European Journal of Chemistry 2011, 2(3), 300-307 | doi: https://doi.org/10.5155/eurjchem.2.3.300-307.358 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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.

2_3_300_307_800


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Isoxazole; Ethanolamine; Microwave irradiation; Dihydrooxazoline; Conventional; Oximation

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.3.300-307.358

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1311 times | icon graph PDF Article downloaded 591 times


Citations

/


[1]. Hardik G. Bhatt, Yadvendra K. Agrawal, Manish J. Patel
Amino- and fluoro-substituted quinoline-4-carboxylic acid derivatives: MWI synthesis, cytotoxic activity, apoptotic DNA fragmentation and molecular docking studies
Medicinal Chemistry Research  24(4), 1662, 2015
DOI: 10.1007/s00044-014-1248-x
/


[2]. Hardik Bhatt, Paresh Patel, Christophe Pannecouque
Discovery of HIV-1 Integrase Inhibitors: Pharmacophore Mapping, Virtual Screening, Molecular Docking, Synthesis, and Biological Evaluation
Chemical Biology & Drug Design  83(2), 154, 2014
DOI: 10.1111/cbdd.12207
/


[3]. Vasubabu Gorantla, Rambabu Gundla, Surender Singh Jadav, Sreenivasa Reddy Anugu, Jithendra Chimakurthy, Kameswara Rao NS, Raghubabu Korupolu
New Anti-Inflammatory HybridN-Acyl Hydrazone-Linked Isoxazole Derivatives as COX-2 Inhibitors:Rational Design, Synthesis and Biological Evaluation
ChemistrySelect  2(26), 8091, 2017
DOI: 10.1002/slct.201701421
/


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.


How to cite


Ramana, P.; Reddy, A. Eur. J. Chem. 2011, 2(3), 300-307. doi:10.5155/eurjchem.2.3.300-307.358
Ramana, P.; Reddy, A. Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions. Eur. J. Chem. 2011, 2(3), 300-307. doi:10.5155/eurjchem.2.3.300-307.358
Ramana, P., & Reddy, A. (2011). Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions. European Journal of Chemistry, 2(3), 300-307. doi:10.5155/eurjchem.2.3.300-307.358
Ramana, Parikibanda, & Annadi Ram Reddy. "Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions." European Journal of Chemistry [Online], 2.3 (2011): 300-307. Web. 4 Jun. 2023
Ramana, Parikibanda, AND Reddy, Annadi. "Synthesis of dihydrooxazoylarylisoxazoles by conventional and under microwave conditions" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.2.3.300-307.358


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2011, 2(3), 300-307 | doi: https://doi.org/10.5155/eurjchem.2.3.300-307.358 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.