Montmorillonite K10: Catalyst for Friedel–Crafts Alkylation of Indoles and Pyrrole with Nitroalkenes Under Solventless Conditions

REFERENCES

• Trost , B. M. On inventing reactions for atom economy . Acc. Chem. Res. 2002 , 35 , 695 – 705 .
   PubMed Web of Science ®Google Scholar
• Ono , N. The Nitro Group in Organic Synthesis ; Wiley-VCH : New York , 2001 .
   Google Scholar
• Berner , O. M. ; Tedeschi , L. ; Enders , D. Asymmetric Michael additions to nitroalkenes. Eur. J. Org. Chem. 2002, 1877–1894.
   Google Scholar
• Sundberg , R. J. The Chemistry of Indoles ; Academic Press : New York , 1996 .
   Google Scholar
• Harada , H. ; Hirokawa , Y. ; Suzuki , K. ; Hiyama , Y. ; Oue , M. ; Kawashima , H. ; Kato , H. ; Yoshida , N. ; Furutani , Y. ; Kato , S. Chem. Pharm. Bull. 2005 , 53 , 184 – 198 .
   PubMed Web of Science ®Google Scholar
• (a) Herrera , R. P. ; Sgarzani , V. ; Bernardi , L. ; Ricci , A. Catalytic enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst . Angew. Chem. Int. Ed. 2005 , 44 , 6576 – 6579 ; (b) Bartoli , G. ; Antonio , G. D. ; Giuli , S. ; Marcantoni , E. ; Marcolini , M. ; Paoletti , M. The CeCl3·7H2O/NaI/SiO2 system as an efficient promoter for the Friedel–Crafts reaction of indoles to nitroalkenes under solvent-free conditions . Synthesis 2008 , 320 – 324 .
   PubMed Web of Science ®Google Scholar
• Alam , M. M. ; Varala , R. ; Adapa , S. R. Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 . Tetrahedron Lett. 2003 , 44 , 5115 – 5119 .
   Web of Science ®Google Scholar
• Lin , C. C. ; Hsu , J. M. ; Sastry , M. N. V. ; Fang , H. L. ; Tu , Z. J. ; Liu , J. T. ; Yao , C. F. I2-catalyzed Michael addition of indole and pyrrole to nitroolefins . Tetrahedron 2005 , 61 , 11751 – 11757 .
   Web of Science ®Google Scholar
• Zhan , Z. P. ; Yang , R. F. ; Lang , K. Samarium triiodide–catalyzed conjugate addition of indoles with electron-deficient olefins . Tetrahedron Lett. 2005 , 46 , 3859 – 3862 .
   Web of Science ®Google Scholar
• 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-beta-carboline-4-carboxylate . J. Org. Chem. 2005 , 70 , 1941 – 1944 .
   PubMed Web of Science ®Google Scholar
• Azizi , N. ; Arynasab , F. ; Saidi , M. R. Efficient Friedel–Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water . Org. Biomol. Chem. 2006 , 4 , 4275 – 4277 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Ballini , R. ; Clemente , R. R. ; Palmieri , A. ; Petrini , M. Conjugate addition of indoles to nitroalkenes promoted by basic alumina in solventless conditions . Adv. Synth. Catal. 2006 , 348 , 191 – 196 .
   Google Scholar
• Clark , J. H. ; Rhodes , C. N. Clean synthesis using porous inorganic solid catalysts and supported reagents, , 1st ed. ; Royal Society of Chemistry : Cambridge , UK , 2000 .
   Google Scholar
• Dintzner , M. R. ; Little , A. J. ; Pacilli , M. ; Pileggi , D. J. ; Osner , Z. R. ; Lyons , T. W. Montmorillonite clay–catalyzed hetero-Diels–Alder reaction of 2,3-dimethyl-1,3-butadiene with benzaldehydes . Tetrahedron Lett. 2007 , 48 , 1577 – 1579 .
   Web of Science ®Google Scholar
• Abid , M. ; Spaeth , A. ; Torok , B. Solvent-free solid acid-catalyzed electrophilic annelations: A new green approach for the synthesis of substituted five-membered N-heterocycles . Adv. Synth. Catal. 2006 , 348 , 2191 – 2196 .
   Web of Science ®Google Scholar
• Varma , R. S. Clay and clay-supported reagents in organic synthesis . Tetrahedron 2002 , 58 , 1235 – 1255 .
   Web of Science ®Google Scholar
• An , L. T. ; Ding , F. Q. ; Zou , J. P. ; Lu , X. H. Montmorillonite K10: An efficient catalyst for solvent-free synthesis of 1,5-benzodiazepine derivatives . Synth. Commun. 2008 , 38 , 1259 – 1267 .
   Web of Science ®Google Scholar
• Gilchrist , T. L. Heterocyclic Chemistry, , 3rd ed. ; Addison Wesley Longman : London , 1997 .
   Google Scholar
• Joule , J. A. ; Mills , K. Heterocyclic Chemistry, , 4th ed. ; Blackwell Science Ltd. : Oxford , 2000 .
   Google Scholar
• Eicher , T. ; Hauptmann , S. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, , 2nd ed. ; Wiley-VCH : Weinheim , 2003 .
   Google Scholar