Abstract
A simple, efficient, solvent-free, and mild method for the preparation of di(indolyl)indoline-2-ones (symmetrical and unsymmetrical), have been reported in the presence of HNO3@nano SiO2 under both stirring and grinding techniques at room temperature successfully.
References
Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y (2006) Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2. Bioorg Med Chem Lett 109:2109–2112
Chen LR, Wang YCh, Lin YW, Chou Sh, Chen Sh, Liu LT, Wu YT, Kuo Ch, Chen Juang Sh (2005) Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg Med Chem Lett 15:3058–3062
Denoyelle S, Chen T, Yang H, Chen L, Zhang Y, Halperin JA, Aktas BH, Chorev M (2013) Synthesis and SAR study of novel 3,3-diphenyl-1,3-dihydroindol-2-one derivatives as potent eIF2·GTP·Met-tRNAiMet ternary complex inhibitors. Eur J Med Chem 69:537–553
Tripathy R, Reiboldt A, Messina PA, Iqbal M, Singh J, Bacon ER, Angeles Th, Yang Sh, Albom MS, Robinson C, Chang H, Ruggeri BA, Mallamo JP (2006) Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis. Bioorg Med Chem Lett 16:2158–2161
Azizian J, Mohammadi AA, Karimi N, Mohammadizadeh MR, Karimi AR (2006) Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives. Catal Commun 7:752–755
Kumar A, Shukla RD, Yadav D, Gupta LP (2015) Friedel–Crafts alkylation of indoles in deep eutectic solvent. RSC Adv 5:52062–52065
Saffar-Teluri A (2014) Boron trifluoride supported on nano-SiO2: an efficient and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes and oxindole derivatives. Res Chem Intermed 40:1061–1067
Subba Reddy BV, Rajeswari N, Sarangapani M, Prashanthi Y, Ganji RJ, Addlagatta A (2012) Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl) indolin-2-ones and evaluation of their cytotoxicity. Bioorg Med Chem Lett 22:2460–2463
Alimohammadi K, Sarrafi Y, Tajbakhsh M (2008) H6P2W18O62: a green and reusable catalyst for the synthesis of 3,3-diaryloxindole derivatives in water. Monatsh Chem 139:1037–1039
Wang Sh, Ji Sh (2006) Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation. Tetrahedron 62:1527–1530
Nikpasand M, Mamaghani M, Tabatabaeian Kh, Samimi HA (2010) An efficient and clean synthesis of symmetrical and unsymmetrical 3,3-di(indolyl) indolin-2-ones using KSF. Synth Commun 40:3552–3560
Rad-Moghadam K, Sharifi-Kiasaraie M, Taheri-Amlashi H (2010) Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl) indolin-2-ones under controlled catalysis of ionic liquids. Tetrahedron 66:2316–2319
Khodaei MM, Mohammadpoor-Baltork I, Memarian HR, Khosropour AR, Nikoofar K, Ghanbary P (2008) Synthesis of 3-substituted indoles promoted by pulverization-activation method catalyzed by Bi(NO3)3·5H2O. J Heterocycl Chem 45:377–381
Ghanbari K, Nikoofar K (2014) Electrosynthesis of 3,3-di (indolyl) indolin-2-one nanorods. Monatsh Chem 145:1867–1871
Haghighi M, Nikoofar K (2016) Nano TiO2/SiO2: an efficient and reusable catalyst for the synthesis of oxindole derivatives. J Saudi Chem Soc 20:101–106
Nikoofar K, Khalili Z (2016) Nano-SiO2: a heterogeneous and reusable catalyst for the one-pot synthesis of symmetrical and unsymmetrical 3,3-di(aryl)indolin-2-ones under solvent-free conditions. Z Naturforsch 1:31–36
Azizian J, Fallah-Bagher-Shaidaei H, Kefayati H (2003) A facile one-pot method for the preparation of N-alkyl isatins under microwave irradiation. Synth Commun 33:789–793
Nikoofar K, Moazzez Dizgarani Sh (2015) HNO3@ nano SiO2: an efficient catalytic system for the synthesis of multi-substituted imidazoles under solvent-free conditions. J Suadi Chem Soc. https://doi.org/10.1016/j.jscs.2015.11.006
Bergman J, Eklund N (1980) Synthesis and studies of tris-indolobenzenes and related compounds. Tetrahedron 36:1445–1450
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Nikoofar, K., Khalili, Z. HNO3@nano SiO2 Catalyzed Green and Efficient Synthesis of Symmetrical and Unsymmetrical Di(indolyl)indoline-2-ones by Stirring and Grindstone Methods. Natl. Acad. Sci. Lett. 41, 361–364 (2018). https://doi.org/10.1007/s40009-018-0710-6
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DOI: https://doi.org/10.1007/s40009-018-0710-6