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Synthesis 2010(3): 486-492  
DOI: 10.1055/s-0029-1217143
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Tandem Synthesis of Furo[3,2-h]quinolines by a Sonogashira Cross-Coupling and Cyclization Reaction Supported by Basic Alumina Under Microwave Irradiation

Pritam Saha, Subhendu Naskar, Rupankar Paira, Shyamal Mondal, Arindam Maity, Krishnendu B. Sahu, Priyankar Paira, Abhijit Hazra, Diptendu Bhattacharya, Sukdeb Banerjee, Nirup B. Mondal*
Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India
Fax: +91(33)24735197; e-Mail: nirup@iicb.res.in;
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Publication History

Received 24 September 2009
Publication Date:
24 November 2009 (online)

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Abstract

Acetylenic 8-quinolinols generated in situ by the Sonogashira cross-coupling reaction are efficiently converted into furo[3,2-h]quinolines by microwave-assisted, copper-catalyzed, intramolecular cyclization in the presence of basic alumina.

Key words

heterocycles - furoquinoline - cross-coupling - cyclizations - solid-phase synthesis - microwave irradiation

    Reference

  • 1a Worlikar SA. Kesharwani T. Yao T. Larock RC. J. Org. Chem.  2007,  72:  1347 ; and references cited therein
    Google Scholar
  • 1b Alves D. Luchese C. Nogueira CW. Zeni G. J. Org. Chem.  2007,  72:  6726 
    Google Scholar
  • 1c Lamanna G. Menichetti S. Adv. Synth. Catal.  2007,  349:  2188 
    Google Scholar
  • 1d Fischer D. Tomeba H. Pahadi NK. Patil NT. Yamamoto Y. Angew. Chem. Int. Ed.  2007,  46:  4764 
    Google Scholar
  • 1e Hoedt WMR. Koten GV. Noltes JG. Synth. Commun.  1977,  7:  61 
    Google Scholar
  • 1f Barluenga J. Trincado M. Rubio E. González JM. Angew. Chem. Int. Ed.  2003,  42:  2406 
    Google Scholar
  • 1g Amjad M. Knight DW. Tetrahedron Lett.  2004,  45:  539 
    Google Scholar
  • 1h Hessian KO. Flynn BL. Org. Lett.  2006,  8:  243 
    Google Scholar
  • 1i Yue D. Yao T. Larock RC. J. Org. Chem.  2006,  71:  62 
    Google Scholar
  • 2a Banwell MG. Flynn BL. Hamel E. Wills AC. Aust. J. Chem.  1999,  52:  767 
    Google Scholar
  • 2b Arcadi A. Cacchi S. Fabrizi G. Marinelli F. Moro L. Synlett  1999,  1432 
    Google Scholar
  • 2c Flynn BL. Verdier-Pinard P. Hamel E. Org. Lett.  2001,  3:  651 
    Google Scholar
  • 2d Yue D. Larock RC. J. Org. Chem.  2002,  67:  1905 
    Google Scholar
  • 2e Larock RC. Yue D. Tetrahedron Lett.  2001,  42:  6011 
    Google Scholar
  • 2f Hessian KO. Flynn BL. Org. Lett.  2003,  5:  4377 
    Google Scholar
  • 2g Kesharwani T. Worlikar SA. Larock RC. J. Org. Chem.  2006,  71:  2307 
    Google Scholar
  • 2h Bui CT. Flynn BF. J. Comb. Chem.  2006,  8:  163 
    Google Scholar
  • 3a Zhu J. Eur. J. Org. Chem.  2003,  1133 
    Google Scholar
  • 3b Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  6:  3321 
    Google Scholar
  • 3c Döemling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 3d Weber L. Illgen K. Almstetter M. Synlett  1999,  366 
    Google Scholar
  • 3e Dax SL. McNally JJ. Youngman MA. Curr. Med. Chem.  1999,  6:  255 
    Google Scholar
  • 3f Armstrong RW. Combs AP. Tempest PA. Brown SD. Keating TA. Acc. Chem. Res.  1996,  29:  123 
    Google Scholar
  • 4 Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • 5a Ganêt J.-P. Blart E. Savignac M. Synlett  1992,  715 
    Google Scholar
  • 5b Alami M. Ferri F. Linstrumelle G. Tetrahedron Lett.  1993,  34:  6403 
    Google Scholar
  • 5c Böhm VPW. Herrmann WA. Eur. J. Org. Chem.  2000,  34:  3679 
    Google Scholar
  • 5d Choudary BM. Madhi S. Chowdari ML. Kantam B. Sreedhar B. J. Am. Chem. Soc.  2002,  124:  14127 
    Google Scholar
  • 5e Djakovitch L. Rollet P. Tetrahedron Lett.  2004,  45:  1367 
    Google Scholar
  • 6a Biffis A. Scattolin E. Ravasio N. Zaccheria F. Tetrahedron Lett.  2007,  48:  8761 
    Google Scholar
  • 6b Carril M. Correa A. Bolm C. Angew. Chem. Int. Ed.  2008,  47:  4862 
    Google Scholar
  • 6c Cheng J. Sun Y. Wang F. Guo M. Xu J.-H. Pan Y. Zhang Z. J. Org. Chem.  2004,  69:  5428 
    Google Scholar
  • 6d Urgaonkar S. Verkade JG. J. Org. Chem.  2004,  69:  5752 
    Google Scholar
  • 6e Garg NK. Woodroofe CC. Lacenere CJ. Quake SR. Stolz BM. Chem. Commun.  2005,  69:  4551 
    Google Scholar
  • 6f Erdélyi M. Gogoll A. J. Org. Chem.  2003,  68:  6431 
    Google Scholar
  • 7a Flnaru A. Berthault A. Besson T. Guillaumet G. Berteina-Raboin S. Org. Lett.  2002,  4:  2613 
    Google Scholar
  • 7b Jiang JZ. Wei YA. Cai C. J. Colloid Interface Sci.  2007,  312:  439 
    Google Scholar
  • 7c Jiang JZ. Cai C. J. Colloid Interface Sci.  2007,  307:  300 
    Google Scholar
  • 7d Majumdar KC. Samanta S. Chattopadhyay B. Tetrahedron Lett.  2008,  49:  7213 
    Google Scholar
  • 7e Eckhardt M. Fu GC. J. Am. Chem. Soc.  2003,  125:  13642 
    Google Scholar
  • 8a Dallinger D. Kappe CO. Chem. Rev.  2007,  107:  2563 
    Google Scholar
  • 8b Appukkuttan P. Eycken EV. Eur. J. Org. Chem.  2008,  1133 
    Google Scholar
  • 8c Leadbeater NE. Marco M. Org. Lett.  2002,  4:  2973 
    Google Scholar
  • 8d Leadbeater NE. Marco M. Angew. Chem. Int. Ed.  2003,  42:  1407 
    Google Scholar
  • 8e Kabalka GW. Wang L. Pagni RM. Tetrahedron  2001,  57:  8017 
    Google Scholar
  • 8f Okuro K. Furuune M. Enna M. Miura M. Nomura M. J. Org. Chem.  1993,  58:  4716 
    Google Scholar
  • 8g Wang J.-X. Liu Z. Hu Y. Wei B. Kang L. Synth. Commun.  2002,  32:  1937 
    Google Scholar
  • 9a Bates CG. Saejueng P. Murphy JM. Venkataraman D. Org. Lett.  2002,  4:  4727 
    Google Scholar
  • 9b Dai WM. Lai KW. Tetrahedron Lett.  2002,  43:  9377 
    Google Scholar
  • 10 Arcadi A. Cacchi S. Di Giuseppe S. Fabrizi G. Marinelli F. Synlett  2002,  453 
    Article in Thieme ConnectGoogle Scholar
  • 11a Grundon MF. McCorkindale NJ. J. Chem. Soc.  1957,  2177 
    Google Scholar
  • 11b Chamberlain TR. Grundon MF. J. Chem. Soc. C  1971,  910 
    Google Scholar
  • 12a Petit-Pali G. Rideau M. Chenieux JC. Planta Med. Phytother.  1982,  16:  55 
    Google Scholar
  • 12b Svoboda GH. Poore GH. Simpson PJ. Boder GB. J. Pharm. Sci.  1966,  55:  758 
    Google Scholar
  • 12c Wolters B. Eilert U. Planta Med.  1981,  42 (6):  137 
    Google Scholar
  • 12d Basco LK. Mitaku S. Skaltsounis AL. Ravelomanantsoa N. Tillequin F. Koch M. Le Bras J. Antimicrob. Agents Chemother.  1994,  38:  1169 
    Google Scholar
  • 13 Cironi P. Tulla-Puche J. Barany G. Albericio F. Álvarez M. Org. Lett.  2004,  6:  1405 
    CrossrefGoogle Scholar
  • 14a Saha P. Naskar S. Paira P. Hazra A. Sahu KB. Paira R. Banerjee S. Mondal NB. Green Chem.  2009,  11:  931 
    Google Scholar
  • 14b Varma RS. Green Chem.  1999,  1:  43 
    Google Scholar
  • 14c Fleckenstein A. Plenio H. Green Chem.  2007,  9:  1287 
    Google Scholar
  • 14d Phan NTS. Styring P. Green Chem.  2008,  10:  1055 
    Google Scholar
  • 15 Baldwin JE. J. Chem. Soc., Chem. Commun.  1976,  734 
    CrossrefGoogle Scholar