Water Extract of Onion Catalyzed Tandem CN and CC Bond Formation via Enaminone‐Michael Addition‐Intramolecular Cyclization: An Efficient Green Synthesis of Multi‐Substituted Pyrrole Derivatives and Their Antioxidant Activity

化学 迈克尔反应 串联 分子内力 催化作用 抗氧化剂 吡咯 药物化学 立体化学 组合化学 有机化学 复合材料 材料科学
作者
Selvaraj Loganathan,Rajendran Eswaran,Santhiya Ramasamy,M. Seenivasaperumal
出处
期刊:Journal of Heterocyclic Chemistry [Wiley]
标识
DOI:10.1002/jhet.70077
摘要

ABSTRACT An efficient tandem reaction method catalyzed by aqueous onion extract comprising enaminone formation followed by Michael addition‐cyclization is disclosed by 1,3‐diketone 1 , primary amine 2 , and β‐nitroalkene 3 . In this work, diverse structures of enaminones and β‐nitroalkenes 3 were involved to produce various multi‐substituted pyrroles 6 in excellent yields (up to 97%). The structure of compound 6d was confirmed by single‐crystal X‐ray diffraction. This method has been applicable for a broad range of substrates and good functional group tolerance. Further, this proposed methodology has added advantages such as a simple, short reaction time, easy workup procedure, and environmentally benign manner. The in vitro antioxidant activity studies of the produced compounds, 6a–6y , were examined. When compared to 6e–6g , 6l , 6m , 6q , 6r , 6t , and 6u , the compounds such as 6h , 6i , 6j , 6k , and 6x have shown excellent IC 50 value with standard (1.80 × 10 −4 M). In addition, compound 6h has demonstrated exceptional IC 50 value (1.58 × 10 −4 M) among the synthesized compounds.
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