PDF herunterladen
Synthesis 2011(17): 2810-2816  
DOI: 10.1055/s-0030-1260121
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Silver Triflate Catalyzed Reaction of 2-Alkynylbenzaldoxime with Phenol: A General and Facile Route to 1-Aroxyisoquinolines

Danqing Zhenga, Zhiyong Wang*b, Jie Wu*a,c
a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65641740; e-Mail: jie_wu@fudan.edu.cn;
b School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazhengjie Road, Chongqing 400044, P. R. of China
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
Weitere Informationen

Publikationsverlauf

Received 12 May 2011
Publikationsdatum:
14. Juli 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

2-Alkynylbenzaldoxime reacts with phenol under the catalysis of silver triflate in the presence of bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBroP) under mild conditions, leading to the formation of 1-aroxyisoquinolines in good to excellent yields.

Key words

cyclizations - isoquinoline - phosphorus ligands - phenol - silver triflate

    References

  • For selected recent examples, see:
  • 1a Li S. Wu J. Org. Lett.  2011,  13:  712 
    Google Scholar
  • 1b Chen Z. Zheng D. Wu J. Org. Lett.  2011,  13:  848 
    Google Scholar
  • 1c Luo Y. Pan X. Wu J. Org. Lett.  2011,  13:  1150 
    Google Scholar
  • 1d Luo Y. Hong L. Wu J. Chem. Commun.  2011,  47:  5298 
    Google Scholar
  • 1e Chen Z. Ye C. Gao L. Wu J. Chem. Commun.  2011,  47:  5623 
    Google Scholar
  • 1f Chen Z. Wu J. Org. Lett.  2010,  12:  4856 
    Google Scholar
  • 1g Chen Z. Yu X. Wu J. Chem. Commun.  2010,  46:  6356 
    Google Scholar
  • 1h Ye S. Yang X. Wu J. Chem. Commun.  2010,  46:  5238 
    Google Scholar
  • 1i Ye S. Yang X. Wu J. Chem. Commun.  2010,  46:  2950 
    Google Scholar
  • 2a Zheng G. Dwoskin LP. Deaciuc AG. Zhu J. Jones MD. Crooks PA. Bioorg. Med. Chem.  2005,  13:  3899 
    Google Scholar
  • 2b Wilson KJ. van Niel MB. Cooper L. Bloomfield D. O’Connor D. Fish LR. MacLeod AM. Bioorg. Med. Chem. Lett.  2007,  17:  2643 
    Google Scholar
  • 2c Campeau L.-C. Fagnou K. Chem. Soc. Rev.  2007,  36:  1058 
    Google Scholar
  • 2d Laird T. Org. Process Res. Dev.  2006,  10:  851 
    Google Scholar
  • For selected examples, see:
  • 3a Bentley KW. The Isoquinoline Alkaloids   Vol. 1:  Harwood Academic; Australia: 1998. 
    Google Scholar
  • 3b Trotter BW. Nanda KK. Kett NR. Regan CP. Lynch JJ. Stump GL. Kiss L. Wang J. Spencer RH. Kane SA. White RB. Zhang R. Anderson KD. Liverton NJ. McIntyre CJ. Beshore DC. Hartman GD. Dinsmore CJ. J. Med. Chem.  2006,  49:  6954 
    Google Scholar
  • 3c Ramesh P. Reddy NS. Venkateswarlu Y. J. Nat. Prod.  1999,  62:  780 
    Google Scholar
  • 3d Kaneda T. Takeuchi Y. Matsui H. Shimizu K. Urakawa N. Nakajyo S. J. Pharmacol. Sci.  2005,  98:  275 
    Google Scholar
  • 3e Marchand C. Antony S. Kohn KW. Cushman M. Ioanoviciu A. Staker BL. Burgin AB. Stewart L. Pommier Y. Mol. Cancer Ther.  2006,  5:  287 
    Google Scholar
  • 3f Balasubramanian M. Keay JG. In Comprehensive Heterocyclic Chemistry II   Vol. 5:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996.  p.245-300  
    Google Scholar
  • 3g Chrzanowska M. Rozwadowska MD. Chem. Rev.  2004,  104:  3341 
    Google Scholar
  • 4a Yang H. Tetrahedron Lett.  2009,  50:  3081 
    Google Scholar
  • 4b Smits RA. Lim HD. Hanzer A. Zuiderveld OP. Guaita E. Adami M. Coruzzi G. Leurs R. de Esch IJP. J. Med. Chem.  2008,  51:  2457 
    Google Scholar
  • 4c Fish PV. Barber CG. Brown DG. Butt R. Collis MG. Dickinson RP. Henry BT. Horne VA. Huggins JP. King E. O’Gara M. McCleverty D. McIntosh F. Phillips C. Webster R. J. Med. Chem.  2007,  50:  2341 
    Google Scholar
  • 4d Doherty S. Knight JG. McGrady JP. Ferguson AM. Ward NAB. Harrington RW. Adv. Synth. Catal.  2010,  352:  201 
    Google Scholar
  • 4e Lee BK. Biscoe MR. Buchwald SL. Tetrahedron Lett.  2009,  50:  3672 
    Google Scholar
  • 4f Shen Q. Ogata T. Hartwig JF. J. Am. Chem. Soc.  2008,  130:  6586 
    Google Scholar
  • 4g Chen G. Lam WH. Fok WS. Lee HW. Kwong FY. Chem. Asian J.  2007,  2:  306 
    Google Scholar
  • 4h Xie X. Zhang TY. Zhang Z. J. Org. Chem.  2006,  71:  6522 
    Google Scholar
  • 4i Shen Q. Shekhar S. Stambuli JP. Hartwig JF. Angew. Chem. Int. Ed.  2005,  44:  1371 
    Google Scholar
  • 4j Kumar K. Michalik D. Castro IG. Tillack A. Zapf A. Arlt M. Heinrich T. Böttcher H. Beller M. Chem. Eur. J.  2004,  10:  746 
    Google Scholar
  • 4k Burton G. Cao P. Li G. Rivero R. Org. Lett.  2003,  5:  4373 
    Google Scholar
  • 5 Gamage SA. Spicer JA. Rewcastle GW. Milton J. Sohal S. Dangerfield W. Mistry P. Vicker N. Charlton PA. Denny WA. J. Med. Chem.  2002,  45:  740 
    CrossrefGoogle Scholar
  • 6a Londregan AT. Jennings S. Wei L. Org. Lett.  2010,  12:  5254 
    Google Scholar
  • 6b Londregan AT. Jennings S. Wei L. Org. Lett.  2011,  13:  1840 
    Google Scholar
  • 7a Qiu G. Ding Q. Ren H. Peng Y. Wu J. Org. Lett.  2010,  12:  3975 
    Google Scholar
  • 7b Ren H. Luo Y. Ye S. Wu J. Org. Lett.  2011,  13:  2552 
    Google Scholar
  • 7c Ye S. Wang H. Wu J. ACS Comb. Sci.  2011,  13:  120 
    Google Scholar
  • 7d Ye S. Gao K. Wu J. Adv. Synth. Catal.  2010,  352:  1746 
    Google Scholar
  • 7e Ye S. Wang H. Wu J. Eur. J. Org. Chem.  2010,  6436 
    Google Scholar
  • 7f Chen Z. Yu X. Su M. Yang X. Wu J. Adv. Synth. Catal.  2009,  351:  2702 
    Google Scholar
  • 7g Ding Q. Wang Z. Wu J. J. Org. Chem.  2009,  74:  921 
    Google Scholar
  • 7h Ding Q. Wang Z. Wu J. Tetrahedron Lett.  2009,  50:  198 
    Google Scholar
  • 7i Ding Q. Wu J. Adv. Synth. Catal.  2008,  350:  1850 
    Google Scholar
  • 7j Zheng D. Chen Z. Liu J. Wu J. Org. Biomol. Chem.  2011,  9:  4763 
    Google Scholar
  • 8a Yeom H.-S. Lee J.-E. Shin S. Angew. Chem. Int. Ed.  2008,  47:  7040 
    Google Scholar
  • 8b Yeom H.-S. Kim S. Shin S. Synlett  2008,  924 
    Google Scholar
  • 8c Huo Z. Tomeba H. Yamamoto Y. Tetrahedron Lett.  2008,  49:  5531 
    Google Scholar
  • 9a Roesch KR. Larock RC. J. Org. Chem.  2002,  67:  86 
    Google Scholar
  • 9b MacNevin CJ. Moore RL. Liotta DC. J. Org. Chem.  2008,  73:  1264 
    Google Scholar