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Synthesis 2005(16): 2739-2743  
DOI: 10.1055/s-2005-872124
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of cis-Isoquinolonic Acids Containing Boronate Esters

Haiwen Zhanga, Christopher M. Vogelsa, Susan L. Wheatona, Felix J. Baerlocherb, Andreas Deckenc, Stephen A. Westcott*a
a Department of Chemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada
Fax: +1(506)3642313; e-Mail: swestcott@mta.ca;
b Department of Biology, Mount Allison University, Sackville, NB E4L 1G7, Canada
c Department of Chemistry, University of New Brunswick, Fredericton, NB E3B 5A3, Canada
Further Information

Publication History

Received 10 April 2005
Publication Date:
04 August 2005 (online)

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Abstract

The addition of homophthalic anhydride to aldimines derived from pinacolation of 4-formylphenylboronic acid selectively gives the corresponding cis-isoquinolonic acids. Reactions proceed without the need for an additional Lewis acid catalyst at room temperature.

Key words

aldimines - antifungal - boronate esters - cyclocondensation - isoquinolines

    References

  • 1 Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 2 Ni W. Fang H. Springsteen G. Wang B. J. Org. Chem.  2004,  69:  1999 
    CrossrefGoogle Scholar
  • 3 Yang W. Gao X. Wang B. Med. Res. Rev.  2003,  23:  346 
    CrossrefGoogle Scholar
  • 4 Kumar SK. Hager E. Pettit C. Gurulingappa H. Davidson NE. Khan SR. J. Med. Chem.  2003,  46:  2813 
    CrossrefGoogle Scholar
  • 5 Cama E. Colleluori DM. Emig FA. Shin H. Kim SW. Kim NN. Traish AM. Ash DE. Christianson DW. Biochemistry  2003,  42:  8445 
    CrossrefGoogle Scholar
  • 6 Stolowitz ML. Ahlem C. Hughes KA. Kaiser RJ. Kesicki EA. Li G. Lund KP. Torkelson SM. Wiley JP. Bioconjugate Chem.  2001,  12:  229 
    CrossrefGoogle Scholar
  • 7 Kabalka GW. Das BC. Das S. Tetrahedron Lett.  2001,  42:  7145 
    CrossrefGoogle Scholar
  • 8 Soloway AH. Tjarks W. Barnum BA. Rong F.-G. Barth RF. Codogni IM. Wilson JG. Chem. Rev.  1998,  98:  1515 
    CrossrefPubMedGoogle Scholar
  • 9 Weston GS. Blazquez J. Baquero F. Shoichet BK. J. Med. Chem.  1998,  41:  4577 
    CrossrefGoogle Scholar
  • 10a Vogels CM. Nikolcheva LG. Spinney HA. Norman DW. Baerlocher MO. Baerlocher FJ. Westcott SA. Can. J. Chem.  2001,  79:  1115 
    CrossrefGoogle Scholar
  • 10b Irving AM. Vogels CM. Nikolcheva LG. Edwards JP. He X.-F. Hamilton MG. Baerlocher MO. Baerlocher FJ. Decken A. Westcott SA. New J. Chem.  2003,  27:  1419 
    CrossrefGoogle Scholar
  • 11 Gronowitz S. Dalgren T. Namtvedt J. Roos C. Sjöberg B. Forsgren U. Acta Pharm. Suec.  1971,  8:  377 
    Google Scholar
  • 12 Chern M.-S. Li W.-R. Tetrahedron Lett.  2004,  45:  8323 
    CrossrefGoogle Scholar
  • 13 Povarov LS. Russ. Chem. Rev.  1967,  36:  656 
    CrossrefGoogle Scholar
  • 14 Yamada N. Kadowaki S. Takahashi K. Umezu K. Biochem. Pharmacol.  1992,  44:  1211 
    CrossrefPubMedGoogle Scholar
  • 15 Johnson JV. Rauckman S. Baccanari PD. Roth B. J. Med. Chem.  1989,  32:  1942 
    CrossrefGoogle Scholar
  • 16 Yadav JS. Reddy BVS. Saritha Raj K. Prasad AR. Tetrahedron  2003,  59:  1805 
    CrossrefGoogle Scholar
  • 17 Cushman M. Chen LG. J. Org. Chem.  1978,  43:  286 
    CrossrefGoogle Scholar
  • 18 Govindachari TR. Cinnasamy P. Rajeswari S. Chandrasekaran S. Pramila MS. Natarajan S. Nagarajan K. Pai BR. Heterocycles  1984,  22:  585 
    CrossrefGoogle Scholar
  • 19 Bogdanov MG. Palamareva MD. Tetrahedron  2004,  60:  2525 
    CrossrefGoogle Scholar
  • 20 Martichonok V. Jones JB. J. Am. Chem. Soc.  1996,  118:  950 
    CrossrefGoogle Scholar
  • 21 Moore ANJ. Wayner DDM. Can. J. Chem.  1999,  77:  681 
    CrossrefGoogle Scholar
  • 22 Hartley JH. Phillips MD. James TD. New J. Chem.  2002,  26:  1228 
    CrossrefGoogle Scholar
  • 23 Sailes HE. Watts JP. Whiting A. Tetrahedron Lett.  2000,  41:  2457 
    CrossrefGoogle Scholar
  • 24 Kaneti J. Bakalova SM. Pojarlieff IG. J. Org. Chem.  2003,  68:  6824 
    CrossrefGoogle Scholar
  • 25 Cushman M. Gentry J. Dekow FW. J. Org. Chem.  1977,  42:  1111 
    CrossrefPubMedGoogle Scholar
  • 26 Nöth H. Wrackmeyer B. In Nuclear Magnetic Resonance Spectroscopy of Boron Compounds   Springer-Verlag; Berlin: 1987. 
    Google Scholar
  • 27 Höpfl H. Sánchez M. Barba V. Farfán N. Rojas S. Santillan R. Inorg. Chem.  1998,  37:  1679 
    CrossrefGoogle Scholar
  • 28 Georgieva A. Stanoeva E. Karamfilova K. Spassov S. Angelova O. Haimova M. De Kimpe N. Boelens M. Tetrahedron  1994,  50:  9399 
    CrossrefGoogle Scholar
  • 29 Coapes RB. Souza FES. Fox MA. Batsanov AS. Goeta AE. Yufit DS. Leech MA. Howard JAK. Scott AJ. Clegg W. Marder TB. J. Chem. Soc., Dalton Trans.  2001,  1201 
    CrossrefGoogle Scholar
  • 30 Clegg W. Elsegood MRJ. Lawlor FJ. Norman NC. Pickett NL. Robbins EG. Scott AJ. Nguyen P. Taylor NJ. Marder TB. Inorg. Chem.  1998,  37:  5289 
    CrossrefGoogle Scholar
  • 31 Nguyen P. Coapes RB. Woodward AD. Taylor NJ. Burke JM. Howard JAK. Marder TB. J. Organomet. Chem.  2002,  652:  77 
    CrossrefGoogle Scholar
  • 32 Iwasa K. Moriyasu M. Tachibana Y. Kim H.-S. Wataya Y. Wiegrebe W. Bastow KF. Costentino LM. Kozuka M. Lee K.-H. Bioorg. Med. Chem.  2001,  9:  2871 
    CrossrefGoogle Scholar
  • 33 Bringmann G. Günther C. Peters E.-M. Peters K. Tetrahedron  2001,  57:  1253 
    CrossrefGoogle Scholar
  • 34 Gößnitzer E. Punkenhofer A. Amon A. Favre B. Eur. J. Pharm. Sci.  2003,  19:  151 
    CrossrefGoogle Scholar
  • 35 Barrett AGM. Seefeld MA. White AJP. Williams DJ. J. Org. Chem.  1996,  61:  2677 
    CrossrefGoogle Scholar
  • 36 Baerlocher FJ. Baerlocher MO. Chaulk CL. Langler RF. MacQuarrie SL. Aust. J. Chem.  2000,  53:  399 
    CrossrefGoogle Scholar
  • 37 SAINT 6.02   Bruker AXS, Inc.; Madison, Wisconsin, USA: 1997-1999. 
    Google Scholar
  • 38 Sheldrick GM. SADABS   Bruker AXS, Inc.; Madison, Wisconsin, USA: 1999. 
    Google Scholar
  • 39 Sheldrick GM. SHELXTL 5.1   Bruker AXS, Inc.; Madison, Wisconsin, USA: 1997. 
    Google Scholar