Download PDF
Synthesis 2010(21): 3745-3754  
DOI: 10.1055/s-0030-1258236
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III)-Catalyzed Facile Synthesis of Dihydrobenzofuran-Tethered Pyridines and Dihydroquinolin-5(6H)-ones from β-Enaminones

Srinivas Kantevari*a, Dinesh Addlaa, Balasubramanian Sridharb
a Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500007, India
e-Mail: kantevari@yahoo.com; e-Mail: kantevari@gmail.com;
b Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500007, India
Further Information

Publication History

Received 29 June 2010
Publication Date:
30 August 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of novel dihydrobenzofuran-tethered pyridines, dihydroquinolin-5(6H)-ones, and indeno[1,2-b]pyridin-5-ones were synthesized in very good yields by CeCl3˙7H2O-NaI catalyzed one-pot condensation of variants of the Bohlmann-Rahtz reaction, viz. β-enaminones derived from 7-acetyldihydrobenzofurans, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. The protocol offers the advantages of easily accessible substrates, shorter reaction times, and easy work-up with a readily available catalyst. Further more, dihydrobenzofuran-substituted 2-(chloromethyl)pyridine was derivatized to its synthetic hybrid by reacting with piperazine.

Key words

Bohlmann-Rahtz reaction - dihydrobenzofuran - CeCl3˙7H2O-NaI - one-pot condensation - β-enaminone - hetero­cycles - pyridines - quinolinones

    References

  • 1a Spandl RJ. Bender A. Spring DR. Org. Biomol. Chem.  2008,  6:  1149 
    Google Scholar
  • 1b Tan DS. Nat. Chem. Biol.  2005,  1:  74 
    Google Scholar
  • 1c Bagley MC. Dale JW. Merritt EA. Xiong X. Chem. Rev.  2005,  105:  685 
    Google Scholar
  • 1d Burke MD. Schreiber SL. Angew. Chem. Int. Ed.  2004,  43:  46 
    Google Scholar
  • 1e Henry GD. Tetrahedron  2004,  60:  6043 
    Google Scholar
  • 2a Aulakh VS. Ciufolini MA. J. Org. Chem.  2009,  74:  5750 
    Google Scholar
  • 2b Bagley MC. Chapaneri K. Dale JW. Xiong X. Bower J. J. Org. Chem.  2005,  70:  1389 
    Google Scholar
  • 2c Bagley MC. Xiong X. Org. Lett.  2004,  6:  3401 
    Google Scholar
  • 2d Bagley MC. Dale JW. Xiong X. Bower J. Org. Lett.  2003,  5:  4421 
    Google Scholar
  • 2e Bagley MC. Dale JW. Ohnesorge M. Xiong X. Bower J. J. Comb. Chem.  2003,  5:  41 
    Google Scholar
  • 2f Bagley MC. Bashford KE. Hesketh CL. Moody CJ. J. Am. Chem. Soc.  2000,  122:  3301 
    Google Scholar
  • For streptonigrin:
  • 3a Harding MM. Long GV. Brown CL. J. Med. Chem.  1993,  36:  3056 
    Google Scholar
  • For cerivastatin:
  • 3b Angerbauer R. Bischoff H. Steinke W. Ritter W. Drugs Future  1994,  19:  537 
    Google Scholar
  • 3c Chen B.-C. Bednarz MS. Zhang H. Guo P. Jemal M. Robl JA. Biller SA. Sundeen JE. Balasubramanian B. Barrish JC.
    J. Labelled Compd. Radiopharm.  2006,  49:  311 
    Google Scholar
  • For lavendamycin:
  • 3d Hassani M. Cai W. Holley DC. Lineswala JP. Maharjan BR. Ebrahimian GR. Seradj H. Stocksdale MG. Mohammadi F. Marvin CC. Gerdes JM. Beall HD. Behforouz M. J. Med. Chem.  2005,  48:  7733 
    Google Scholar
  • 4 For a review of the chemistry and synthesis of benzofurans, see: Hou X.-L. Yang Z. Wong HNC. Furans and Benzofurans, In Progress in Heterocyclic Chemistry   Vol. 14:  Gribble GW. Gilchrist TL. Pergamon; Oxford: 2002.  p.139-179  
    CrossrefGoogle Scholar
  • 5a Lu B. Wang B. Zhang Y. Ma D. J. Org. Chem.  2007,  72:  5337 
    Google Scholar
  • 5b Hagihara K. Kashima H. Iida K. Enokizono J. Uchida S.-i. Nonaka H. Kurokawa M. Shimada J. Bioorg. Med. Chem. Lett.  2007,  17:  1616 
    Google Scholar
  • 5c Dixit M. Sharon A. Maulik PR. Goel A. Synlett  2006,  1497 
    Google Scholar
  • 5d Wyatt PG. Allen MJ. Chilcott J. Gardner CJ. Livermore DG. Mordaunt JE. Nerozzi F. Patel M. Perren MJ. Weingarten GG. Shabbir S. Woollard PM. Zhou P. Bioorg. Med. Chem. Lett.  2002,  12:  1405 
    Google Scholar
  • For recent reviews and books see:
  • 6a Sunderhaus JD. Martin SF. Chem. Eur. J.  2009,  15:  1300 
    Google Scholar
  • 6b Ramon DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 
    Google Scholar
  • 6c Domling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 6d Multicomponent Reactions   Zhu J. Bienaymé H. Wiley; Weinheim: 2005. 
    Google Scholar
  • 6e Ramon DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 
    Google Scholar
  • 6f Banfi L. Riva R. Org. React.  2005,  65:  1 
    Google Scholar
  • 6g Hulme C. Gore V. Curr. Med. Chem.  2003,  10:  51 
    Google Scholar
  • 7a Ganem B. Acc. Chem. Res.  2009,  42:  463 
    Google Scholar
  • 7b Zhu W. Mena M. Jnoff E. Pasau P. Ghosez L. Angew. Chem. Int. Ed.  2009,  48:  5880 
    Google Scholar
  • 7c Elders N. van der Born D. Hendrickx LJD. Timmer BJJ. Krause A. Janssen E. de Kanter FJJ. Ruijter E. Orru RVA. Angew. Chem. Int. Ed.  2009,  48:  5856 
    Google Scholar
  • 8a Bagley MC. Glover G. Merritt EA. Synlett  2007,  2459 
    Google Scholar
  • 8b Merritt EA. Bagley MC. Synlett  2007,  954 
    Google Scholar
  • 8c Bohlmann F. Rahtz D. Chem. Ber.  1957,  90:  2265 
    Google Scholar
  • 9a Kantevari S. Chary MV. Vuppalapati SVN. Tetrahedron  2007,  63:  13024 
    Google Scholar
  • 9b Kantevari S. Chary MV. Vuppalapati SVN. Lingaiah N. J. Heterocycl. Chem.  2008,  1009 
    Google Scholar
  • 10a Wan J.-P. Pan Y.-J. Chem. Commun.  2009,  2768 
    Google Scholar
  • 10b Alnajjar A. Abdelkhalik MM. Al-Enezi A. Elnagdi MH. Molecules  2009,  14:  68 
    Google Scholar
  • 10c Riyadh SM. Abdelhamid IA. Al-Matar HM. Hilmy NM. Elnagdi MH. Heterocycles  2008,  75:  1849 
    Google Scholar
  • 10d Lieby-Muller F. Allais C. Constantieux T. Rodriguez J. Chem. Commun.  2008,  4207 
    Google Scholar
  • 10e Senaiar RS. Young DD. Deiters A. Chem. Commun.  2006,  1313 
    Google Scholar
  • 10f Davis JM. Truong A. Hamilton AD. Org. Lett.  2005,  7:  5405 
    Google Scholar
  • 10g Bashford KE. Burton MB. Cameron S. Cooper AL. Hogg RD. Kane PD. MacManus DA. Matrunola CA. Moody CJ. Robertson AAB. Warne MR. Tetrahedron Lett.  2003,  44:  1627 
    Google Scholar
  • 10h Al-Saleh B. Abdelkhalik MM. Eltoukhy AM. Elnagdi MH. J. Heterocycl. Chem.  2002,  39:  1035 
    Google Scholar
  • 10i Omran FA. Awadi NA. Khair AAE. Elnagdi MH. Org. Prep. Proced. Int.  1997,  29:  285 
    Google Scholar
  • 11a Tambade PJ. Patil YP. Bhanage BM. Curr. Org. Chem.  2009,  13:  1805 
    Google Scholar
  • 11b Comelles J. Moreno-Mañas M. Vallribera A. ARKIVOC  2005,  ix:  207 ; http://www.arkat-usa.org/home
    Google Scholar
  • 12a Bartoli G. Marcantoni E. Sambri L. Synlett  2003,  2101 
    Google Scholar
  • 12b Bartoli G. Fernández-Bolaños JG. Antonio GD. Foglia G. Giuli S. Gunnella R. Mancinelli M. Marcantoni E. Paoletti M. J. Org. Chem.  2007,  72:  6029 
    Google Scholar
  • 12c Khodaei MH. Khosropour AR. Kookhazadeh M. Synlett  2004,  1980 
    Google Scholar
  • 12d Christofeers J. Kauf T. Werner T. Rossle M. Eur. J. Org. Chem.  2006,  2601 
    Google Scholar
  • 12e Sabitha G. Reddy GSKK. Reddy KB. Reddy NM. Yadav JS. Adv. Synth. Catal.  2004,  346:  921 
    Google Scholar
  • 12f Sabitha G. Babu RS. Rajkumar M. Srividya R. Yadav JS. Org. Lett.  2002,  4:  343 
    Google Scholar
  • 13 Huang Z. Zhao Q. Huang R. Wang Q. Lett. Org. Chem.  2009,  6:  29 
    CrossrefGoogle Scholar
14

CCDC-771475 (3aa) and CCDC-771476 (3ae) contain the crystallographic data and can be obtained free of charge from the Cambridge Crystallographic Data centre via www.ccdc.cam.ac.uk/data_request/cif.