Triton B–Assisted, Efficient, and Convenient Synthesis of 3-Indolyl-3-hydroxy Oxindoles in Aqueous Medium

REFERENCES

• Sundberg , R. J. The Chemistry of Indoles ; Academic Press : New York , 1996 ; 113 .
   Google Scholar
• Garden , S. J. ; Torres , J. C. ; Ferreira , A. A. ; Silva , R. B. ; Pinto , A. C. A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A . Tetrahedron Lett. 1997 , 38 , 1501 .
   Web of Science ®Google Scholar
• Pajouhesh , H. ; Parsons , R. ; Popp , F. D. Potential anticonvulsants VI: Condensation of isatin with cyclohexanone and other cyclic ketones . J. Pharm. Sci. 1983 , 72 , 318A .
   PubMed Web of Science ®Google Scholar
• Tokunaga , T. ; Hume , W. E. ; Nagamine , J. ; Kawamura , T. ; Taiji , M. ; Nagata , R. Structure–activity relationships of the oxindole growth hormone secretagogues . Bioorg. Med. Chem. Lett. 2005 , 15 , 1789 .
   PubMed Web of Science ®Google Scholar
• Yong , S. R. ; Ung , A. T. ; Pyne , S. G. ; Skelton , B. W. ; White , A. H. Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities . Tetrahedron 2007 , 63 , 5579 .
   Web of Science ®Google Scholar
• Berensa , U. ; Brown , J. M. ; Long , J. ; Seike , R. Synthesis and resolution of 2,2′-bis-diphenylphosphino [3,3′] biindolyl: A new atropisomeric ligand for transition metal catalysis . Tetrahedron: Asymmetry 1996 , 7 , 285 .
   Web of Science ®Google Scholar
• (a) 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 ; (b) Gazit , A. ; Osherov , N. ; Posner , I. ; Yaish , P. ; Poradosu , E. ; Gilon , C. ; Levitzki , A. Tyrphostins, II: Heterocyclic and α-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases . J. Med. Chem. 1991 , 34 , 1896 .
   Web of Science ®Google Scholar
• Pavan Kumar , V. ; Prakash Reddy , V. ; Sridhar , R. ; Srinivas , B. ; Narender , M. ; Rama Rao , K. Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water . J. Org. Chem. 2008 , 73 , 1646 .
   PubMed Web of Science ®Google Scholar
• Mayer , S. ; Merour , J.-Y. ; Joseph , B. Guillamet, G. Synthesis and reactivity of 1,4-oxazinoindole derivatives . Eur. J. Org. Chem. 2002 , 7–10 , 1646 .
   Google Scholar
• Bulbule , V. J. ; Jnaneshwara , G. K. ; Deshmukh , R. R. ; Borate , H. B. ; Deshpande , V. H. Benzyltrimethylammonium hydroxide–catalysed nitroaldol condensation . Synth. Commun. 2001 , 31 , 3623 .
   Web of Science ®Google Scholar
• Ishikawa , T. ; Mizuta , T. ; Hagiwara , K. ; Aikawa , T. ; Kudo , T. ; Saito , S. Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base . J. Org. Chem. 2003 , 68 , 3702 .
   PubMed Web of Science ®Google Scholar
• Chaturvedi , D. ; Ray , S. A high yielding, one-pot, Triton B–catalyzed synthesis of dithiocarbamates using alcoholic tosylates . Monatsh. Chem. 2006 , 137 , 465 .
   Web of Science ®Google Scholar
• (a) Varma , R. S. ; Meshram , H. M. Solid state deoximation with ammonium persulfate–silica gel: Regeneration of carbonyl compounds using microwaves . Tetrahedron Lett. 1997 , 38 , 5427 ; (b) Varma , R. S. ; Meshram , H. M. Solid state cleavage of semicarbazones and phenylhydrazones with ammonium persulfate–clay using microwave or ultrasonic irradiation . Tetrahedron Lett. 1997 , 38 , 7973 ; (c) Meshram , H. M. ; Reddy , G. S. ; Yadav , J. S. Clay-supported ammonium nitrate “Clayan”: A mild and eco-friendly reagent for dethioacetalization . Tetrahedron Lett. 1997 , 38 , 8891 ; (d) Meshram , H. M. ; Ganesh , Y. S. S. ; Yadav , J. S. Clay-supported ammonium nitrate “Clayan”: A new reagent for selective nitration of arenes . Synth. Commun. 2003 , 33 , 2497 .
   Web of Science ®Google Scholar