An efficient and clean synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones using ksf

Synthetic Communications

Volumn 40, Issue 23, 2010, Pages 3552-3560

  Nikpassand, Mohammad ^a   Mamaghani, Manouchehr ^a   Tabatabaeian, Khalil ^a   Samimi, Heshmat Alah ^b  

^a UNIVERSITY OF GUILAN   (Iran)

^b SHAHREKORD UNIVERSITY   (Iran)

Author keywords

3,3 Di(indolyl)indolin 2 ones; heterogeneous; indole; isatin; KSF

Indexed keywords

3 (1H INDOL 3 YL) 3 (1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (5 BROMO 1H INDOL 3 YL) 3 (1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(2 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(5 BROMO 1H INDOL 3 YL) 5 CHLOROINDOLIN 2 ONE; 3,3 BIS(5 BROMO 1H INDOL 3 YL)INDOLIN 2 ONE; 5 BROMO 3 (5 BROMO 1H INDOL 3 YL) 3 (1H INDOL 3 YL)INDOLIN 2 ONE; 5 BROMO 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 5 BROMO 3,3 BIS(2 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 5 BROMO 3,3 BIS(5 BROMO 1H INDOL 3 YL)INDOLIN 2 ONE; 5 CHLORO 3,3 BIS(2 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 5 CHLORO 3,3 DI(1H INDOL 3 YL)INDOLIN 2 ONE; INDOLE DERIVATIVE; ISATIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

EID: 78149420755     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903457399     Document Type: Article

References (31)

1. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1996.
2. 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.
3. 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.
4. Ramirez, A.; Garcia-Rubio, S. Current progress in the chemistry and pharmacology of akuammiline alkaloids. Curr. Med. Chem. 2003, 10, 1891-1915.
5. 3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes=ketones or imines. Tetrahedron Lett. 2004, 45, 4567-4570.
6. 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.
7. 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.
8. 2O/LiI. Tetrahedron Lett. 2007, 48, 8040-8042.
9. Humphrey, G. R.; Kuethe, J. T. Practical methodologies for the synthesis of indoles. Chem. Rev. 2006, 106, 2875-2911.
10. 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.
11. 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.
12. 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.
13. Szmuszkovicz, J. The reaction of substituted indoles with methyl vinyl ketone. New synthesis of 2-methylcarbazole. J. Am. Chem. Soc. 1957, 79, 2819-2821.
14. Roomi, M.; Macdonald, S. F. Reductive C-alkylation. II. Can. J. Chem. 1970, 48, 139-143.
15. 3-catalyzed 1,4- then 1,2-nucleophilic addition to enones. J. Org. Chem. 2002, 67, 3700-3704.
16. 2O. Synlett. 1996, 1047-1050.
17. 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. I1980, 553-555.
18. 12O40), 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.
19. 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.
20. Bergman, J.; Eklund, N. Synthesis and studies of tris-indolobenzenes and related compounds. Tetrahadron 1980, 36, 1445-1450.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. Balogh, M.; Laszlo, P. Organic Chemistry Using Clay; Springer Verlag: New York, 1993.
27. 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.
28. 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.
29. 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.
30. III-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones. J. Mol. Catal. A 2007, 270, 112-116.
31. III-catalyzed condensation of indoles and aldehydes or ketones. Can. J. Chem. 2006, 84, 1541-1545.