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Synlett 2009(5): 763-766  
DOI: 10.1055/s-0028-1087938
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

AuCl3-Catalyzed Tandem Reaction of N-(o-Alkynylphenyl)imines: A Modular Entry to Polycyclic Frameworks Containing an Indole Unit

Weijun Fua, Chen Xua, Guanglong Zoub, Dongfeng Honga, Dongsheng Denga, Zhiqiang Wanga, Baoming Ji*a
a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China
Fax: +86(379)655821; e-Mail: lyhxxjbm@lynu.edu.cn;
b School of Chemistry and Environmental Science, Guizhou University for Nationalities, Guiyang 550025, P. R. of China
Further Information

Publication History

Received 3 October 2008
Publication Date:
24 February 2009 (online)

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Abstract

A highly efficient tandem cyclization reaction of N-(o-alkynylphenyl)imines leading to ring-fused indoles was developed by using gold(III) as a catalyst under extremely mild reaction conditions.

Key words

cyclization - gold - indoles - N-(o-alkynylphenyl)imines

    References and Notes

  • For reviews on indole chemistry, see:
  • 1a Sundberg RL. Indoles   Academic Press; London: 1996. 
    Google Scholar
  • 1b Katritzky AR. Pozharskii AF. Handbook of Heterocyclic Chemistry   Pergamon Press; Oxford: 2000.  p.Chap. 4 
    Google Scholar
  • 1c Joule JA. In Science of Synthesis (Houben-Weyl: Methods of Molecular Transformations)   Vol. 10:  Thomas EJ. Thieme; Stuttgart: 2000. 
    Google Scholar
  • 1d For other references, see: Li JJ. Gribble GW. In Palladium in Heterocyclic Chemistry   Pergamon; Oxford: 2000.  p.Chap. 3 
    Google Scholar
  • 1e Gribble GW. J. Chem. Soc., Perkin Trans. 1  2000,  1045 
    Google Scholar
  • 1f Gribble GW. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; Oxford: 1996. 
    Google Scholar
  • 2a Sundberg RJ. In Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamon Press; Oxford: 1984. 
    Google Scholar
  • 2b Shriner RL. Ashley WC. Welch E. Org. Synth., Coll. Vol. III   Wiley; New York: 1955.  p.725-727  ; and references therein
    Google Scholar
  • 2c Rogers CU. Corson BB. Org. Synth., Coll. Vol. IV   Wiley; New York: 1963.  p.884 
    Google Scholar
  • 3 Noland WE. Baude FJ. Org. Synth. Collect. Vol. V   Wiley; New York: 1973.  p.567 
    Google Scholar
  • 4 Tyson FT. Org. Synth. Collect. Vol. III   Wiley; New York: 1955.  p.479 
    Google Scholar
  • For review on the palladium-catalyzed indole synthesis, see:
  • 5a For selected examples, see: Cacchi S. Fabrizi G. Chem. Rev.  2005,  105:  2873 
    Google Scholar
  • 5b Pal M. Subramanian V. Batchu VR. Dager I. Synlett  2004,  1965 
    Google Scholar
  • 5c Kabalka GW. Wang L. Pagni RM. Tetrahedron  2001,  57:  8017 
    Google Scholar
  • 5d Hong KB. Lee CW. Yum EK. Tetrahedron Lett.  2004,  45:  693 
    Google Scholar
  • 5e Yu MS. Leon LL. McGuire MA. Botha G. Tetrahedron Lett.  1998,  39:  9347 
    Google Scholar
  • 5f Watanabe M. Yamamoto T. Nishiyama M. Angew. Chem. Int. Ed.  2000,  39:  2501 
    Google Scholar
  • 5g Overman LE. Paone DV. Stearns BA. J. Am. Chem. Soc.  1999,  121:  7702 
    Google Scholar
  • 5h Roesch KR. Larock RC. J. Org. Chem.  2001,  66:  412 
    Google Scholar
  • 5i Yamazaki K. Kondo Y. Chem. Commun.  2002,  210 
    Google Scholar
  • For transition-metal-catalyzed cyclizations in indole synthesis, see the following: Cu(I):
  • 6a Ezquerra J. Pedregal C. Lamas C. J. Org. Chem.  1996,  61:  5804 
    Google Scholar
  • 6b Cu(II): Nishikawa T. Ishikawa M. Isobe M. Synlett  1999,  123 
    Google Scholar
  • 6c Saulnier MG. Frennesson DB. Deshpande MS. Vyas DM. Tetrahedron Lett.  1995,  36:  7841 
    Google Scholar
  • 6d Hg(stoichiometric): Hiroya K. Itoh S. Ozawa M. Kanamori Y. Sakamoto T. Tetrahedron Lett.  2002,  43:  1277 
    Google Scholar
  • 6e Larock RC. Harrison LW. J. Am. Chem. Soc.  1984,  106:  4218 
    Google Scholar
  • 7a Hiroya K. Itoh S. Ozawa M. J. Org. Chem.  2004,  69:  1126 
    Google Scholar
  • 7b Hiroya K. Itoh S. Ozawa M. Kanamori Y. Sakamoto T. Tetrahedron Lett.  2002,  43:  1277 
    Google Scholar
  • 8a Kamijo S. Yamamoto Y. J. Am. Chem. Soc.  2002,  124:  11940 
    Google Scholar
  • 8b Takeda A. Kamijo S. Yamamoto Y. J. Am. Chem. Soc.  2000,  122:  5662 
    Google Scholar
  • 8c Kamijo S. Yamamoto Y. Angew. Chem. Int. Ed.  2002,  41:  3230 
    Google Scholar
  • 8d Kamijo S. Yamamoto Y. J. Org. Chem.  2003,  68:  4764 
    Google Scholar
  • For reviews on gold-catalyzed reactions, see:
  • 9a Hashmi ASK. Hutchings GJ. Angew. Chem. Int. Ed.  2006,  45:  7896 
    Google Scholar
  • 9b Zhang L. Sun J. Kozmin SA. Adv. Synth. Catal.  2006,  348:  2271 
    Google Scholar
  • 9c Fürstner A. Davies PW. Angew. Chem. Int. Ed.  2007,  46:  3410 
    Google Scholar
  • 9d Jimenez-Nunez E. Echavarren AM. Chem. Commun.  2007,  333 
    Google Scholar
  • 9e Gorin DJ. Toste FD. Nature (London)  2007,  446:  395 
    Google Scholar
  • 9f Hashmi ASK. Chem. Rev.  2007,  107:  3180 
    Google Scholar
  • 9g Marion N. Nolan SP. Angew. Chem. Int. Ed.  2007,  46:  2750 
    Google Scholar
  • 9h Hashmi ASK. Nature (London)  2007,  449:  292 
    Google Scholar
  • 9i Dyker G. Angew. Chem. Int. Ed.  2000,  39:  4237 
    Google Scholar
  • 9j Hoffmann-Röder A. Krause N. Org. Biomol. Chem.  2005,  3:  387 
    Google Scholar
  • 9k Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 
    Google Scholar
  • 9l Hashmi ASK. Angew. Chem. Int. Ed.  2005,  44:  6990 
    Google Scholar
  • 9m Ma S. Yu S. Gu Z. Angew. Chem. Int. Ed.  2006,  45:  200 
    Google Scholar
  • 9n Li ZJ. Brouwer C. He C. Chem. Rev.  2008,  108:  3239 
    Google Scholar
  • 9o Patil NT. Yamamoto Y. ARKIVOC  2007,  (v):  6 
    Google Scholar
  • 10a Sun J. Conley MP. Zhang L. Kozmin SA. J. Am. Chem. Soc.  2006,  128:  9705 
    Google Scholar
  • 10b Barluenga J. Dieguez A. Fernandez A. Rodriguez F. Fananas FJ. Angew. Chem. Int. Ed.  2006,  45:  2091 
    Google Scholar
  • 10c Buzas A. Gagosz F. Synlett  2006,  2727 
    Google Scholar
  • 10d Hashmi ASK. Salathe R. Frey W. Synlett  2007,  1763 
    Google Scholar
  • 10e Dube P. Toste DF. J. Am. Chem. Soc.  2006,  128:  12062 
    Google Scholar
  • 10f Hotha S. Kashyap S. J. Am. Chem. Soc.  2006,  128:  9620 
    Google Scholar
  • 10g Gockel B. Krause N. Org. Lett.  2006,  8:  4485 
    Google Scholar
  • 10h Gorin DJ. Davis NR. Toste FD. J. Am. Chem. Soc.  2005,  127:  11260 
    Google Scholar
  • 10i Brouwer C. Rahaman R. He C. Synlett  2007,  1785 
    Google Scholar
  • 10j Nakamura I. Sato T. Yamamoto Y. Angew. Chem. Int. Ed.  2006,  45:  4473 
    Google Scholar
  • 10k Nakamura I. Sato T. Terada M. Yamamoto Y. Org. Lett.  2007,  9:  4081 
    Google Scholar
  • 10l Shapiro ND. Toste FD. J. Am. Chem. Soc.  2008,  130:  9244 
    Google Scholar
  • 10m Hashmi ASK. Frost TM. Bats JW. J. Am. Chem. Soc.  2000,  122:  11553 
    Google Scholar
  • 10n Hashmi ASK. Schwarz L. Choi J.-H. Frost TM. Angew. Chem. Int. Ed.  2000,  39:  2285 ; Angew. Chem. 2000, 112, 2382
    Google Scholar
  • 11a Zhang L. Kozmin SA. J. Am. Chem. Soc.  2005,  127:  6962 
    Google Scholar
  • 11b Leseurre L. Toullec PY. Genet JP. Michelet V. Org. Lett.  2007,  9:  4049 
    Google Scholar
  • 11c Buzas AK. Istrate FM. Gagosz F. Angew. Chem. Int. Ed.  2007,  46:  1141 
    Google Scholar
  • 11d Yang T. Campbell L. Dixon DJ. J. Am. Chem. Soc.  2007,  129:  12070 
    Google Scholar
  • 11e Yao T. Zhang X. Larock RC.
    J. Org. Chem.  2005,  70:  7679 
    Google Scholar
  • 11f Zhang J. Schmalz HG. Angew. Chem. Int. Ed.  2006,  45:  6704 
    Google Scholar
  • 11g Lin CC. Teng TM. Odedra A. Liu RS. J. Am. Chem. Soc.  2007,  129:  3798 
    Google Scholar
  • 11h Belting V. Krause N. Org. Lett.  2006,  8:  4489 
    Google Scholar
  • 12a Fu WJ. Huang X. Li Y. Synlett  2007,  321 
    Google Scholar
  • 12b Huang X. Fu WJ. Tetrahedron Lett.  2008,  49:  2359 
    Google Scholar
  • 12c Fu WJ. Huang X. Tetrahedron Lett.  2008,  49:  562 
    Google Scholar
  • 15a Kamijo S. Sasaki Y. Yamamoto Y. Tetrahedron Lett.  2004,  45:  35 
    Google Scholar
  • 15b Halim R. Scammells PJ. Flynn BL. Org. Lett.  2008,  10:  1967 
    Google Scholar
13

The crystal data of 2a has been deposited in CCDC with number 710261. X-ray data for compound 2a: C44H34N2O2; Mw = 622.73; triclinic; space group: P-1; lattice parameters: a = 10.5127 (12) Å, b = 11.3097 (13) Å, c = 14.1538 (16) Å, α = 85.2950 (10)˚, β = 81.3660 (10)˚, γ = 78.5540 (10)˚, V = 1628.3 (3) ų; D calc = 1.270 g/cm³; F000 = 656; residuals: R; Rw: 0.0578, 0.1065.

14

General Procedure
To a solution of N-(o-alkynylphenyl) imines 1 (0.5 mmol) in dry CH2Cl2 (5 mL) was added a solution of AuCl3 (3 mol%) in MeCN (0.05 M). The mixture was stirred for 30 min at r.t. After evaporation of the solvent, the residue was purified by column chromatography on SiO2 (PE-EtOAc, 25:1) to afford 2.