RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(18): 2593-2599
DOI: 10.1055/s-0033-1338506
DOI: 10.1055/s-0033-1338506
paper
Efficient One-Pot Synthesis of Spirooxindole Derivatives Bearing Hexahydroquinolines Using Multicomponent Reactions Catalyzed by Ethylenediamine Diacetate
Weitere Informationen
Publikationsverlauf
Received: 18. Mai 2013
Accepted after revision: 24. Juni 2013
Publikationsdatum:
19. Juli 2013 (online)
Abstract
A simple and efficient one-pot synthesis of biologically interesting spirooxindole derivatives bearing hexahydroquinoline skeleton was accomplished by EDDA-catalyzed, three-component reactions between isatins, malononitrile, and enaminones in good yields. The value of this methodology lies in its inexpensive and nontoxic organocatalyst, mild reaction conditions, and ease of handling.
Key words
multicomponent reaction - spirooxindoles - enaminone - hexahydroquinolines - ethylenediamine diacetateSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Robert A, Dechy-Cabaret O, Cazelles J, Meunier B. Acc. Chem. Res. 2002; 35: 167
- 1b Ridley RG. Nature 2002; 415: 686
- 1c Carosati E, Mannhold R, Wahl P, Hansen JB, Fremming T, Zamora I, Cianchetta G, Baroni M. J. Med. Chem. 2007; 50: 2117
- 1d Matsuyama N, Kato T, Kimura K, Mizutani T, Saeki K. J. Health Sci. 2006; 52: 821
- 1e Nayyar A, Malde A, Jain R, Coutinho E. Bioorg. Med. Chem. 2006; 14: 847
- 1f Kym PR, Kort ME, Coghlan MJ, Moore JL, Tang R, Ratajczyk JD, Larson DP, Elmore SW, Pratt JK, Stashko MA, Falls HD, Lin CW, Nakane M, Miller L, Tyree CM, Miner JN, Jacobson PB, Wilcox DM, Nguyen P, Lane BC. J. Med. Chem. 2003; 46: 1016
- 1g Heitsch H. Curr. Med. Chem. 2002; 9: 913
- 1h Narender P, Srinivas U, Ravinder M, Rao BA, Ramesh C, Harakishore K, Gangadasu B, Murthy US. N, Rao VJ. Bioorg. Med. Chem. 2006; 14: 4600
- 1i Muruganantham N, Sivakumar R, Anbalagan N, Gunasekaran V, Leonard JT. Biol. Pharm. Bull. 2004; 27: 1683
- 1j Tsotinis A, Vlachou M, Zouroudis S, Jeney A, Timar F, Thurston DE, Roussakis C. Lett. Drug Des. Discov. 2005; 2: 189
- 1k Joshi AA, Viswanathan CL. Bioorg. Med. Chem. Lett. 2006; 16: 2613
- 2a El-Sabbagh OI, Shabaan MA, Kadry HH, Al-Din ES. Arch. Pharm. (Weinheim, Ger.) 2010; 9: 519
- 2b Al-Said MS, Ghorab MM, Al-Dosari MS, Hamed MM. Eur. J. Med. Chem. 2011; 46: 201
- 2c Alqasoumi SI, Al-taweel AM, Alafeefy AM, Hamed MM, Noaman E, Ghorab MM. Bioorg. Med. Chem. Lett. 2009; 19: 6939
- 2d Gündüz MG, Öztürk GS, Vural İM, Şimşek R, Sarioğlu Y, Şafak C. Eur. J. Med. Chem. 2008; 43: 562
- 2e León R, de los Ríos C, Marco-Contelles J, Huertas O, Barril X, Luque FJ, López MG, García AG, Villarroya M. Bioorg. Med. Chem. 2008; 16: 7759
- 2f Miri R, Javidnia K, Mirkhani H, Hemmateenejad B, Sepeher Z, Zalpour M, Behzad T, Khoshneviszadeh M, Edraki N, Mehdipour AR. Chem. Biol. Drug Des. 2007; 70: 329
- 3a Godfraid T, Miller R, Wibo M. Pharmacol. Rev. 1986; 38: 321
- 3b Mager PP, Coburn RA, Solo AJ, Triggle DJ, Rothe H. Drug. Des. Discov. 1992; 8: 273
- 3c Mannhold R, Jablonka B, Voigt W, Schöenafinger K, Schraven E. Eur. J. Med. Chem. 1992; 27: 229
- 3d Triggle DJ, Langs DA, Janis RA. Med. Res. Rev. 1989; 9: 123
- 3e Shan R, Velazquez C, Knaus EE. J. Med. Chem. 2004; 47: 254
- 3f Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H. J. Med. Chem. 2004; 47: 2853
- 4a Aruoma O, Smith C, Cecchini R, Evans P, Halliwell B. Biochem. Pharmacol. 1991; 42: 735
- 4b Hilgeroth A. Mini-Rev. Med. Chem. 2002; 2: 235
- 4c Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnár J. Bioorg. Med. Chem. 2002; 10: 1051
- 5a Klusa V. Drugs Future 1995; 20: 135
- 5b Boer R, Gekeler V. Drugs Future 1995; 20: 499
- 5c Sausins A, Duburs G. Heterocycles 1988; 27: 279
- 5d Bretzel RG, Bollen CC, Maester E, Federlin KF. Am. J. Kidney Dis. 1993; 21: 54
- 6a Agarwal A, Chauhan PM. S. Tetrahedron Lett. 2005; 46: 1345
- 6b Öhberg L, Westman J. Synlett 2001; 1296
- 7a Sridhar R, Perumal PT. Tetrahedron 2005; 61: 2465
- 7b Ji SJ, Jiang ZQ, Lu J, Loh TP. Synthesis 2004; 831
- 8 Kassaee MZ, Masrouri H, Movahedi F. Monatsh. Chem. 2010; 141: 317
- 9 Tewari N, Dwivedi N, Tripathi RP. Tetrahedron Lett. 2004; 45: 9011
- 10 Karade NN, Budhewar VH, Shinde SV, Jadhav WN. Lett. Org. Chem. 2007; 4: 16
- 11 Das B, Ravikanth B, Ramu R, Rao BV. Chem. Pharm. Bull. 2006; 54: 1044
- 12 Maheswara M, Siddaiah V, Rao YK, Tzeng Y, Sridhar C. J. Mol. Catal. A: Chem. 2006; 260: 179
- 13 Debache A, Tafer R, Boulcina R, Belfaitah A, Rhouati S, Carboni B. Synthesis 2008; 2112
- 14 Sabitha G, Reddy GS. K. K, Reddy CS, Yadav JS. Tetrahedron Lett. 2003; 44: 4129
- 15 Ko S, Yao CF. Tetrahedron 2006; 62: 7293
- 16a Wang LM, Sheng Z, Zhang L, Han JW, Fan Z, Tian H, Qian CT. Tetrahedron 2005; 61: 1539
- 16b Donelson JL, Gibbs RA, De SK. J. Mol. Catal. A: Chem. 2006; 256: 309
- 17a Legeay JC, Goujon JY, Eynde JJ. V, Toupet L, Bazureau JP. J. Comb. Chem. 2006; 8: 829
- 17b Dondoni A, Massi A, Minghini E, Bertolasi V. Tetrahedron 2004; 60: 2311
- 18a Lee JH. Tetrahedron Lett. 2005; 46: 7329
- 18b Kumar A, Maurya RA. Tetrahedron Lett. 2007; 48: 3887
- 19 Cherkupally SR, Mekala R. Chem. Pharm. Bull. 2008; 56: 1002
- 20a Williams RM, Cox RJ. Acc. Chem. Res. 2003; 36: 127
- 20b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 20c Cui CB, Kakeya H, Osada H. J. Antibiot. 1996; 49: 832
- 20d Cui CB, Kakeya H, Osada H. Tetrahedron 1996; 52: 12651
- 20e Cui CB, Kakeya H, Osada H. Tetrahedron 1997; 53: 59
- 20f Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H. J. Antibiot. 1995; 48: 1382
- 20g Cui CB, Kakeya H, Okada G, Onose R, Osada H. J. Antibiot. 1996; 49: 527
- 20h Cui CB, Kakeya H, Osada H. J. Antibiot. 1996; 49: 534
- 20i Kang TH, Matsumoto K, Tohda M, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H. Eur. J. Pharmacol. 2002; 444: 39
- 20j Rahman A, Silva WS. J, Alvi KA, De Silva KT. D. Phytochemistry 1987; 26: 865
- 20k Rahman A, Qureshi MM, Muzaffar A, De Silva KT. D. Heterocycles 1988; 27: 725
- 20l Harada M, Ozaki Y. Chem. Pharm. Bull. 1978; 26: 48
- 21a Fischer C, Meyers C, Carreira EM. Helv. Chim. Acta 2000; 83: 1175
- 21b Alper PB, Meyers C, Lerchner A, Siegel DR, Carreira EM. Angew. Chem. Int. Ed. 1999; 38: 3186
- 21c Ashimori A, Bachand B, Overman LE, Poon DJ. J. Am. Chem. Soc. 1998; 120: 6477
- 21d Matsuura T, Overman LE, Poon DJ. J. Am. Chem. Soc. 1998; 120: 6500
- 21e Cui CB, Kakeya H, Osada H. Tetrahedron 1996; 52: 12651
- 22a Fuchs JR, Funk RL. Org. Lett. 2005; 7: 677
- 22b Yong SR, Ung AT, Pyne SG, Skelton BW, White AH. Tetrahedron 2007; 63: 1191
- 22c Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY.-H, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2105
- 22d Yong SR, Williams MC, Pyne SG, Ung AT, Skelton BW, White AH, Turner P. Tetrahedron 2005; 61: 8120
- 22e Feldman KS, Vidulova DB, Karatjas AG. J. Org. Chem. 2005; 70: 6429
- 22f Osman FH, Samahy FA. Tetrahedron 2000; 56: 1863
- 22g Mao Z, Baldwin SW. Org. Lett. 2004; 6: 2425
- 22h Feldman KS, Karatjas AG. Org. Lett. 2006; 8: 4137
- 22i Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
- 22j Robertson DW, Krushinski JH, Pollock GD, Wilson H, Kauffman RF, Hayes JS. J. Med. Chem. 1987; 30: 824
- 22k Sebahar PR, Osada H, Usui T, Williams RM. Tetrahedron 2002; 58: 6311
- 22l Lo MM.-C, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL. J. Am. Chem. Soc. 2004; 126: 16077
- 23a Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 23b Dömling A. Chem. Rev. 2006; 106: 17
- 23c Zhu J. Eur. J. Org. Chem. 2003; 1133
- 24 Gao S, Tsai CH, Tseng C, Yao CF. Tetrahedron 2008; 64: 9143
- 25 Zhu S.-L, Ji SJ, Zhang Y. Tetrahedron 2007; 63: 9365
- 26 Shanthi G, Subbulakshmi G, Perumal PT. Tetrahedron 2007; 63: 2057
- 27 Elinson MN, Ilovaisky AI, Dorofeev AS, Merkulova VM, Stepanov NO, Miloserdov FM, Ogibin YN, Nikishin GI. Tetrahedron 2007; 63: 10543
- 28 Zhu S.-L, Zhao K, Su X.-M, Ji S.-J. Synth. Commun. 2009; 39: 1355
- 29a Bolm C, Rantanen T, Schiffers I, Zani L. Angew. Chem. Int. Ed. 2005; 44: 1758
- 29b Berrisford DJ, Bolm C, Sharpless KB. Angew. Chem. Int. Ed. 1995; 34: 1059
- 29c Saito S, Nakadai M, Yamamoto H. Synlett 2001; 1245
- 29d Saito S, Yamamoto H. Acc. Chem. Res. 2004; 37: 570
- 30a Lee YR, Choi JH, Yoon SH. Tetrahedron Lett. 2005; 46: 7539
- 30b Lee YR, Lee WK, Noh SK, Lyoo WS. Synthesis 2006; 853
- 30c Lee YR, Kim DH. Synthesis 2006; 603
- 30d Lee YR, Kim JH. Synlett 2007; 2232
- 30e Wang X, Lee YR. Tetrahedron Lett. 2007; 48: 6275
- 30f Wang X, Lee YR. Synthesis 2007; 3044
- 30g Lee YR, Xia L. Synthesis 2007; 3240
- 30h Lee YR, Kim YM. Helv. Chim. Acta 2007; 90: 2401
- 30i Lee YR, Li X, Kim JH. J. Org. Chem. 2008; 73: 4313
- 30j Xia L, Lee YR. Synlett 2008; 1643
- 30k Lee YR, Hung TV. Tetrahedron 2008; 64: 7338
- 30l Lee YR, Xia L. Tetrahedron Lett. 2008; 49: 3283
- 30m Wang X, Lee YR. Tetrahedron 2009; 65: 10125
- 30n Lee YR, Kim YM, Kim SH. Tetrahedron 2009; 65: 101
- 30o Jung DH, Lee YR, Kim SH. Helv. Chim. Acta 2010; 93: 635
- 30p Kolla SR, Lee YR. Tetrahedron 2010; 66: 8938
- 30q Park BH, Lee HJ, Lee YR. J. Nat. Prod. 2011; 74: 644
- 30r Wang X, Lee YR. Tetrahedron 2011; 67: 9179
- 30s Narasimhulu M, Lee YR. Tetrahedron 2011; 67: 9627
- 30t Kolla SR, Lee YR. Tetrahedron 2012; 68: 226
- 30u Pandit RP, Lee YR. Synthesis 2012; 44: 2910
- 31 Hari GS, Lee YR. Synthesis 2010; 453