European Journal of Chemistry

β-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water



Main Article Content

Swapna Kokkirala
Narayana Murthy Sabbavarapu
Venkata Durga Nageswar Yadavalli

Abstract

An experimentally simple, efficient Michael addition reaction was developed for the synthesis of various 1,8-dioxooctahydroxanthene derivatives with 1,3-cyclohexanedione/5,5-dimethyl 1,3-cyclohexane dione and different aldehydes by using β-cyclodextrin as a catalyst in water. A biomimetic approach was employed and the corresponding products were obtained in good to excellent yields. β-cyclodextrin can be recovered and reused upto four cycles without loss of catalytic activity.2_2_272_275_800

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Kokkirala, S.; Sabbavarapu, N. M.; Yadavalli, V. D. N. β-Cyclodextrin Mediated Synthesis of 1,8-Dioxooctahydroxanthenes in Water. Eur. J. Chem. 2011, 2, 272-275.

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References

[1]. Hideo, T. (1981) Jpn Tokkyo Koho JP 56005480.

[2]. Poupelin, J. P.; Saint-Ruf, G.; Foussard-Blanpin, O.; Narcisse, G.; Uchida Ernouf, G.; Lacroix, R. Eur. J. Med. Chem. 1978, 13, 67-75.

[3]. Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J. 1997, PCT Int. Appl. WO9706178.

[4]. Ion, R. M.; Planner, A.; Wiktorowicz, K.; Frackowiak. D. Acta Biochim. Pol. 1998, 45, 833-845.

[5]. Hatakeyma, S.; Ochi, N.; Numata, H.; Takano, S. J. Chem. Soc. Chem. Commun. 1988, 1202-1204.

[6]. Hilderbrand, S. A.; Weissleder, R. Tetrahedron Lett. 2007, 48, 4383-4385.
doi:10.1016/j.tetlet.2007.04.088
PMid:19834587 PMCid:2761723

[7]. Menchen, S. M.; Benson, S. C.; Lam, J. Y. L.; Zhen, W.; Sun, D.; Rosenblum, B. B.; Kha, S. H.; Taing, M. US Patent, 2003, 6,583, 168.

[8]. Banerjee, A.; Mukherjee, A. K. Stain Technol. 1981, 56, 83-85.
PMid:6166100

[9]. Reynolds, G. A.; Tuccio, S. A.; Peterson, O. G.; Specht, D. P. German Patent, 1971, DE2109040.

[10]. Horning, E. C.; Horning, M. G. J. Org. Chem. 1946, 11, 95-99.
doi:10.1021/jo01171a014
PMid:21013441

[11]. Wang, J. Q.; Harvey, R. G. Tetrahedron 2002, 58, 5927-5931.
doi:10.1016/S0040-4020(02)00534-3

[12]. Casiraghi, G.; Casnati, G.; Cornia, M. Tetrahedron Lett. 1973, 14, 679-682.
doi:10.1016/S0040-4039(00)72432-4

[13]. Casiraghi, G.; Casnati, G.; Catellani, M.; Cornia, M. Synthesis 1974, 564-564.
doi:10.1055/s-1974-23370

[14]. Jin, T. S.; Zhang, J. S.; Wang, A. Q.; Li, T. S. Synth. Commun. 2005, 35, 2339-2345.
doi:10.1080/00397910500187282

[15]. Hua, G. P.; Li, T. J.; Zhu, S. L.; Zhang, X. J. Chin. J. Org. Chem. 2005, 25(6), 716-719.

[16]. Jin, T. S.; Qi, N.; Li, M.; Han, L. S.; Liu, L. B.; Li, T. S. Asian. J. Chem. 2007, 19, 3803-3809.

[17]. Jin, T. S.; Zhang, J. S.; Xio, J.C.; Wang, A. Q.; Li, T. S. Synlett. 2004, 5, 866-870.
doi:10.1055/s-2004-820022

[18]. Khosropour, A. R.; Khodaei, M. M.; Moghannian, H. Synlett. 2005, 6, 955-958.
doi:10.1055/s-2005-864837

[19]. Das, B.; Thirupathi, P.; Ravinder Reddy, K.; Ravikanth, B.; Nagarapu, L. Catal. Commun. 2007, 8, 535-538.
doi:10.1016/j.catcom.2006.02.023

[20]. Das, B.; Thirupathi, P.; Mahender, I.; Reddy, V. S.; Rao. Y. K.; J. Mol. Catal. A: Chem. 2006, 247, 233-239.
doi:10.1016/j.molcata.2005.11.048

[21]. Shakibaei, G. I.; Mirzaei, P.; Bazgir, A. Appl. Catal. A: Gen. 2007, 325, 188-192.
doi:10.1016/j.apcata.2007.03.008

[22]. Dabiri, M.; Azimi, S. C.; Bazgir, A. Chem. Pap. 2008, 62, 522-526.
doi:10.2478/s11696-008-0050-y

[23]. Zhang, Z. H.; Tao, X. Y. Aus. J. Chem. 2008, 61, 77-79.

[24]. Li, J. J.; Tao, X. Y.; Zhang, Z. H. Phosphorus Sulfur. 2008, 183, 1672-1678.
doi:10.1080/10426500701724530

[25]. Song, G.; Wang, B.; Luo, H.; Yang, L. Catal. Commun. 2007, 8, 673-676.
doi:10.1016/j.catcom.2005.12.018

[26]. John, A.; Yadav, P.; J. P.; Palaniappan, S. J. Mol. Catal. A: Chem. 2006, 248, 121-125.
doi:10.1016/j.molcata.2005.12.017

[27]. Srihari, P.; Mandal, S.S.; Reddy, J.S.S.; Rao, R. S.; Yadav, J.S. Chin. Chem. Lett. 2008, 19, 771-774.
doi:10.1016/j.cclet.2008.05.005

[28]. Kantevari, S.; Bantu, R.; Nagarapu, L. J. Mol. Catal A: Chem. 2007, 269, 53-57.
doi:10.1016/j.molcata.2006.12.039

[29]. Lu, H. Y.; Li, J. J.; Zhang, Z. H. Appl. Organometal. Chem. 2009, 23, 165-169.
doi:10.1002/aoc.1488

[30]. Karthikeyana, G.; Pandurangana, A. J. Mol. Catal. A: Chem. 2009, 311, 36-45.
doi:10.1016/j.molcata.2009.06.020

[31]. Kumar, D.; Sandhu, J. S. Synth. Commun. 2010, 40, 510-517.
doi:10.1080/00397910902987792

[32]. Li, J.; Lu, L.; Su, W. Tetrahedron Lett. 2010, 51, 2434-2437.
doi:10.1016/j.tetlet.2010.02.149

[33]. Kang, H.; Hu, Y.; Huang, H.; Wei, P. Heterocycl. Commun. 2008, 14, 223-227.
doi:10.1515/HC.2008.14.4.223

[34]. Ma, J. J.; Wang, C.; Wu, Q. H.; Tang, R. X.; Liu, H. Y.; Li, Q. Heteroatom. Chem. 2008, 19, 609-611.
doi:10.1002/hc.20486

[35]. Fang, D.; Gong, K.; Liu, Z. L. Catal. Lett. 2009, 127, 291-295.
doi:10.1007/s10562-008-9677-0

[36]. Narender, M.; Reddy, M. S.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 5953-5955.
doi:10.1016/j.tetlet.2005.06.130

[37]. Reddy, M. S.; Narender, M.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 6437-6439.
doi:10.1016/j.tetlet.2005.07.114

[38]. Sridhar, R.; Srinivas, B.; Kumar, V. P.; Reddy, V. P.; Kumar, A. V.; Rao, K. R. Adv. Synth. Catal. 2008, 350, 1489-1492.
doi:10.1002/adsc.200800121

[39]. Madhav, B.; Murthy, S. N.; Reddy, V. P.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, 6025-6028.
doi:10.1016/j.tetlet.2009.08.033

[40]. Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron 2009, 65, 5251-5256.
doi:10.1016/j.tet.2009.04.081

[41]. Murthy, S. N.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3649-3653.
doi:10.1016/j.tetlet.2010.05.028

[42]. Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3938-3939.
doi:10.1016/j.tetlet.2010.05.096

[43]. Kirschner, D.; Jaramillo, M.; Green, T.; Hapiot, F.; Leclercq, L.; Bricout, H.; Monflier, E. J. Mol. Catal. A: Chem. 2008, 286, 11-20.
doi:10.1016/j.molcata.2008.01.038

[44]. Legrand, F. X.; Sauthier, M.; Flahaut, C.; Hachani, J.; Elfakir, C.; Fourmentin, S.; Tilloy, S.; Monflier, E. J. Mol. Catal. A: Chem. 2009, 300, 72-77.
doi:10.1016/j.molcata.2008.12.017

[45]. Six, N.; Menuel, S.; Bricout, H.; Hapiot, F.; Monflier, E. Adv. Synth. Catal. 2010, 352, 1467-1475.
doi:10.1002/adsc.201000027

[46]. Bricout, H.; Hapiot, F.; Ponchel, A.; Tilloy, S.; Monflier, E. Curr. Org. Chem. 2010, 14, 1296-1307.
doi:10.2174/138527210791616920

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