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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
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Original Articles

Silica Gel, an Effective Catalyst for the Reaction of Electron-Deficient Nitro-Olefins with Nitrogen Heterocycles

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Pages 2935-2940 | Received 23 Jul 2009, Published online: 25 Aug 2010

REFERENCES

  • (a) Thomas , L. G. In Heterocyclic Chemistry; , 3rd ed .; Longman : England , 1997 ; parts 1, 2, and 5 ; (b) Sundberg , R. D. Pyrroles and their benzo derivatives, synthesis and applications . In Comprehensive Heterocyclic Chemistry ; A. R. Katrizky , C. W. Ress (Eds.) ; Pergamon : Oxford , 1984 ; vol. 4 , pp. 313 – 376 ; (c) Saxton, J. E. Recent progress in the chemistry of the monoterpenoid indole alkaloids. Nat. Prod. Rep. 1997, 14, 559; (d) Toyota, M.; Ihara, N. Recent progress in the chemistry of non-monoterpenoid indole alkaloids. Nat. Prod. Rep. 1998, 15, 327; (e) Leonid, I.; Belen, K. Relative stabilities of hetarenium ions: Factors controlling positional selectivities of electrophilic substitution and acid-induced transformations of pyrrole, furan, and thiophene derivatives. Heterocycles 1994, 37, 2029; (f) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1969; p. 113.
  • Yadav , J. S. ; Abraham , S. ; Reddy , B. V. S. ; Sabitha , G. InCl3-catalysed conjugate addition of indoles with electron-deficient olefiens . Synthesis. 2001 , 2165 – 2169 .
  • Zhan , Z.-P. ; Yu , J.-L. ; Yang , W.-Z. Bismuth trichloride–catalyzed C-alkylation of pyrroles with electron-deficient olefins . Synth. Commun. 2006 , 36 , 1373 – 1382 .
  • Lin , C. ; Hsu , J. ; Sastry , M. N. V. ; Fang , H. ; Tu , Z. ; Liu , J.-T. ; Ching-Fa , Y. I2-catalyzed Michael addition of indole and pyrrole to nitroolefins . Tetrahedron. 2005 , 61 , 11751 – 11757 .
  • An , L.-T. ; Zou , J.-P. ; Zhang , L.-L. ; Zhang , Y. Sulfamic acid–catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition. Tetrahedron Lett. 2007, 48, 4297–4300.
  • Firouzabadi , H. ; Iranpoor , N. ; Nowrouzi , F. The facile and efficient Michael addition of indoles and pyrrole to α,β-unsaturated electron-deficient compounds catalyzed by aluminum dodecyl sulfate trihydrate [Al(DS)3]·3H2O in water . Chem. Commun. 2005 , 789 – 791 .
  • Harrington , P. E. ; Kerr , M. A. Reaction of indoles with electron deficient olefins catalyzed by Yb(OTf)3·3H2O . Synlett. 1996 , 1047 – 1050 .
  • Bartoli , G. ; Bosco , M. ; Giuli , S. ; Giuliani , A. ; Lucarelli , L. ; Marcantoni , E. ; Sambri , L. ; Torregiani , E. Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors: New practical linear approach to alkyl 9H-β-carboline-4-carboxylate . J. Org. Chem. 2005 , 70 , 1941 – 1944 .
  • (a) Zhan , Z-P. ; Yang , W-Z. ; Yang , R-F. ; Microwave-assisted addition of pyrroles to electron-deficient olefins: A rapid entry to C-alkyl pyrroles . Synlett. 2005 , 16 , 2425 – 2428 ; (b) Kusurkar , R. S. ; Alkobati , N. A. H. ; Gokule , A. S. ; Chaudhari , P. M. ; Waghchaure , P. B. Thermal and microwave-assisted conjugate additions of indole on electron-deficient nitro-olefins . Synth. Commun. 2006 , 36 , 1075 – 1081 .
  • (a) Coma , A. Inorganic solid acids and their use in acid-catalyzed hydrocarbon reactions . Chem. Rev. 1995 , 95 , 559 – 614 ; (b) Isobe , K. Cubane-type clusters as potential models for inorganic solid surface Biginelli reactions . Acc. Chem. Res. 1993 , 26 , 524 – 529 .
  • (a) Kamitori , Y. ; Hojo , M. ; Masuda , R. ; Izumi , T. ; Tsukamoto , S. Silica gel as an effective catalyst for the alkylation of phenols and some heterocyclic aromatic compounds . J. Org. Chem. 1984 , 49 , 4161 – 4165 ; (b) Kotsuki , H. ; Hayashida , K. ; Shimanouchi , T. ; Nishizawa , H. High-pressure organic chemistry, 19: High-pressure-promoted, silica gel–catalyzed reaction of epoxides with nitrogen heterocycles . J. Org. Chem. 1996 , 61 , 984 – 990 ; (c) Chavan , F. ; Madje , B. ; Bharad , J. ; Ubale , M. ; Ware , M. ; Shingare , M. ; Shinde , N. Silica gel–supported NaHSO4-catalyzed organic reaction: An efficient synthesis of coumarins . Bull. Catal. Soc. Ind. 2008 , 7 , 41 – 45 .

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