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A Facile One-Pot Synthesis of 3-Methylbenzisoxazoles via a Key Intermediate of ortho-Ethoxyvinyl Nitroaryls by Domino Rearrangement and Their Anti- Inflammatory Activity

Author(s):

Bethanamudi Prasanna*, Nagaraju B, Shanmukha kumar J.V , Nareshvarma Seelam and T. Subbaiah   Pages 1 - 5 ( 5 )

Abstract:


Background: Recently, there has been a lot of scientific interest in exploring the syntheses of oxygen and nitrogen containing heterocyclic compounds due to their pharmacological activities. In addition, benzisoxazoles play very important role in organic synthesis as key intermediates.

Objective: In this paper, we focused on developing novel synthetic route for biologically active arylisoxazoles under normal conditions, simplified it to get high purities and yields, and also reported their anti-inflammatory activities.

Method: An efficient and simple method has been explored for the synthesis of novel 3-methyl arylisoxazoles from o-nitroaryl halides via o-ethoxyvinylnitroaryls, using dihydrated stannous chloride (SnCl2.2H2O) in MeOH / EtOAc (1:1) via Domino rearrangement in one pot.

Result: We synthesized novel 3-methylarylisoxazoles from o-nitroarylhalides via o-ethoxyvinylnitroaryls, using dihydrated stannous chloride (SnCl2.2H2O) in MeOH / EtOAc (1:1) via domino rearrangement. In this reduction nitro group and ethoxy vinyl group changed to the functionality of acyl ketones, followed by hetero cyclization takes place. Here, the reaction proceeds without isolation of intermediates like 2-acylnitroarenes and 2-acylanilines. All the synthesized compounds were completely characterized by the NMR and mass spectra. The compounds were also explored anti-inflammatory activity using carrageenan induced inflammation in the albino rats (150-200 g) of either sex were used in this entire study with Diclofenac sodium was used as standard drug. The initial evaluations identified very lead targets with good to moderate anti-inflammatory activity.

Conclusion: A simple, one-pot and convenient method has been explored for the synthesis of novel 3-methylarylisoxazoles with high purity and reaction yields. All the compounds 3a, 3c, 3d, 3f, 3g and 3h exhibited 51-64% anti-inflammatory activities.

Keywords:

Arylisoxazoles, Domino rearrangement, SnCl2.2H2O, Anti-inflammatory activities, o-Ethoxyvinyl nitro aryls, Diclofenac.

Affiliation:

Department of Chemistry, Chaitanya Postgraduate College (Autonomous), Kishanpura, Hanamkonda, Warangal, Telangana State-506001., Department of Chemistry, Chaitanya Postgraduate College (Autonomous), Kishanpura, Hanamkonda, Warangal, Telangana State-506001., Research& Development, Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur (A.P) 522502, Research& Development, Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur (A.P) 522502, Research& Development, Department of Chemistry, Koneru Lakshmaiah Education Foundation, Guntur (A.P) 522502



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