European Journal of Chemistry

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

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Published: Jun 30, 2011
DOI: https://doi.org/10.5155/eurjchem.2.2.272-275.359
Keywords:
β-Cyclodextrin, Condensation, Aromatic aldehydes, 1, 3-Cyclohexanedione, 5, 5-Dimethyl-1, 3-cyclohexanedione, Water
Section
Short Communication
Issue
Vol. 2 No. 2 (2011): June 2011
Dates
Received 2010-12-02
Accepted 2010-12-16
Published 2011-06-30


Main Article Content

Swapna Kokkirala
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
Narayana Murthy Sabbavarapu
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
Venkata Durga Nageswar Yadavalli
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

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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