Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones Catalyzed by p-TSA

REFERENCES

• Yamada , Y. ; Kitajima , M. ; Kogure , N. ; Takayama , H. Four novel gelsedine-type oxindole alkaloids from gelsemium elegans . Tetrahedron 2008 , 64 , 7690 – 7694 .
   Web of Science ®Google Scholar
• Kogure , N. ; Kobayashi , H. ; Ishii , N. ; Kitajima , M. ; Wongseripipatana , S. ; Takayama , H. New humantenine-type indole alkaloids with iridoid unit from gelsemium species . Tetrahedron Lett. 2008 , 49 , 3638 – 3642 .
   Web of Science ®Google Scholar
• Kam , T. S. ; Choo , Y. M. Novel macroline oxindoles from a malayan alstonia . Tetrahedron 2000 , 56 , 6143 – 6150 .
   Web of Science ®Google Scholar
• Wu , Y.-Q. ; Kitajima , M. ; Kogure , N. ; Zhang , R. ; Takayama , H. Two novel indole alkaloids, kopsiyunnanines A and B, from a yunnan kopsia . Tetrahedron Lett. 2008 , 49 , 5935 – 5938 .
   Web of Science ®Google Scholar
• Bolotov , V. V. ; Drugovina , V. V. ; Yakovleva , L. V. ; Bereznyakova , A. I. Synthesis and biological activity of 1-aminomethyl-3,3-diaryl-2-oxoindolines . Khim. Farm. Zh. 1982 , 16 , 58 – 61 .
   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
• Marti , C. ; Carreira , E. M. Construction of spiro[pyrrolidine-3,3′-oxindoles]: Recent applications to the synthesis of oxindole alkaloids . Eur. J. Org. Chem. 2003 , 63 , 2209 – 2219 .
   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
• Klumpp , D. 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
• Jursic , B. ; Stevens , E. D. Preparation of dibarbiturates of oxindole by condensation of isatin and barbituric acid derivatives . Tetrahedron Lett. 2002 , 43 , 5681 – 5683 .
   Web of Science ®Google Scholar
• Rad-Moghadam , K. ; Sharifi-Kiasaraie , M. ; Taheri-Amlashi , H. Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids. Tetrahedron 2010, 66, 2316–2321.
   PubMed Web of Science ®Google Scholar
• Karimi , N. O. ; Hooesina , H. ; Majid , S. ; Minaa , Z. ; Masoumeh , Z. ; Tavakoli , N. On water: Brønsted acidic ionic liquid [(CH2)4SO3HMIM][HSO4]–catalyzed synthesis of oxindole derivatives . Chin. J. Chem. 2011 , 29 , 321 – 323 .
   Web of Science ®Google Scholar
• Kamal , A. , Srikanth , Y. V. V. , Khan , N. A. , Shaik , T. B. , Ashraf , M. Synthesis of 3,3-diindolyl oxyindoles efficiently catalyzed by FeCl3 and their in vitro evaluation for anticancer activity . Bioorg. Med. Chem. Lett. 2010 , 20 , 5229 – 5231 .
   PubMed Web of Science ®Google Scholar
• Ji , S.-J. ; Wang , S.-Y. 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
• Yadav , J. S. ; Reddy , B. V. S. ; Gayathri , K. U. ; Meraj , S. ; Prasad , A. R. Bismuth(III) triflate–catalyzed condensation of isatin with indoles and pyrroles: A facile synthesis of 3,3-diindolyl and 3,3-dipyrrolyloxindoles . Synthesis 2006 , 24 , 4121 – 4123 .
   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
• Paira , P. ; Hazra , A. ; Kumar , S. ; Paira , R. ; Sahu , K. B. ; Naskar , S. ; Saha , P. ; Mondal , S. ; Maity , A. ; Banerjee , S. ; Mondal , N. B. Efficient synthesis of 3,3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential . Bioorg. Med. Chem. Lett. 2009 , 19 , 4786 – 4789 .
   PubMed Web of Science ®Google Scholar
• Reddy , B. V. S. ; Rajeswari , N. ; Sarangapani , M. ; Prashanthi , Y. ; Ganji , R. J. ; Addlagatta , A. Iodine-catalyzed condensation of isatin with indoles: A facile synthesis of di(indolyl)indoline-2-ones and evaluation of their cytotoxicity . Bioorg. Med. Chem. Lett. 2012 , 22 , 2460 – 2463 .
   PubMed Web of Science ®Google Scholar
• Praveen , C. ; Ayyanar , A. ; Perumal , P. T. Practical synthesis, anticonvulsant, and antimicrobialactivity of N-allyl and N-propargyl di(indolyl)indolin-2-ones . Bioorg. Med. Chem. Lett. 2011 , 21 , 4072 – 4077 .
   PubMed Web of Science ®Google Scholar
• Azizian , J. ; Mohammadi , A. A. ; Karimi , A. R. ; Mohammadizadeh , M. R. KAl(SO4)2 · 12H2O as a recyclable Lewis acid catalyst for synthesis of some new oxindoles in aqueous media . J. Chem. Res. Synop. 2004 , 6 , 424 – 426 .
   Google Scholar
• Gaudemer , F. ; Gaudemer , A. Oxidation of allyl and allenylcobaloximes by manganese(III) acetate: A new route to dimethylglyoxime monoethers . Tetrahedron Lett. 1980 , 36 , 1445 – 1447 .
   Web of Science ®Google Scholar
• Tabatabaeian , K. ; Mamaghani , M. ; Mahmoodi , N. ; Khorshidi , A. Ruthenium-catalyzed efficient routes to oxindole derivatives . Can. J. Chem. 2009 , 87 , 1213 – 1217 .
   Web of Science ®Google Scholar
• Subhendu , N. ; Pritam , S. ; Rupankar , P. ; Priyankar , P. ; Abhijit , H. ; Krishnendu , S. B. ; Sukdeb , B. ; Nirup , M. B. Aqueous phase supramolecular synthesis of 3,2- and 3,3-dihetero-aromatic oxindoles catalysed by β-cyclodextrin . J. Chem. Res. 2009 , 3 , 174 – 177 .
   Google Scholar
• Parasa , H. ; Saikat , D. S. ; Dilip , K. Efficient synthesis of bis- and tris-indolylalkanes catalyzed by a Brønsted acid–surfactant catalyst in water . Synth. Commun. 2008 , 38 , 2870 – 2880 .
   Web of Science ®Google Scholar
• Gibbs , T. J. K. ; Tomkinson , N. C. O. Aminocatalytic preparation of bisindolylalkanes . Org. Biomol. Chem. 2005 , 22 , 4043 – 4045 .
   Web of Science ®Google Scholar
• Alimohammadi , K. ; Sarrafi , Y. ; Tajbakhsh , M. H6P2W18O62: A green and reusable catalyst for the synthesis of 3,3-diaryloxindole derivatives in water . Monatsh. Chem. 2008 , 139 , 1037 – 1039 .
   Web of Science ®Google Scholar
• Nikpassand , M. ; Mamaghani , M. ; Tabatabaeian , K. ; Samimi , H. A. An efficient and clean synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones using KSF . Synth. Commun. 2010 , 40 , 3552 – 3560 .
   Web of Science ®Google Scholar
• Jadidi , K. ; Ghahremanzadeh , R. ; Bazgir , A. Efficient synthesis of spiro[chromeno[2,3-d]pyri-midine-5,3′-indoline]tetraones by a one-pot and three-component reaction. J. Comb. Chem. 2009, 11, 341–344.
   PubMed Web of Science ®Google Scholar
• Ghahremanzadeh , R. ; Shakibaei , G. I. ; Ahadi , S. ; Bazgir , A. One-pot, pseudo-four-component synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-trione library . J. Comb. Chem. 2010 , 12 , 191 – 194 .
   PubMed Web of Science ®Google Scholar
• Liu , T.-Y. ; Cui , H.-L. ; Zhang , Y. ; Jiang , K. ; Du , W. ; He , Z.-Q. ; Chen , Y.-C. Organocatalytic and highly enantioselective direct ramination of aromatic ketones . Org. Lett. 2007 , 9 , 3671 – 3674 .
   PubMed Web of Science ®Google Scholar
• Guo , L.-F. An efficient synthesis of 2,2-bis(1H-indol-3-yl)-2H-acenaphthen-1-one catalyzed by recyclable solid super acid /TiO2 under grinding condition . Chin. Chem. Lett. 2010 , 21 , 1057 – 1061 .
   Web of Science ®Google Scholar