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Synthesis 2011(3): 377-386  
DOI: 10.1055/s-0030-1258392
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Synthesis of Methyl 7H-Dibenz[b,g]oxocin-6-carboxylates from Morita-Baylis-Hillman Adducts of 2-Phenoxybenzaldehydes

Sang-Hyun Ahn, Seung Soon Jang, Eun-Gu Han, Kee-Jung Lee*
Organic Synthesis Laboratory, Department of Chemical Engineering, Hanyang University, Seoul 133-791, South Korea
Fax: +82(2)22984101; e-Mail: leekj@hanyang.ac.kr ;
Further Information

Publication History

Received 19 August 2010
Publication Date:
05 January 2011 (online)

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Abstract

A new synthetic method for methyl 7H-dibenz[b,g]oxocin-6-carboxylates by Friedel-Crafts reaction of readily available bromides of Morita-Baylis-Hillman adducts with aluminum chloride has been developed.

Key words

Morita-Baylis-Hillman reaction - Friedel-Crafts reaction - methyl 7H-dibenz[b,g]oxocin-6-carboxylates - aluminum chloride - 2-phenoxybenzaldehydes

    References

  • For reviews of medium ring cyclic ethers, see:
  • 1a Elliott MC. Contemp. Org. Synth.  1994,  1:  457 
    Google Scholar
  • 1b Moody CJ. Davies MJ. In Studies in Natural Products Chemistry   Vol. 10:  . Elsevier; New York: 1992.  p.201 
    Google Scholar
  • 2 Harrison B. Crews P. J. Org. Chem.  1997,  62:  2646 
    CrossrefGoogle Scholar
  • 3a Macias FA. Varela RM. Torres A. Molinillo JMG. Fronzek FR. Tetrahedron Lett.  1993,  34:  1999 
    Google Scholar
  • 3b Macias FA. Molinillo JMG. Varela RM. Torres A. Fronezek FR. J. Org. Chem.  1994,  59:  8261 
    Google Scholar
  • 4a Venkateswaran RV. Sabui SK. Tetrahedron Lett.  2004,  45:  9653 
    Google Scholar
  • 4b Sen PK. Biswas B. Venkateswaran RV. Tetrahedron Lett.  2005,  46:  8741 
    Google Scholar
  • 4c Ghosh S. Tuhina K. Bhowmik DR. Venkateswaran RV. Tetrahedron  2007,  63:  644 
    Google Scholar
  • 4d Macias FA. Varela RM. Torres A. Molinillo JMG. Fronzek FR. J. Nat. Prod.  1999,  62:  1636 
    Google Scholar
  • 5 Nagai M. Nagumo S. Lee SM. Eguchi I. Kawai K. Chem. Pharm. Bull.  1986,  34:  1 
    CrossrefGoogle Scholar
  • 6a Nagai M. Nagumo S. Heterocycles  1986,  24:  601 
    Google Scholar
  • 6b Namikoshi M. Nakata H. Saitoh T. Chem. Pharm. Bull.  1987,  35:  3615 
    Google Scholar
  • 7 Nagai M. Nagumo S. Chem. Pharm. Bull.  1987,  35:  3002 
    CrossrefGoogle Scholar
  • 8 Nagai M. Nagumo S. Chem. Pharm. Bull.  1990,  38:  1490 
    CrossrefGoogle Scholar
  • 9 Stefinovic M. Snieckus V. J. Org. Chem.  1998,  63:  2808 
    CrossrefGoogle Scholar
  • 10a Nguyen VTH. Bellur E. Fischer C. Langer P. Tetrahedron  2007,  63:  8037 
    Google Scholar
  • 10b Nguyen VTH. Bellur E. Langer P. Tetrahedron Lett.  2006,  47:  113 
    Google Scholar
  • 11 Majumdar KC. Ray K. Debnath P. Maji PK. Kundu N. Tetrahedron Lett.  2008,  49:  5597 
    CrossrefGoogle Scholar
  • 12 Majumdar KC. Ansary I. Sinha B. Chattopadhyay B. Synthesis  2009,  3593 
    Article in Thieme ConnectGoogle Scholar
  • 13 Kasmai HS. Whitlock HW. J. Org. Chem.  1972,  37:  2162 
    Google Scholar
  • 14 Shapiro R. Slobodin D. J. Org. Chem.  1969,  34:  1165 
    CrossrefGoogle Scholar
  • 15 Anastassiou AG. Kasmai HS. Angew. Chem., Int. Ed. Engl.  1980,  19:  393 
    CrossrefGoogle Scholar
  • 16a Lim HN. Ji S.-H. Lee K.-J. Synthesis  2007,  2454 
    Google Scholar
  • 16b Jeon KJ. Lee K.-J. J. Heterocycl. Chem.  2008,  45:  615 
    Google Scholar
  • 16c Park SP. Song YS. Lee K.-J. Tetrahedron  2009,  65:  4703 
    Google Scholar
  • 17a Basavaiah D. Pandiaraju S. Padmaja K. Synlett  1996,  393 
    Google Scholar
  • 17b Lee HJ. Seong MR. Kim JN. Tetrahedron Lett.  1998,  39:  6223 
    Google Scholar
  • 17c Basavaiah D. Bakthadoss M. Reddy GJ. Synthesis  2001,  919 
    Google Scholar
  • 17d Basavaiah D. Reddy RM. Tetrahedron Lett.  2001,  42:  3025 
    Google Scholar
  • 17e Lee CG. Lee KY. Gowrisankar S. Kim JN. Tetrahedron Lett.  2004,  45:  7409 
    Google Scholar
  • 17f Lee CG. Lee KY. Lee S. Kim JN. Tetrahedron  2005,  61:  1493 
    Google Scholar
  • For reviews of the Morita-Baylis-Hillman reaction, see:
  • 18a Drewes SE. Roos GHP. Tetrahedron  1988,  44:  4653 
    Google Scholar
  • 18b Basavaiah D. Rao PD. Hyma RS. Tetrahedron  1996,  52:  8001 
    Google Scholar
  • 18c Ciganek E. Org. React.  1997,  51:  201 
    Google Scholar
  • 18d Langer P. Angew. Chem. Int. Ed.  2000,  39:  3049 
    Google Scholar
  • 18e Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev.  2003,  103:  811 
    Google Scholar
  • 18f Kataoka T. Kinoshita H. Eur. J. Org. Chem.  2005,  45 
    Google Scholar
  • 18g Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev.  2007,  36:  1581 
    Google Scholar
  • 18h Singh V. Batra S. Tetrahedron  2008,  64:  4511 
    Google Scholar
  • 18i Declerck V. Martinez J. Lamaty F. Chem. Rev.  2009,  109:  1 
    Google Scholar
  • 18j Ma G .-N. Jiang J.-J. Shi M. Wei Y. Chem. Commun.  2009,  5496 
    Google Scholar
  • 19a Yeager GW. Schissel DN. Synthesis  1995,  28 
    Google Scholar
  • 19b Zhao J. Yue D. Campo MA. Larock RC. J. Am. Chem. Soc.  2007,  129:  5288 
    Google Scholar
  • 21a Das B. Venkateswarlu K. Krishnaiah M. Holla H. Majhi A. Helv. Chim. Acta  2006,  89:  1417 
    Google Scholar
  • 21b Sá MM. Fernandes L. Ferreira M. Bortoluzzi AJ. Tetrahedron Lett.  2008,  49:  1228 
    Google Scholar
  • According to literature reports, in the ¹H NMR spectrum of methyl 2-bromomethyl-3-phenylprop-2-enoate, the methylene protons of Z- or E-form are known to resonate at δ = 4.40 or 4.23 ppm, respectively, see:
  • 22a Sheng S.-R. Wang Q. Wang Q.-Y. Guo L. Liu X.-L. Huang X. Synlett  2006,  1887 
    Google Scholar
  • 22b Basavaiah D. Reddy KR. Kumaragurubaran N. Nat. Protocols  2007,  2:  2665 
    Google Scholar
  • 23a Wang J.-Q. Harvey RG. Tetrahedron  2002,  58:  5927 
    Google Scholar
  • 23b Das SK. Singh R. Panda G. Eur. J. Org. Chem.  2009,  4757 
    Google Scholar
  • 23c Singh R. Panda G. Org. Biomol. Chem.  2010,  8:  1097 
    Google Scholar
  • 24 Anthony VM, Clough JM, Defraine P, Godfrey CRA, Crowley PJ, and Anderton K. inventors; European patent EP  243012.  ; Chem. Abstr. 1988, 108, 186581
20

Most of the MBH adduct was decomposed.

25

Some other intractable, unidentified, insoluble products were also formed.