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A Microwave Accelerated Sustainable Approach for the Synthesis of 2-amino-4H-chromenes Catalysed by WEPPA: A Green Strategy

[ Vol. 6 , Issue. 1 ]

Author(s):

Prashant B. Hiremath and Kantharaju Kamanna*   Pages 30 - 43 ( 14 )

Abstract:


Background: The agricultural wastes as a source offer an excellent alternative to replace many toxic and environmentally hazardous catalysts, due to their least toxicity, ease of biodegradability, and ability to act as a greener catalytic medium. Some of the agro-waste based catalysts reported are BFE, WERSA, WEB, and WEPBA. 2-Amino-4H-chromene derivatives are promising biologically potent heterocyclic compounds, due to their medicinal applications such as antimicrobial, anti-inflammatory, antibacterial, antiviral, anticancer, antidiuretic, anticoagulant and antianaphylactic activities. The present work describes a microwave accelerated, efficient, eco-friendly and economical approach for the synthesis of 2-amino-4H-chromenes through condensation of substituted arylaldehyde, malononitrile and resorcinol/naphthol catalyzed water extract of pomegranate peel ash (WEPPA) under microwave irradiation. The reaction completed within 3-6 min with good to excellent yield of product isolation. The final product isolated by simple filtration and recrystallization gave a spectroscopically pure form of product and did not require further purification.

Methods: The pomegranate peel ash water extract as an agro-waste derived catalyst was employed under microwave irradiation for the economical synthesis of 2-amino-4H-chromene derivatives.

Results: The reported agro-waste based catalyst was obtained in the absence of external base, additives and solvent-free synthesis of 2-amino-4H-chromene using aryl aldehyde, malononitrile and resorcinol/ naphthol under microwave irradiation. WEPPA acts as a solvent media and catalyst, as it plays a dual role in the synthesis of 2-amino-4H-chromenes.

Conclusion: We established an efficient, simple, agro-waste based catalytic approach for the synthesis of 2-amino-4H-chromene derivatives from the condensation of arylaldehyde, malononitrile and resorcinol/α-naphthol/β-naphthol employing WEPPA as an efficient catalyst under microwave synthesis. The method has found to be a greener, economic and eco-friendly approach for the synthesis of chromene scaffolds. The advantages of the present approach are solvent-free, no external metal, chemical base free, short reaction time and isolated product in good to excellent yields. The catalyst is agro-waste derived, which has abundant natural sources available, thus making the present approach a greener one.

Keywords:

Agro-waste, green catalyst, Green chemistry, 2-amino-4H-chromenes, arylaldehyde, malononitrile, resorcinol, microwave accelerated.

Affiliation:

Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, P-B, NH-4, Belagavi 591156, Karnataka, Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, P-B, NH-4, Belagavi 591156, Karnataka

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