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Synthesis 2011(4): 599-602  
DOI: 10.1055/s-0030-1258394
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Green Synthesis of Angularly Fused Furano-Pyrone/Coumarin and Quinolone Derivatives via Molecular Iodine-Mediated 5-exo-trig Cyclization in Aqueous Micelles

K. C. Majumdar*, Debankan Ghosh, Shovan Mondal
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
e-Mail: kcm_ku@yahoo.co.in;
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Publikationsverlauf

Received 18 November 2010
Publikationsdatum:
10. Januar 2011 (online)

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Abstract

A simple, economical, and green approach to the synthesis of angularly fused furano- pyrone/coumarin and quinolone derivatives by molecular iodine-mediated 5-exo-trig cyclization using sodium dodecyl sulfate (SDS) as surfactant in water is described.

Key words

iodine - water - cyclizations - surfactants

    References

  • 1 Wu J. Liao Y. Yang Z. J. Org. Chem.  2001,  66:  3642 
    CrossrefGoogle Scholar
  • 2a Raski SR. Williams RM. Chem. Rev.  1998,  98:  2723 
    Google Scholar
  • 2b Murakami A. Guo G. Omura M. Yano M. Ito C. Furukawa H. Takahasi D. Koshimizu K. Ohigashi H. Bioorg. Med. Chem. Lett.  2000,  10:  59 
    Google Scholar
  • 2c Guilet D. Helesbeux JJ. Seraphin D. Sevenet T. Richomme P. Bruneton J. J. Nat. Prod.  2001,  64:  563 
    Google Scholar
  • 2d Kang SY. Lee KY. Sung SH. Park MJ. Kim YC. J. Nat. Prod.  2001,  64:  683 
    Google Scholar
  • 3 Dall’Acqua F. Vedaldi D. In CRC Handbook of Organic Photochemistry and Photobiology   Horspool WM. Song PS. CRC Press; Boca Raton: 1995.  p.1341 
    Google Scholar
  • 4 Bethea D. Fullmer B. Syed S. Seltzer G. Tiano J. Rischko C. Gillespie L. Brown D. Gasparro FP. J. Dermatol. Sci.  1999,  19:  78 
    CrossrefGoogle Scholar
  • 5 Nagaiah K. Krupadanam GLD. Srimannarayana G. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1991,  30:  666 
    Google Scholar
  • 6a Bentley R. Zwitkowits PM. J. Am. Chem. Soc.  1967,  89:  676 
    Google Scholar
  • 6b Bentley R. Zwitkowits PM. J. Am. Chem. Soc.  1967,  89:  681 
    Google Scholar
  • 7a Cimino G. Sodano G. Spinella A. J. Org. Chem.  1987,  52:  5326 
    Google Scholar
  • 7b Ichihara A. Tazaki H. Sakamura S. Tetrahedron Lett.  1983,  24:  5373 
    Google Scholar
  • 7c Ichihara A. Miki M. Sakamura S. Tetrahedron Lett.  1985,  26:  2453 
    Google Scholar
  • 7d Shimizu S. Sakurai I. Yamamoto Y. Chem. Pharm. Bull.  1983,  31:  3781 
    Google Scholar
  • 7e Sakurai I. Shimizu S. Yamamoto Y. Chem. Pharm. Bull.  1988,  36:  1328 
    Google Scholar
  • 8a Omura S. Ohno H. Saheki T. Masakazu Y. Nakagawa A. Biochem. Biophys. Res. Commun.  1978,  83:  704 
    Google Scholar
  • 8b Ohno H. Saheki T. Awaya J. Nakagawa A. Omura S. J. Antibiot.  1978,  31:  1116 
    Google Scholar
  • 9a Groutas WC. Abrams WR. Carrol RT. Moi MK. Miller KE. Margolis MT. Experientia  1984,  40:  361 
    Google Scholar
  • 9b Groutas WC. Stanga MA. Brubaker MJ. Huang TL. Moi MK. Carrol RT. J. Med. Chem.  1985,  28:  1106 
    Google Scholar
  • 9c Spencer RW. Copp LJ. Pfister JR. J. Med. Chem.  1985,  28:  1828 
    Google Scholar
  • 9d Cook L. Ternai B. Ghosh P. J. Med. Chem.  1987,  30:  1017 
    Google Scholar
  • 10a Rehse K. Schinkel W. Siemann U. Arch. Pharm.  1980,  313:  344 
    Google Scholar
  • 10b Rehse K. Schinkel W. Arch. Pharm.  1983,  316:  845 
    Google Scholar
  • 10c Rehse K. Schinkel W. Arch. Pharm.  1983,  316:  988 
    Google Scholar
  • 10d Rehse K. Brandt F. Arch. Pharm.  1983,  316:  1030 
    Google Scholar
  • 11a Majumdar KC. Mondal S. Tetrahedron Lett.  2008,  49:  2418 
    Google Scholar
  • 11b Majumdar KC. Mondal S. De N. Synlett  2008,  2851 
    Google Scholar
  • 11c Majumdar KC. Mondal S. Ghosh D. Chattopadhyay B. Synthesis  2010,  3115 
    Google Scholar
  • 11d Majumdar KC. Mondal S. Ghosh D. Synthesis  2010,  1176 
    Google Scholar
  • 11e Majumdar KC. Mondal S. Ghosh D. Tetrahedron Lett.  2009,  50:  4781 
    Google Scholar
  • 11f Majumdar KC. Mondal S. De N. Synthesis  2009,  3127 
    Google Scholar
  • 11g Majumdar KC. Chakravorty S. De N. Tetrahedron Lett.  2008,  49:  3419 
    Google Scholar
  • 12 Chattopadhyay SK. Maity S. Srikanta Panja S. Tetrahedron Lett.  2002,  43:  7781 
    CrossrefGoogle Scholar
  • 13 Majumdar KC. Choudhury PK. Khan AT. Synth. Commun.  1989,  19:  3249 
    CrossrefGoogle Scholar
  • 14 Chattopadhyay SK. Dey R. Biswas S. Synthesis  2005,  403 
    Artikel in Thieme ConnectGoogle Scholar
  • 15 Majumdar KC. Basu PK. Roy B. Synth. Commun.  2003,  33:  3621 
    CrossrefGoogle Scholar
  • 16 Majumdar KC. Biswas A. Mukhopadhyay PP. Can. J. Chem.  2005,  83:  2046 
    CrossrefGoogle Scholar
  • 17 Tandon VK. Maurya HK. Tetrahedron Lett.  2010,  51:  3843 
    CrossrefGoogle Scholar
  • 18a Tandon VK. Maurya HK. Tetrahedron Lett.  2009,  50:  5896 
    Google Scholar
  • 18b Tandon VK. Maurya HK. Verma MK. Kumar R. Shukla PK. Eur. J. Med. Chem.  2010,  45:  2418 
    Google Scholar
  • 20 Yadav AK. Sing BK. Sing N. Tripathi RP. Tetrahedron Lett.  2007,  48:  6628 
    CrossrefGoogle Scholar
  • 21 Mahajan VA. Shinde PD. Gajare AS. Karthikeyan M. Wakharkar RD. Green Chem.  2002,  4:  325 
    CrossrefGoogle Scholar
19

Full crystallographic parameters for 2a have been deposited with the Cambridge Crystallographic Data Centre under reference number CCDC-800999.