Abstract
New and facile one-pot three component approach for the synthesis of substituted dihydropyrimidinones derivatives (4a-4h) from reaction of equimolar substituted aldehydes (1a-1h), methyl acetoacetate (2a) and urea (3a) in presence of nature derived catalyst viz. Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice, commonly known as coconut juice, tomato juice and musambi juice respectively, at room temperature has been carried out. All synthesized compounds were evaluated for in vitro herbicidal activity against Raphanus sativus L. (Radish seeds). The compounds (4a-4h) were also screened for their antifungal activity against Rhizoctonia solani and Colletotrichum gloeosporioides by poisoned food techniques method. Antibacterial activity was also studied against Erwinia cartovora and Xanthomonas citri by inhibition zone method. From activity data, it was found that compounds 4g and 4d were most active against Raphanus sativus L. (root) and Raphanus sativus L. (shoot) respectively. Compounds 4f and 4c was found most active against Rhizoctonia solani and Colletotrichum gloeosporioides fungus respectively at highest concentration. Compound 4g has shown maximum inhibition zone i.e. 1.00-5.50 mm against Erwinia cartovora at 2000 μg/mL concentration. Maximum Xanthomonas citrii growth was inhibited by compounds 4f showing inhibition zone 4.00-12.00 mm at highest concentration. Short reaction time, high yields, mild reaction condition and simple work-up are some merits of present methodology.
Highlights
Dihyropyrimidinones and its derivatives are found in a large family of natural products with wide biological activities, due to which they become important class of heterocyclic compounds
We reported the synthesis of substituted dihydropyrimidinones (4a-4h) by one-pot multicomponent reaction between equimolar substituted aldehydes (1a-1h) viz. 2-Hydroxybenzaldehyde (1a), 4-Methoxybenzaldehyde (1b), 3,4-Dimethoxybenzaldehyde (1c), 4-Chlorobenzaldehyde (1d), 4-Bromobenzaldehyde (1e), 3-Hydroxybenzaldehyde (1f), Scheme 1
The reaction conditions were optimized by performing the reaction between 4-Hydroxy3-methoxybenzaldehyde (20 mmol), methyl acetoacetate (20 mmol) and urea (20 mmol) in presence of catalyst viz. Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice at room temperature
Summary
Dihyropyrimidinones and its derivatives are found in a large family of natural products with wide biological activities, due to which they become important class of heterocyclic compounds. They generally possess therapeutic and pharmacological properties [1] and several derivatives of dihydropyrimidinone acts as calcium channel modulators [2], Ca-antagonists and vasodilative and antihypertensive [3]. In this paper we reported one-pot three components clean and facile synthesis of dihydropyrimidinone derivative in presence of fruit juices viz. Cocos nucifera L., Solanum lycopersicum L., Citrus limetta respectively.
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