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Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions
Parikibanda Venkata Ramana (1)
, Annadi Ram Reddy (2,*) (1) Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007, India
(2) Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007, India
(*) Corresponding Author
Received: 02 Dec 2010 | Revised: 08 Jan 2011 | Accepted: 27 Jan 2011 | Published: 30 Sep 2011 | Issue Date: September 2011
Abstract
The synthesis of series of 3-aryl-4-dihydrooxazolyl-5-methyl trisubstituted isoxazoles (VI) is reported, both under thermal and microwave conditions starting from various benzaldehydes (I). Benzaldehydes undergo oximation with hydroxylamine hydrosulphate to provide oximes that upon chlorination, followed by condensation with methylacetoacetate, resulted in the formation of esters. Hydrolysis of the esters to acids followed by treatment with PCl5, resulted in the formation of acid chlorides (III) that upon reaction with hydroxyamines, gave N-β-hydoxyalkyl amides (IV). These on further reaction with SOCl2, followed by cyclization with 2 N NaOH provided oxazoline substituted isoxazoles (VI) in good yields. The conversion acid chlorides (III) to isoxazoles (VI) was also achieved by microwave irradiation in moderate to excellent yields, with shorter reaction times compared to the conventional thermal method.
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DOI: 10.5155/eurjchem.2.3.300-307.358
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References
[1]. Santos, M. M. M.; Natalia, F.; Jim, I.; Simon, C. J.; Michael, H. B.; Martins, M. L.; Rui, M. Bioorg. Med. Chem. Lett. 2010, 20, 193-195.
http://dx.doi.org/10.1016/j.bmcl.2009.10.137
[2]. Reddy, C. S.; Nagaraj, A. Heterocycl. Commun. 2008, 14, 289-294.
http://dx.doi.org/10.1515/HC.2008.14.4.289
[3]. Al-Omran, F.; El-Khair, A. A. J. Heterocycl. Chem. 2005, 42, 307-312.
http://dx.doi.org/10.1002/jhet.5570420222
[4]. Hikmet, A.; Selahaddin, G.; Fatma, B.; Sema, K.; Fatma, K.; Nathaly, S.; Vasyl, K.; Anatholy, D. Bioorg. Med. Chem. 2007, 15, 2322-2333.
http://dx.doi.org/10.1016/j.bmc.2007.01.029
[5]. Patrizia, C.; Lars, N.; Seema, M.; Anders, H. Bioorg. Med. Chem. Lett. 2004, 14, 5997-6000.
http://dx.doi.org/10.1016/j.bmcl.2004.09.087
[6]. Banerjee, M.; Azam, M. A.; Sahu, S. K. J. Chem. Pharm. Sci. 2009, 2, 35-37.
[7]. Karabasanagouda, T.; Vasudeva, A. A.; Girisha, M. Indian J. Chem., Sect. B 2009, 48B, 430-437.
[8]. Subash, V.; Michael, B.; Reaz, U.; Baojie, W.; Scott, F. G.; Pavel, P. A. J. Med. Chem. 2008, 51, 1999-2002.
http://dx.doi.org/10.1021/jm701372r
PMid:18335974
[9]. Tao, L.; Xiaowu, D.; Na, X.; Rui, W.; Qiaojun, H.; Bo, Y.; Yongzhou, H. Bioorg. Med. Chem. 2009, 17, 6279-6285.
http://dx.doi.org/10.1016/j.bmc.2009.07.040
[10]. Taek, H. Y.; Kyung, K. E.; Ae, K. E.; Seon, K. E.; Kyong, K. D.; Young-Ger, S.; Hoon, M. K. Bull. Korean Chem. Soc. 2009, 30, 779-780.
http://dx.doi.org/10.5012/bkcs.2009.30.4.779
[11]. Zhang, C.-Y.; Bao-Lei, W.; Xing-Hai, L.; Yong-Hong, L.; Su-Hua, W.; Zheng-Ming, L. Heterocycl. Commun. 2008, 14, 397-404.
http://dx.doi.org/10.1515/HC.2008.14.6.397
[12]. Yu-Xiu, L.; Zhi-Peng, C.; Bin, L.; Bao-Li, C.; Yong-Hong, L.; Qing-Min, W. J. Agric. Food Chem. 2010, 58, 2685-2689.
http://dx.doi.org/10.1021/jf902541w
PMid:20000686
[13]. Yu-Han, Z.; Rong, M. W.; Bai, C. L. Chin. Chem. Lett. 2003, 14, 897-900.
[14]. Soni, A. K.; Krupadanam, G. L. D.; Srimannarayana, G. Arkivoc, 2006, 16, 35-42.
[15]. Egan, J. A.; Nugent, R. P.; Filer, C. N. J. Radioanal. Nucl. Chem. 2009, 279, 935-936.
http://dx.doi.org/10.1007/s10967-008-7381-6
[16]. Victor, K. E.; Anatoly, A. G.; Muratov, E. N.; Volineckaya, I. L.; Makarov, V. A.; Olga, R. B.; Peter, W.; Michaela, S. J. Med. Chem. 2007, 50, 4205- 4213.
http://dx.doi.org/10.1021/jm0704806
PMid:17665898
[17]. Yoon-Suk, L.; Byeang, H. K. Bioorg. Med. Chem. Lett. 2002, 12, 1395-1397.
http://dx.doi.org/10.1016/S0960-894X(02)00182-8
[18]. Ryng, S.; Gtowiak, T. J. Chem. Crystallogr. 1998, 28, 373-378.
http://dx.doi.org/10.1023/A:1022464225693
[19]. Liu, B.; Liu, G.; Xin, Z.; Serby, M. D.; Zhao, H.; Schaefer, V. G.; Falls, H. D.; Kaszubska, W.; Collins, C. A.; Sham, H. L. Bioorg. Med. chem. Lett. 2004, 14, 5223-5226.
http://dx.doi.org/10.1016/j.bmcl.2004.06.060
[20]. Gordon, C. G.; Charles, E. R.; Robert, G. A.; Hilary, J. A. Tetrahedron Lett. 2006, 47, 2245-2247.
http://dx.doi.org/10.1016/j.tetlet.2006.01.089
[21]. Sunel, V.; Ciovica, S.; Asandei, N.; Soldea, C. Cell. Chem. Technol. 1995, 29, 11-15.
[22]. Jacques, B. J.; Isabelle, F.; Christian, J.; Michel, L.; Alain, C. Arch. Pharm. 1994, 327, 187-192.
http://dx.doi.org/10.1002/ardp.19943270311
PMid:8179477
[23]. Ara, K. S.; Fatima, K. N.; Shashikanth, M. Bioorg. Med. Chem. Lett. 2008, 18, 4597-4601.
http://dx.doi.org/10.1016/j.bmcl.2008.07.029
[24]. Padmavathi, V.; Reddy, K. M.; Dinneswara, G.; Padmaja, A. Eur. J. Med. Chem. 2010, 45, 3178-3183.
http://dx.doi.org/10.1016/j.ejmech.2010.04.010
PMid:20444528
[25]. Rameshwar U. K; Archana, C.; Nilanjan, R. Bioorg . Med. Chem. Lett. 2007, 17, 861-868.
http://dx.doi.org/10.1016/j.bmcl.2006.11.069
[26]. Mikko, M. J.; Heikki, K.; Antti, K. O.; Maija, L. K.; Susanna, S. M.; Antti, P.; Koskinen, A. M. P. Eur. J. Med. Chem. 2009, 44, 4179-4191.
http://dx.doi.org/10.1016/j.ejmech.2009.05.012
PMid:19539407
[27]. Kunal, R.; Somnath, P. QSAR Comb. Sci. 2009, 28, 406-425.
http://dx.doi.org/10.1002/qsar.200810130
[28]. Markus, H.; Sebastian, W.; Alexander, S.; Florian, P.; Peter, K.; Oliver, R. Tetrahedron: Asym. 2010, 21, 1194-1198.
http://dx.doi.org/10.1016/j.tetasy.2010.03.030
[29]. Keisuke, K.; Satoshi, M.; Tomoyuki, M.; Takuya, K.; Hiroyuki, A. Angew. Chem. Int. Ed. Engl. 2009, 48, 3326-3328.
http://dx.doi.org/10.1002/anie.200806080
PMid:19191366
[30]. Mazuela, J.; Verendel, J. J.; Mercedes, C.; Schaffner, B.; Borner, A.; Andersson, P. G.; Pamies, O.; Dieguez, M. J. Am. Chem. Soc. 2009, 131, 12344-12353.
http://dx.doi.org/10.1021/ja904152r
PMid:19658416
[31]. Yasuhiro, I.; Nobumasa, A.; Miki, H.; Toshihiro, H.; Rikako, K. WO 037271, 2005, Chem. Abstr. 142, 430265.
[32]. Nelson, J. K.; Burns, T. C.; Smith, P. M.; Twamley, B.; Natale, N.R. Tetrahedron Lett. 2008, 49, 3078-3082.
http://dx.doi.org/10.1016/j.tetlet.2008.03.059
PMid:21103024 PMCid:2988249
[33]. Zhi-wei, C.; Wei-hua, Y.; Wei-ke, S. Zhongguo Xiandai Yingyong Yaoxue 2008, 25, 308-309, Chem. Abstr. 150, 539604.
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DOI Link: https://doi.org/10.5155/eurjchem.2.3.300-307.358
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