Silica Sulfuric Acid–Catalyzed Friedel–Crafts Alkylation of Indoles with Nitro Olefins

References

• Sundberg , R. J. 1996 . The Chemistry of Indoles 113 New York : Academic Press .
   Google Scholar
• Moore , R. E. , Cheuk , C. , Yang , X. Q. , Patterson , G. M. I. , Bonjouklian , R. , Smika , T. A. , Mynderse , J. , Foster , R. S. , Jones , N. D. , Skiartzendruber , J. K. and Deeter , J. B. 1987 . Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte Hapalosiphon fontinalis . J. Org. Chem. , 52 : 1036
   Web of Science ®Google Scholar
• Garnick , R. L. , Levery , S. B. and LeQuesne , U. P. 1978 . Addition and annulation reactions between indoles and α,β‐unsaturated ketones . J. Org. Chem. , 43 : 1226
   Web of Science ®Google Scholar
• Leonard , J. 1994 . Control of asymmetry through conjugate addition reactions . Contemp. Org. Synth. , 1 : 387
   Google Scholar
• Rossiter , B. E. and Swingle , N. M. 1992 . Asymmetric conjugate addition . Chem. Rev. , 92 : 771
   Web of Science ®Google Scholar
• Ono , N. 2001 . “ The nitro group of organic synthesis ” . In The Nitro Group of Organic Synthesis New York : Wiley‐VCH .
   Google Scholar
• Seebach , D. , Colvin , E. W. , Lehr , F. and Weller , T. 1979 . Nitroaliphatic compounds‐ ideal intermediates in organic synthesis . Chimia , 33 : 1
   Web of Science ®Google Scholar
• Calderari , G. and Seebach , D. 1985 . Asymmetrische Michael‐additionen. Stereoselektive alkylierung chiraler, nicht racemischer enolate durch nitroolefine. Herstellung enantiomerenrein γ‐aminobuttersäure‐ und bernsteinsäure‐derivate . Helv. Chim. Acta , 68 : 1592
   Google Scholar
• Berner , O. M. , Dedeschi , L. and Enders , D. 2002 . Asymmetric Michael additions to nitroalkenes . Eur. J. Org. Chem. , : 1877
   Google Scholar
• Zhou , J. , Ye , M. C. , Huang , Z. Z. and Tang , Y. 2004 . Controllable enantioselective Friedel‐Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo‐C 3‐symmetric trisoxazoline copper(II) complexes . J. Org. Chem. , 69 : 1309
   PubMed Web of Science ®Google Scholar
• Evans , D. A. , Scheidt , K. A. , Fandrick , K. R. , Lann , H. W. and Wu , J. 2003 . Enantioselective indole Friedel‐Crafts alkylations catalyzed by bis(oxazolinyl)pyridine‐scandium(III) triflate complexes . J. Am. Chem. Soc. , 125 : 10780
   PubMed Web of Science ®Google Scholar
• Bandini , M. , Fagioli , M. , Melchiorre , P. , Melloni , A. and Umani‐Ronchi , A. 2003 . Catalytic enantioselective conjugate addition of indoles to simple α,β‐unsaturated ketones . Tetrahedron Lett. , 44 : 5843
   Web of Science ®Google Scholar
• Bandini , M. , Cozzi , P. G. , Giacomini , M. , Melchiorre , P. , Selva , S. and Umani-Ronchi , A. 2002 . Sequential one‐pot InBr3‐catalyzed 1,4‐ then 1,2‐nucleophilic addition to enones . J. Org. Chem. , 67 : 3700
   PubMed Web of Science ®Google Scholar
• Zolfigol , M. A. , Mohammadpoor‐Baltork , I. , Mirjalil , B. F. and Bamoniri , A. 2003 . Silica sulfuric acid: an efficient catalyst for the direct conversion of primary and secondary trimethylsilyl ethers to their corresponding ethers under mild and heterogeneous conditions . Synlett , : 1877
   Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Bodaghi Fard , M. A. 2003 . Silica sulfuric acid: an efficient and reusable catalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones . Tetrahedron Lett. , 44 : 2889
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Boghban Zadeh , M. 2005 . Novel method for the one‐pot three‐component synthesis of 2,3‐dihydroquinazolin‐4(1h)‐ones . Synlett , : 1155
   Google Scholar
• Zolfigol , M. A. and Abdolhamid , B. 2002 . Silica sulfuric acid/NaNo2 as a novel heterogeneous system for the chemoselective N‐nitrosation of secondary amines under mild conditions . Synlett , : 1621
   Google Scholar
• Zolfigol , M. A. , Shirini , F. , Ghorbanichoghawarani , A. and Mohammadpoor-Baltork , I. 2002 . Silica modified sulfuric acid/NaNO2 as a novel heterogeneous system for the oxidation of 1,4‐dihydropyridines under mild conditions . Green. Chem. , 4 : 562
   Web of Science ®Google Scholar
• Hari , G. S. , Nagaraju , M. and Murthy , M. M. 2007 . Solvent‐free one‐pot synthesis of amidoalkyl naphthols catalyzed by silica sulfuric acid . Helv. Chimica. Acta. , 8 : 1497
   Google Scholar
• Riego , J. M. , Sedin , Z. , Zaldivar , J. M. , Marziano , N. C. and Tortato , C. 1996 . Sulfuric acid on silica‐gel: an inexpensive catalyst for aromatic nitration . Tetrahedron Lett. , 37 : 513
   Web of Science ®Google Scholar
• Zolfigol , M. A. 2001 . Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions . Tetrahedron , 57 : 9509
   Web of Science ®Google Scholar
• Noland , W. E. , Christensen , G. M. , Sauer , G. L. and Dutton , G. G. S. 1995 . The reaction of nitroölefins with indole . J. Am. Chem. Soc. , 77 : 456
   Google Scholar
• Iqbal , Z. , Jackson , A. H. and Rao , K. R. N. 1988 . Reactions on solid supports part IV: Reactions of αβ‐unsaturated carbonyl compounds with indoles using clay as catalyst . Tetrahedron Lett. , 29 : 2577
   Web of Science ®Google Scholar