Scholar
  • 8a Rolfes RJ. Biochem. Soc. Trans.  2006,  34:  786 
    Google Scholar
  • 8b Christopherson RJ. Lyons SD. Wilson PK. Acc. Chem. Res.  2002,  35:  961 
    Google Scholar
  • 8c Manfredi JP. Holmes EW. Ann. Rev. Physiol.  1985,  47:  691 
    Google Scholar
  • 8d Berens RL. Krug EC. Marr JJ. Biochemistry and Molecular Biology of Parasites   Marr JJ. Müller M. Elsevier; Amsterdam: 1995.  p.89 
    Google Scholar
  • 9 Marminon C. Pierre A. Pfeiffer B. Perez V. Leonce S. Renard P. Prudhomme M. Bioorg. Med. Chem.  2003,  11:  679 
    CrossrefPubMedGoogle Scholar
  • 10 Prudhomme M, Marminon C, Routier S, Coudert G, Merour J.-Y, Hickman J, Pierre A, Renard P, and Pfeiffer B. inventors; Int. Patent WO  002563.  ; Chem. Abstr. 2003, 138, 22877
  • 11 Henon H. Messaoudi S. Anizon F. Aboab B. Kucharczyk N. Leonce S. Golsteyn RM. Pfeiffer B. Prudhomme M. Eur. J. Pharmacol.  2007,  554:  106 
    CrossrefPubMedGoogle Scholar
  • 12 Vorbrüggen H. Ruh-Pohlenz C. Handbook of Nucleoside Synthesis   Wiley & Sons; New York: 2001. 
    Google Scholar
  • 13 Hirao I. Mitsui T. Kimoto M. Yokoyama S. J. Am. Chem. Soc.  2007,  129:  15549 
    CrossrefPubMedGoogle Scholar
  • 14a Yang M. Ye W. Schneller SW. J. Org. Chem.  2004,  69:  3993 
    Google Scholar
  • 14b Crimmins MT. Tetrahedron  1998,  54:  9229 
    Google Scholar
  • 15 Kaiwar V. Reese CB. Gray EJ. Neidle S. J. Chem. Soc., Perkin Trans. 1  1995,  2281 
    CrossrefGoogle Scholar
  • 16 Saville-Stones EA. Lindell SD. Jennings NS. Head JC. Ford MJ. J. Chem. Soc., Perkin Trans. 1  1991,  2603 
    CrossrefGoogle Scholar
  • 17 Beauchamp LMB. Serling L. Kelsey JE. Biron K. Collins KP. Selway J. Lin J.-C. Schaeffer HJ. J. Med. Chem.  1988,  31:  144 
    CrossrefGoogle Scholar
  • 18 Hashmi SAN. Hu X. Immoos CE. Lee SJ. Grinstaff MW. Org. Lett.  2002,  4:  4571 
    CrossrefPubMedGoogle Scholar
  • 19 Ludek OR. Meier C. Synthesis  2003,  2101 
    Article in Thieme ConnectGoogle Scholar
  • 20 Kaiwar V. Reese CB. Gray EJ. Neidle S. J. Chem. Soc., Perkin Trans. 1  1995,  2281 
    CrossrefGoogle Scholar
  • 21a Palmer AM. Jager V. Eur. J. Org. Chem.  2001,  1293 
    Google Scholar
  • 21b Paquette LA. Bailey S. J. Org. Chem.  1995,  60:  7849 
    Google Scholar
  • 21c Gallos JK. Koftis TV. Koumbis AE. J. Chem. Soc., Perkin Trans. 1  1994,  611 
    Google Scholar
  • 21d Choi WJ. Park JG. Yoo SJ. Kim HO. Moon HR. Chun MW. Jung YH. Jeong LS. J. Org. Chem.  2001,  66:  6490 
    Google Scholar
  • 21e Jin YH. Wang J. Baker R. Huggins J. Chu CK. J. Org. Chem.  2003,  68:  9012 
    Google Scholar
  • 22 Hodgson DM. Witherington J. Moloney BA. J. Chem. Soc., Perkin Trans. 1  1993,  1543 
    CrossrefGoogle Scholar