An Efficient and Clean Synthesis of Symmetrical and Unsymmetrical 3,3-Di(indolyl)Indolin-2-ones Using KSF

REFERENCES

• Sundberg , R. J. The Chemistry of Indoles ; Academic Press : New York , 1996 .
   Google Scholar
• Wang , S.-Y. ; Ji , S.-J. Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation . Tetrahedron 2006 , 62 , 1527 – 1535 .
   Web of Science ®Google Scholar
• Lo , K. K. W. ; Tsang , K. H. K. ; Hui , W. K. ; Zhu , N. Luminescent rhenium(I) diimine indole conjugates—photophysical, electrochemical and protein-binding properties . Chem. Commun. 2003 , 2704 – 2705 .
   PubMed Web of Science ®Google Scholar
• Ramirez , A. ; Garcia-Rubio , S. Current progress in the chemistry and pharmacology of akuammiline alkaloids . Curr. Med. Chem. 2003 , 10 , 1891 – 1915 .
   PubMed Web of Science ®Google Scholar
• Mi , X. ; He , S. ; Luo , J. ; Cheng , J.-P. Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines . Tetrahedron Lett. 2004 , 45 , 4567 – 4570 .
   Web of Science ®Google Scholar
• Pajouhesh , H. ; Parsons , R. ; Popp , F. D. Potential anticonvulsants VI: Condensation of isatins with cyclohexanone and other cyclic ketones. J. Pharm. Sci. 1983, 72, 318–321.
   PubMed Web of Science ®Google Scholar
• Joshi , K. C. ; Pathak , V. N. ; Jain , S. K. Studies of potential organo-fluorine antibacterial agents. Part 5: Synthesis and antibacterial activity of some new fluorine-containing indole-2,3-dione derivatives . Pharmazie 1980 , 35 , 677 – 679 .
   PubMed Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Chandrakanth , D. ; Satheesh , G. The first example of the C-3 alkylation of indoles with cyclopropyl ketones promoted by CeCl3 · 7H2O/LiI . Tetrahedron Lett. 2007 , 48 , 8040 – 8042 .
   Web of Science ®Google Scholar
• Humphrey , G. R. ; Kuethe , J. T. Practical methodologies for the synthesis of indoles . Chem. Rev. 2006 , 106 , 2875 – 2911 .
   PubMed Web of Science ®Google Scholar
• Moore , R. E. ; Cheuk , C. ; Yang , X. Q. ; Patterson , G. M. L. ; Bonjouklian , R. , Smita , T. A. ; Mynderse , J. ; Foster , R. S. , Jones , N. D. ; Skiartzendruber , J. K. ; Deeter , J. B. Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte Hapalosiphon fontinalis . J. Org. Chem. 1987 , 52 , 1036 – 1043 .
   Web of Science ®Google Scholar
• Garnick , R. L. ; Levery , S. B. ; LeQuesne , U. P. Addition and annulation reactions between indoles and alpha, beta-unsaturated ketones . J. Org. Chem. 1987 , 43 , 1226 – 1229 .
   Web of Science ®Google Scholar
• Moore , R. E. ; Cheuk , C. ; Patterson , G. M. L. Hapalindoles: New alkaloids from the blue-green alga Hapalosiphon fontinalis . J. Am. Chem. Soc. 1984 , 106 , 6456 – 6457 .
   Web of Science ®Google Scholar
• Szmuszkovicz , J. The reaction of substituted indoles with methyl vinyl ketone. New synthesis of 2-methylcarbazole . J. Am. Chem. Soc. 1957 , 79 , 2819 – 2821 .
   Web of Science ®Google Scholar
• Roomi , M. ; Macdonald , S. F. Reductive C-alkylation. II . Can. J. Chem. 1970 , 48 , 139 – 143 .
   Web of Science ®Google Scholar
• Bandini , M. ; Cozzi , P. G. ; Giacomini , M. ; Melchiorre , P. ; Selva , S. ; Umani-Ronchi , A. Sequential one-pot InBr3-catalyzed 1,4- then 1,2-nucleophilic addition to enones . J. Org. Chem. 2002 , 67 , 3700 – 3704 .
   PubMed Web of Science ®Google Scholar
• Harrington , P. E. ; Kerr , M. A. Reaction of indoles with electron deficient olefins catalyzed by Yb(OTf)3 · 3H2O . Synlett . 1996 , 1047 – 1050 .
   Web of Science ®Google Scholar
• Chatterjee , A. ; Manna , S. ; Banerji , J. ; Pascard , C. ; Prange , T. ; Shoolery , J. N. Lewis-acid-induced electrophilic substitution in indoles with acetone, part 2 . J. Chem. Soc., Perkin Trans. I 1980 , 553 – 555 .
   Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Jafari , A. A. Aluminumdodecatungstophosphate (AlPW12O40), a versatile and a highly water tolerant green Lewis acid catalyzes efficient preparation of indole derivatives . J. Mol. Catal. A, Chemical 2006 , 244 , 168 – 172 .
   Web of Science ®Google Scholar
• Banerji , J. ; Dutta , U. ; Basak , B. ; Saha , M. ; Budzikiewicz , H. ; Chatterjee , A. Electrophilic substitution reactions of indole: Part XX—Use of montmorillonite clay K-10 . Indian J. Chem. B 2001 , 40 ( 10 ), 981 – 984 .
   Google Scholar
• Bergman , J. ; Eklund , N. Synthesis and studies of tris-indolobenzenes and related compounds . Tetrahadron 1980 , 36 , 1445 – 1450 .
   Web of Science ®Google Scholar
• Azizian , J. ; Mohammadi , A. A. ; Karimi , N. ; Mohammadizadeh , M. R. ; Karimi , A. R. Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives . Catal. Commun. 2006 , 7 , 752 – 755 .
   Web of Science ®Google Scholar
• Hewawasam , P. ; Gribkoff , V. K. ; Pendri , Y. ; Dworetzky , S. I. ; Meanwell , N. A. ; Martinez , E. ; Boissard , C. G. ; Post-Munson , D. J. ; Trojnacki , J. T. ; Yeleswaram , K. ; Pajor , L. M. ; Knipe , J. ; Gao , Q. ; Perrone , R. ; Starrett , J. E. The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels . J. Bioorg. Med. Chem. Lett. 2002 , 12 , 1023 – 1030 .
   PubMed Web of Science ®Google Scholar
• Nicolaou , K. C. ; Bella , M. ; Chen , D. Y. K. ; Huang , X. ; Ling , T. ; Snyder , S. A. Total synthesis of diazonamide A . Angew. Chem., Int. Ed. 2002 , 41 , 3495 – 3499 .
   PubMed Web of Science ®Google Scholar
• Klumpp , A. A. ; Yeung , K. Y. ; Prakash , G. K. S. ; Olah , G. A. Preparation of 3,3-diaryloxindoles by superacid-induced condensations of isatins and aromatics with a combinatorial approach . J. Org. Chem. 1998 , 63 , 4481 – 4484 .
   Web of Science ®Google Scholar
• Narender , N. ; Srinivasu , P. ; Kulkarni , S. J. ; Raghavan , K. V. Liquid phase acylation of amines with acetic acid over HY zeolite. Green Chem. 2000, 2, 104–105.
   Web of Science ®Google Scholar
• Balogh , M. ; Laszlo , P. Organic Chemistry Using Clay ; Springer Verlag : New York , 1993 .
   Google Scholar
• Nikpassand , M. ; Mamaghani , M. ; Tabatabaeian , K. An efficient one-pot three-component synthesis of fused 1,4-dihydropyridines using HY-zeolite . Molecules 2009 , 14 , 1468 – 1474 .
   PubMed Web of Science ®Google Scholar
• Samimi , H. A. ; Mamaghani , M. ; Tabatabaeian , K. A convenient one-pot three component approach to synthesis of highly substituted iminothiazolines . Heterocycles 2008 , 75 , 2825 – 2833 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. ; Khorshidi , A. Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles . Tetrahedron Lett. 2008 , 49 , 1450 – 1454 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. ; Khorshidi , A. RuIII-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones . J. Mol. Catal. A 2007 , 270 , 112 – 116 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. ; Khorshidi , A. Efficient RuIII-catalyzed condensation of indoles and aldehydes or ketones . Can. J. Chem. 2006 , 84 , 1541 – 1545 .
   Web of Science ®Google Scholar