Tungstic acid-catalyzed synthesis of 3,3-bis (1H-indol-3-yl)indolin-2-one derivatives

Heterocyclic Communications

Volumn 19, Issue 6, 2013, Pages 421-424

  Patel, Gautam M ^a   Deota, Pradeep T ^a  

^a M S UNIVERSITY OF BARODA   (India)

Author keywords

indole; isatin; oxindole; tungstic acid

Indexed keywords

EID: 84889666628     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/hc-2013-0142     Document Type: Article

References (37)

1. Gilchrist, T. L. Heterocyclic chemistry. Academic Press: London, 1997, pp. 231.
2. Demirayak, S.; Kayagil, I.; Yurttas, L. Microwave supported synthesis of some novel 1,3-diarylpyrazino [1,2-a] benzimidazole derivatives and investigation of their anticancer activities Eur. J. Med. Chem. 2011, 46, 411-416.
3. Ito, H.; Sakakibara, J.; Ueda T. Antitumor effect of 6-phenyl- 7(6H)-isoselenazolo [4,3-d]pyrimidone on the growth of Ehrlich ascites tumor. Cancer Lett. 1985, 28, 61-68. (Pubitemid 16245405)
4. Natarajan, A.; Fan, Y. H.; Chen, H.; Guo, Y.; Iyasere, J.; Harbinski, F.; Christ, W. J.; Aktas, H.; Halperin, J. A. 3,3-Diaryl- 1,3-dihydroindol-2-ones as antiproliferatives mediated by translation initiation inhibition. J. Med. Chem. 2004, 47, 1882-1885. (Pubitemid 38453906)
5. Ratan Bal, T.; Anand, B.; Yogeeswari, P.; Sriram, D. Synthesis and evaluation of anti-HIV activity of isatin -thiosemicarbazone derivatives Bioorg. Med. Chem. Lett. 2005, 15, 4451-4455. (Pubitemid 41253873)
6. Tripathy, R.; Reiboldt, A.; Messina, P. A.; Iqbal, M.; Singh, J.; Bacon, E. R.; Angeles, Th. S.; Yang, Sh. X.; Albom, M. S.; Robinson, C.; et al. Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis Bioorg. Med. Chem. Lett. 2006, 16, 2158-2162. (Pubitemid 43351070)
7. Amal Raj, A.; Raghunathan, R.; Sridevikumaria, M. R.; Raman, N. Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg. Med. Chem. 2003, 11, 407-419. (Pubitemid 36051031)
8. Maskell, L.; Blanche, E. A.; Colucci, M. A.; Whatmore, J. L.; Moody, Ch. J. Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles. Bioorg. Med. Chem. Lett. 2007, 17, 1575-1578. (Pubitemid 46274355)
9. Zhang, H. P.; Kamano, Y.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Isolation and structure of convolutamydines B-D from marine bryozoan Amathia convoluta. Tetrahedron 1995, 51, 5523-5528.
10. Khuzhaev, V. U.; Zhalolov, I.; Turguniv, K. K.; Tashkhodzhaev, B.; Levkovich, M. G.; Arpova, S. F.; Shashkov, A. S. Alkaloids from Arundo donax: XVII. Structure of the dimeric indole alkaloid arundaphine. Chem. Nat. Compd. 2004, 40, 269-272. (Pubitemid 39187890)
11. Rasmussen, H. B.; MacLeod, J. K. Total synthesis of donaxaridine. J. Nat. Prod. 1997, 60, 1152-1154. (Pubitemid 27516209)
12. Kagata, T.; Saito, S.; Shigemori, H.; Ohsaki, A.; Ishiyama, H.; Kubota, T.; Kobayashi, J. Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare. J. Nat. Prod. 2006, 69, 1517-1521. (Pubitemid 44899773)
13. Tang, Y. Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X. Z. Maremycins C and D, new diketopiperazines, and maremycins E and F, novel polycyclic spiro-indole metabolites isolated from Streptomyces sp. Eur. J. Org. Chem. 2001, 66, 261-267. (Pubitemid 32104359)
14. Jursic, B. S.; Stevens, E. D. Preparation of dibarbiturates of oxindole by condensation of isatin and barbituric acid derivatives. Tetrahedron Lett. 2002, 43, 5681-5683. (Pubitemid 34786540)
15. 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. (Pubitemid 28334266)
16. Marsden, S. P.; Watson, E. L.; Raw, S. A. Facile and general synthesis of quaternary 3-aminooxindoles. Org. Lett. 2008, 10, 2905-2908
17. Felpin, F. X.; Ibarguren, O.; Nassar Hardy, L.; Fouquet, E. Synthesis of oxindoles by tandem Heck-reduction-cyclization (HRC) from a single bifunctional, in situ generated Pd/C catalyst. J. Org. Chem. 2009, 74, 1349-1352
18. Malkov, A. V.; Kabeshov, M. A.; Bella, M.; Kysilka, O.; Malyshev, D. A.; Pluhackova, K.; Kocovsky, P. Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: application in the synthesis of convolutamydine A. Org. Lett. 2007, 9, 5473-5476.
19. Azizian, J.; Mohammadi, A.; Karimi, N.; Mohammadizadeh, M.; Karimi, A. Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives. Catal. Commun. 2006, 7, 752-755. (Pubitemid 44374418)
20. Chatterjee, A.; Manna, S.; Benerji, J.; Prange, T.; Shoolery, J. Lewis-acid-induced electrophilic substitution in indoles with acetone Part 2. J. Chem. Soc. Perkin Trans. I 1980, 553-555.
21. Babu, G.; Sridhar, N.; Perumal, P. T. A convenient method of synthesis of bis-indolylmethanes: indium trichloride catalyzed reactions of indole with aldehydes and Schiffs bases. Synth. Commun. 2000, 30, 1609-1614. (Pubitemid 30205356)
22. Nagarajan, R.; Perumal, P. InCl3 and In(OTf)3 catalyzed reactions: synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron 2002, 58, 1229-1232. (Pubitemid 34112600)
23. Chen, D. P.; Yu, L. B.; Wang, P.G. Lewis acid-catalyzed reactions in protic media: lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 1996, 37, 4467-4470. (Pubitemid 26257349)
24. Mi, X.; Lu, S.; He, 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. (Pubitemid 38610388)
25. Gibbs, T. J. K.; Tomkinson, N. C. O. Aminocatalytic preparation of bisindolylalkanes. Org. Biomol. Chem. 2005, 3, 4043-4045. (Pubitemid 41729658)
26. Yadav, J. S.; Reddy, B. V. S.; Sunitha, S. Efficient and eco-friendly process for the synthesis of bis(1H-indol-3-yl) methanes using ionic liquids. Adv. Synth. Catal. 2003, 345, 349-352. (Pubitemid 37393195)
27. 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 Chem. 2006, 244, 168-172. (Pubitemid 43121411)
28. Ko, S.; Lim, C.; Tu, Z.; Wang, Y. F.; Wang, C. C.; Yao, C. F. CAN and iodine-catalyzed reaction of indole or 1-methylindole with -unsaturated ketone or aldehyde. Tetrahedron Lett. 2006, 47, 487-492. (Pubitemid 41797380)
29. Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S.; Kumar, G. M.; Madan, C. Lithium perchlorate catalyzed reactions of indoles: an expeditious synthesis of bis(indolyl)methanes. Synthesis 2001, 5, 783-788.
30. Bandgar, B. P.; Shaikh, K. A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959-1961. (Pubitemid 36183442)
31. Singh, V. K.; Deota, P. T. Tungstic acid-hydrogen peroxide a simple reagent for oxidation of cycloocta-1,5-diene preparation of (Z) cyclooct-5-ene-trans-1,2-diol and 1,6-dicarbomethoxy (Z) hex-3-ene. Synth. Commun. 1988, 18, 617-624.
32. Deota, P. T.; Desai, R.; Valodkar, V. B., Reaction of tungstic acid-hydrogen peroxide with endo-dicyclopentadiene: an unusual observation. J. Chem. Res. (S) 1998, 9, 562-563. (Pubitemid 128527006)
33. Hui, C.; Wei-Lin, D.; Ruihua, G.; Yong, C.; Hexing, L.; Kangnian, F. New green catalytic manufacture of glutaric acid from the oxidation of cyclopentane-1,2-diol with aqueous hydrogen peroxide. Appl. Catal. A Gen. 2007, 328, 226-236.
34. Moghadam, K. R.; Kiasaraie, M. S.; Amlashi, H. T. Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids. Tetrahedron 2010, 66, 2316-2321.
35. Tabatabaeian, K.; Mamaghani, M; Mahmoodi, N; Khorshidi, A. Ruthenium-catalyzed efficient routes to oxindole derivatives. Can. J. Chem. 2009, 87, 1213-1217.
36. Kamal, A.; Srikanth, Y. V. V.; Khan, N. A.; Shaik, T. B.; Ashraf, M. Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity. Bioorg. Med. Chem. Lett. 2010, 20, 5229-5231, and references cited therein.
37. 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.