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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 15
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Original Articles

Unexpected Synthesis of Highly Substituted Indole Derivatives

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Pages 2232-2240 | Received 25 Apr 2009, Published online: 06 Jul 2010

REFERENCES

  • (a) Saxton , J. E. Indoles ; Wiley-Interscience : New York , 1983 ; part 4; (b) Saxton, J. E. Recent progress in the chemistry of indole alkaloids and mould metabolites. Nat. Prod. Rep. 1994, 493; Saxton, J. E. Recent progress in the chemistry of the monoterpenoid indole alkaloids. Nat. Prod. Rep. 1995, 387; (c) Ihara, M.; Fukumoto, K. Recent progress in the chemistry of non-monoterpenoid indole alkaloids. Nat. Prod. Rep. 1995, 277.
  • (a) Sundberg , R. J. Indoles ; Academic Press : San Diego , 1996; (b) Chen, C. Y.; Liberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Synthesis of indoles via a palladium-catalyzed annulation between iodoanilines and ketones. J. Org. Chem. 1997, 62, 2676.
  • (a) Robinson , B. The Fischer Indole Synthesis ; Wiley-Interscience : New York , 1982 ; (b) Hughes, D. L. A convergent approach to 2-substituted-5-methoxyindoles: Application to the synthesis of melatonin. Org. Prep. Proc. Int. 1993, 25, 607; (c) Gribble, G. W. Recent developments in indole ring synthesis: Methodology and applications. Contemp. Org. Synth. 1994, 1, 145, and references cited therein .
  • (a) Odle , R. ; Blevins , B. ; Ratcliff , M. ; Hegedus , L. S. Conversion of 2-halo-N-allylanilines to indoles via palladium(0)oxidative addition–insertion reactions . J. Org. Chem. 1980 , 45 , 2709 ; (b) Larock , R. C. ; Babu , S. Synthesis of nitrogen heterocycles via palladium-catalyzed intramolecular cyclization . Tetrahedron Lett. 1987 , 28 , 5291 ; (c) Larock , R. C. ; Yum , E. K. Synthesis of indoles via palladium-catalyzed hetero-annulation of internal alkynes . J. Am. Chem. Soc. 1991 , 113 , 6689 .
  • (a) Iida , H. ; Yuasa , Y. ; Kibayashi , C. Intramolecular cyclization of enaminones involving arylpalladium complexes: Synthesis of carbazoles . J. Org. Chem. 1980 , 45 , 2938 – 2942 ; (b) Sakamoto , T. ; Nagano , T. ; Kondo , Y. ; Yamanake , H. Condensed heteroaromatic ring systems, XVII: Palladium-catalyzed cyclization of β-(2-halophenyl)amino substituted α,β-unsaturated ketones and esters to 2,3-disubstituted indoles . Synthesis 1990 , 215 .
  • Wagaw , S. ; Yang , B. Y. ; Buchwald , S. L. A palladium-catalyzed method for the preparation of indoles via the Fischer indole synthesis . J. Am. Chem. Soc. 1999 , 121 , 10251 .
  • (a) Gribble , G. W. Recent developments in indole ring synthesis: Methodology and applications . J. Chem. Soc., Perkin Trans. 1 2000 , 1045 ; (b) Rutherford , J. L. ; Rainka , M. P. ; Buchwald , S. L. An annulative approach to highly substituted indoles: Unusual effect of phenolic additives on the success of the arylation of ketone enolates . J. Am. Chem. Soc. 2002 , 124 , 15168 ; (c) Arisawa , M. ; Terada , Y. ; Nakagawa , M. ; Nishida , A. Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis . Angew. Chem., Int. Ed. 2002 , 41 , 4732 ; (d) Smith , A. B. ; Kanoh , N. ; Ishiyama , H. ; Minakawa , N. ; Rainier , J. D. ; Hartz , R. A. ; Cho , Y. S. ; Cui , H. ; Moser , W. H. Tremorgenic indole alkaloids: The total synthesis of (–)-penitrem D . J. Am. Chem. Soc. 2003 , 125 , 8228 ; (e) Shimada , T. ; Nakamura , I. ; Yamamoto , Y. Intramolecular C‒N bond addition of amides to alkynes using platinum catalyst . J. Am. Chem. Soc. 2004 , 126 , 10546 ; (f) Willis , M. C. ; Brace , G. N. ; Holmes , I. P. Palladium-catalyzed tandem alkenyl and aryl C—N bond formation: A cascade N-annulation route to 1-functionalized indoles . Angew. Chem., Int. Ed. 2005 , 44 , 403 ; (g) Baran , P. S. ; Guerrero , C. A. ; Ambhaikar , N. B. ; Hafensteiner , B. D. Short, enantioselective total synthesis of stephacidin A . Angew. Chem., Int. Ed. 2005 , 44 , 606 .
  • (a) Padwa , A. ; Smolanoff , J. ; Tremper , A. Photochemical transformations of small ring heterocyclic compounds, 71: Intramolecular reorganization of some unsaturated 2H-azirines . J. Org. Chem. 1976 , 41 , 543 ; (b) Russell , G. A. ; Yao , C.-F. ; Tashtoush , H. I. ; Russell , J. E. ; Dedolph , D. F. Addition, substitution, and deoxygenation reactions of alpha-phenyl-beta-nitrostyrenes with the anions of thiols and diethyl phosphite: Formation of indoles by reaction with ethyl phosphates . J. Org. Chem. 1991 , 56 , 663 .
  • Rajeshwar , R. S. ; Himabindu , V. ; Pratap , R. P. ; Mahesh , R. G. An efficient synthesis of highly substituted pyrrole and bispyrrole derivatives . J. Heterocycl. Chem. 2007 , 44 , 923 – 926 .

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