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Synthesis 2012; 44(11): 1725-1735
DOI: 10.1055/s-0031-1290773
DOI: 10.1055/s-0031-1290773
paper
Highly Efficient Synthesis of Novel Morita–Baylis–Hillman Adducts from Activated Ketones Using a DABCO-Based Hydroxy Ionic Liquid (HIL) as a Recyclable Catalyst-Solvent
Further Information
Publication History
Received: 12 January 2012
Accepted after revision: 27 February 2012
Publication Date:
04 May 2012 (online)
Abstract
A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita–Baylis–Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita–Baylis–Hillman reaction due to its operational simplicity, high yields, dual catalyst-solvent properties, and excellent recyclability and reusability. This hydroxy ionic liquid acts as a protic solvent and tertiary amine for the preparation of biologically active compounds from isatin, ninhydrin, 1,2-acenaphthylenequinone, and benzil with high yields and very short reaction times.
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References and Notes
- 1 Kamimura A, Morita R, Matsuura K, Omata Y, Shirai M. Tetrahedron Lett. 2002; 43: 6189
- 2 Morita K. JP 6,803,364, 1968 ; Chem. Abstr. 1968, 69, 58828s
- 3 Toyo Rayon Co., Ltd. FP 1,506,132, 1967 ; Chem. Abstr. 1969, 70, 19613u
- 4 Baylis AB, Hillman ME. D. DE 2,155,133, 1972 ; Chem. Abstr. 1972, 77, 34174q
- 5a Morita K, Suzuki Z, Hirose H. Bull. Chem. Soc. Jpn. 1968; 41: 2815
- 5b Basavaiah D, Rao AJ, Satyanarayana T. Chem. Rev. 2003; 103: 811
- 5c Basavaiah D, Rao KV, Reddy RJ. Chem. Soc. Rev. 2007; 36: 1581
- 6 Basavaiah D, Hyma RS, Kumaragurubaran N. Tetrahedron 2000; 56: 5905
- 7 Kaye PT, Musa MA. Synth. Commun. 2003; 33: 1755
- 8 Patra A, Batra S, Bhaduri AP, Khanna A, Chander R, Dikshit M. Bioorg. Med. Chem. 2003; 11: 2269
- 9 de Souza RO. M. A, Meireles BA, Aguiar CS, Vasconcellos M. Synthesis 2004; 1595
- 10 Kundu MK, Sundar N, Kumar SK, Bhat SV, Biswas S, Valecha N. Bioorg. Med. Chem. Lett. 1999; 9: 731
- 11 de Souza RO. M. A, Pereira VL. P, Muzitano MF, Falcao CA. B, Rossi-Bergmann B, Filho EB. A, Vasconcellos M. Eur. J. Med. Chem. 2007; 42: 99
- 12 Vasconcellos M, Silva TM. S, Camara CA, Martins RM, Lacerda KM, Lopes HM, Pereira VL. P, de Souza RO. M. A, Crespo LT. C. Pest Manage. Sci. 2006; 62: 288
- 13a Ameer F, Drewes SE, Freese SD, Kaye PT. Synth. Commun. 1988; 18: 495
- 13b Drewes SE, Freese SD, Emslie ND, Roos GH. P. Synth. Commun. 1988; 18: 1565
- 13c Marko IE, Ollis WD, Rasmussen PR. Tetrahedron Lett. 1990; 31: 4509
- 13d Marko IE, Giles PR, Hindley NJ. Tetrahedron 1997; 53: 1015
- 13e Rezgui F, El Gaied MM. Tetrahedron Lett. 1998; 39: 5965
- 13f Aggarwal VK, Mereu A. Chem. Commun. 1999; 2311
- 13g Leadbeater NE, van der Pol C. J. Chem. Soc., Perkin Trans. 1 2001; 2831
- 13h Octavio R, de Souza MA, Vasconcellos ML. A. A. Synth. Commun. 2003; 33: 1383
- 13i Aggarwal VK, Emme I, Fulford SY. J. Org. Chem. 2003; 68: 692
- 13j Luo S, Wang PG, Cheng J.-P. J. Org. Chem. 2004; 69: 555
- 13k Luo S, Mi X, Xu H, Wang PG, Cheng J.-P. J. Org. Chem. 2004; 69: 8413
- 13l Mi X, Luo S, Cheng J.-P. J. Org. Chem. 2005; 70: 2338
- 14a Roth F, Gygax P, Frater G. Tetrahedron Lett. 1992; 33: 1045
- 14b Li W, Zhang Z, Xiao D, Zhang X. J. Org. Chem. 2000; 65: 3489
- 14c Wang L.-C, Luis AL, Agapiou K, Jang H.-Y, Krische MJ. J. Am. Chem. Soc. 2002; 124: 2402
- 14d Frank SA, Mergott DJ, Roush WR. J. Am. Chem. Soc. 2002; 124: 2404
- 15a Aggarwal VK, Tarver GJ, McCague R. Chem. Commun. 1996; 2713
- 15b Aggarwal VK, Mereu A, Tarver GJ, McCague R. J. Org. Chem. 1998; 63: 7183
- 15c Li G, Wei H, Gao JJ, Caputo TD. Tetrahedron Lett. 2000; 41: 1
- 15d Shi M, Jiang J, Cui S. Molecules 2001; 6: 852
- 15e Basavaiah D, Sreenivasulu B, Reddy RM, Muthukumaran K. Synth. Commun. 2001; 31: 2987
- 15f Basavaiah D, Sreenivasulu B, Rao AJ. J. Org. Chem. 2003; 68: 5983
- 16 Kundu MK, Mukherjee SB, Balu N, Padmakumar R, Bhat SV. Synlett 1994; 444
- 17 Coelho F, Almeida WP, Veronese D, Mateus CR, Lopes EC. S, Rossi RC, Silveira GP. C, Pavam CH. Tetrahedron 2002; 58: 7437
- 18 Shi M, Jiang JK, Cui SC. Tetrahedron 2001; 57: 7343
- 19 Pellissier H. Tetrahedron 2007; 63: 9267
- 20 Wilkes JS, Zaworotko MJ. J. Chem. Soc., Chem. Commun. 1992; 965
- 21a Wassercheid P, Keim W. Angew. Chem. Int. Ed. 2000; 39: 3772
- 21b Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667
- 21c Zhao D, Wu M, Kou Y, Min E. Catal. Today 2002; 74: 157
- 21d Kitazume T, Tamura K, Jiang Z, Miyake N, Kawasaki I. J. Fluorine Chem. 2002; 115: 49
- 21e Poole CF. J. Chromatogr., A 2004; 49: 1037
- 21f Kawasaki I, Tsunoda K, Tsuji T, Yamaguchi T, Shibuta H, Uchida N, Yamashita M, Ohta S. Chem. Commun. 2005; 2134
- 22 Earle MJ, Katdare SP, Seddon KR. Org. Lett. 2004; 6: 707
- 23a Earle MJ, McCormac PB, Seddon KR. Green Chem. 1999; 1: 23
- 23b Vijayaraghavan R, MacFarlane DR. Aust. J. Chem. 2004; 57: 129
- 23c Rosa JN, Afonso CA. M, Santos AG. Tetrahedron 2001; 57: 4189
- 24 Chauvin Y, Mussmann L, Olivier H. Angew. Chem., Int. Ed. Engl. 1995; 34: 2698
- 25a Klingshirn MA, Rogers RD, Shaughnessy KH. J. Organomet. Chem. 2005; 690: 3620
- 25b Mizushima E, Hayashi T, Tanaka M. Green Chem. 2001; 3: 76
- 26a Yadav JS, Reddy BV. S, Baishya G, Reddy KV, Narsaiah AV. Tetrahedron 2005; 61: 9541
- 26b Johansson M, Linden AA, Baeckvall J.-E. J. Organomet. Chem. 2005; 690: 3614
- 26c Serbanovic A, Branco LC, Nunes da Ponte M, Afonso CA. M. J. Organomet. Chem. 2005; 690: 3600
- 27a Picquet M, Stutzmann S, Tkatchenko I, Tommasi I, Zimmermann J, Wasserscheid P. Green Chem. 2003; 5: 153
- 27b Forsyth SA, Gunaratne HQ. N, Hardacre C, McKeown A, Rooney DW, Seddon KR. J. Mol. Catal. A: Chem. 2005; 231: 61
- 27c Reetz MT, Wiesenhöfer W, Francio G, Leitner W. Chem. Commun. 2002; 992
- 28a Sowmiah S, Srinivadesikan V, Tseng MC, Chu YH. Molecules 2009; 14: 3780
- 28b Chowdhury S, Mhan RS, Scott JL. Tetrahedron 2007; 63: 2363
- 29a Ubaidullaev KA, Shakirov R, Yunosov SY. Khim. Prir. Soedin. 1976; 12: 553
- 29b Rasmussen HB, MacLeod JK. J. Nat. Prod. 1997; 60: 1152
- 30a Kamano Y, Zhang H.-P, Ichihara Y, Kizu H, Komiyama K, Pettit GR. Tetrahedron Lett. 1995; 36: 2783
- 30b Zhang H.-P, Kamano Y, Ichihara Y, Kizu H, Komiyama K, Itokawa H, Pettit GR. Tetrahedron 1995; 51: 5523
- 30c Kamano Y, Kotake A, Hashima H, Hayakawa I, Hiraide H, Zhang H.-P, Kizu H, Komiyama K, Hayashi M, Pettit GR. Collect. Czech. Chem. Commun. 1999; 64: 1147
- 30d Garden SJ, Torres JC, Ferreira AA, Silva RB, Pinto AC. Tetrahedron Lett. 1997; 38: 1501
- 30e Miah S, Moody CJ, Richards IC, Slawin AM. Z. J. Chem. Soc., Perkin Trans. 1 1997; 2405
- 30f Jnaneshwara GK, Bedekar AV, Deshpande VH. Synth. Commun. 1999; 29: 3627
- 30g Jnaneshwar GK, Deshpande VH. J. Chem. Res., Synop. 1999; 632
- 31a Monde K, Sasaki K, Shirata A, Takasugi M. Phytochemistry 1991; 30: 2915
- 31b Suchy M, Kutschy P, Monde K, Goto H, Harada N, Takasugi M, Dzurilla M, Balentova E. J. Org. Chem. 2001; 66: 3940
- 32 Chung YM, Im YJ, Kim JN. Bull. Korean Chem. Soc. 2002; 23: 1651
- 33 Gardena SJ, Skakle JM. S. Tetrahedron Lett. 2002; 43: 1969
- 34 Basavaiah D, Bharathi TK, Gowriswari VV. L. Tetrahedron Lett. 1987; 28: 4351
- 35a Byun HS, Reddy KC, Bittman R. Tetrahedron Lett. 1994; 35: 1371
- 35b Auge J, Lubin N, Lubineau A. Tetrahedron Lett. 1994; 35: 7947
- 35c Rezgui F, El Gaied MM. Tetrahedron Lett. 1998; 39: 5965
- 35d Yu C, Liu B, Hu L. J. Org. Chem. 2001; 66: 5413
- 35e Cai J, Zhou Z, Zhao G, Tang C. Org. Lett. 2002; 4: 4723
- 35f Aggarwal VK, Dean DK, Mereu A, Williams R. J. Org. Chem. 2002; 67: 510
- 36a Luo SZ, Peng YY, Zhang BL, Wang PG, Cheng J.-P. Curr. Org. Synth. 2004; 1: 405
- 36b Luo SZ, Zhang BL, He JQ, Janczuk A, Wang PG, Cheng J.-P. Tetrahedron Lett. 2002; 43: 7369
- 36c Luo SZ, Mi XL, Wang PG, Cheng J.-P. Tetrahedron Lett. 2004; 45: 5171
- 37 Thomas M, Rothman L, Hathcher J, Agarkar P, Ramkirath R, Lall-Ramnarin S, Engel R. Synthesis 2009; 1437
- 38 Aggarwal VK, Mereu A. Chem. Commun. 1999; 2311
- 39 Selig PS, Miller SJ. Tetrahedron Lett. 2011; 52: 2148
- 40 Bode ML, Kaye PT. Tetrahedron Lett. 1991; 32: 5611
- 41 Foucaud A, Rouille E. Synthesis 1990; 787