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






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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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Keywords


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

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DOI: 10.5155/eurjchem.2.3.300-307.358

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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. 30 Oct. 2020
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)

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

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