Abstract
A simple, efficient and eco-friendly procedure for the synthesis of isoxazole derivatives (4a–4h) using one-pot three-component reaction between substituted aldehydes (1a), methyl acetoacetate (2a) and hydroxylamine hydrochloride (3a) has been achieved in presence of Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice respectively. The homogeneity of synthesized compounds was confirmed by melting point and thin layer chromatography. The synthesized compounds were characterized by using 1H NMR, FTIR and CHN analyses and evaluated for in vitro herbicidal activity against Raphanus sativus L. (Radish seeds). The compounds (4a–4h) were also screened for their fungicidal activity against Rhizoctonia solani and Colletotrichum gloeosporioides. Antibacterial activity was also tested against Erwinia carotovora and Xanthomonas citri. From bio-evaluation data, it was found that compound 4b was most active against Raphanus sativus L. (root) and Raphanus sativus L. (shoot) respectively. Compound 4b was also found most active against both the fungus viz. R. solani and C. gloeosporioides showing maximum percentage growth inhibition i.e. 90.00 against R. solani and 82.45 against C. gloeosporioides at 2000 µg/mL concentration. Compound 4 h has shown maximum inhibition zone i.e. 3.00–9.60 mm against Erwinia carotovora at 2000 µg/mL concentration. Maximum Xanthomonas citri growth was also inhibited by compound 4 h showing inhibition zone 1.00–5.00 mm at highest concentration.
Highlights
A simple, efficient and eco-friendly procedure for the synthesis of isoxazole derivatives (4a–4h) using one-pot three-component reaction between substituted aldehydes (1a), methyl acetoacetate (2a) and hydroxylamine hydrochloride (3a) has been achieved in presence of Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice respectively
Substituted aldehydes by use of catalytic amounts of sodium benzoate, sodium sulphide, sodium silicate, tartaric acid, pyridine, sodium ascorbate, sodium tetraborate and boric a cid[21]. These methods have some limitations such as harsh reaction conditions, expensive procedure, tedious work-up process, less product yield, less atom economy and completion of reaction time was more. Based on these findings and our on-going efforts towards synthesis of isoxazole derivatives, in this paper we reported one-pot three components clean and facile synthesis of isoxazole derivatives in presence of fruit juices viz. Cocos nucifera L. juice, Solanum lycopersi‐
We found that when the amount of Cocos nucifera L. juice was only 4.0 mL in reaction mixture yield of reaction was less
Summary
A simple, efficient and eco-friendly procedure for the synthesis of isoxazole derivatives (4a–4h) using one-pot three-component reaction between substituted aldehydes (1a), methyl acetoacetate (2a) and hydroxylamine hydrochloride (3a) has been achieved in presence of Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice respectively. The synthesized compounds were characterized by using 1H NMR, FTIR and CHN analyses and evaluated for in vitro herbicidal activity against Raphanus sativus L. From bio-evaluation data, it was found that compound 4b was most active against Raphanus sativus L. Compound 4b was found most active against both the fungus viz. R_solani and C. gloeosporioides showing maximum percentage growth inhibition i.e. 90.00 against R. solani and. Compound 4 h has shown maximum inhibition zone i.e. 3.00–9.60 mm against Erwinia carotovora at 2000 μg/mL concentration. Xanthomonas citri growth was inhibited by compound 4 h showing inhibition zone 1.00–5.00 mm at highest concentration. Multi-component reactions (MCRs) are important approach in organic chemistry in which a single operation is enough to form desired product from the well-defined condensation of three or more substrate m
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