One-pot three component synthesis of substituted dihydropyrimidinones using fruit juices as biocatalyst and their biological studies

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.

From traditional to greener alternatives: potential of plant resources as a biotransformation tool in organic synthesis

“…In light of the increasing significance of N-heterocycles, the Biginelli reaction was tested by employing a variety of bioresources ranging from Citrus maxima to coconut water and baker's yeast. [35][36][37][38][39][40][41][42][43][44][45] The reaction is often catalyzed by acids, but metals have been shown to catalyse the production of several bio-catalyst media. From Table 1, it was quite obvious that in the synthesis of 5-acetyl-4-(4-methoxyphenyl)-3,4dihydropyrimidin-2-(1H)-one, using bio-catalysts based on natural acids and enzymes can drive the reaction even under mild conditions, providing good yield compared to commonly used organic and inorganic catalysts like p-TsOH, RuCl 3 , etc.…”

Bio Inspired CdO Nanoparticles: A Robust and Recyclable Catalyst Towards the Synthesis of Dihydropyrimidone Derivatives via One Pot Three‐Component Coupling Reaction

“…[1,2] Such reactions have garnered substantial importance within the realm of organic synthesis due to their atomic and energetic efficiency, making them highly advantageous compared to linear organic synthesis approaches in terms of their applications within the fields of organic chemistry and pharmacology. [3][4][5] Amongst these, the Biginelli reaction stands out as one of the most versatile multicomponent reactions (MCRs), [6][7][8][9][10] with its products finding significant relevance in diverse biological activities, including anticancer, [11] antimicrobial and therapeutic agents, [12,13] anti-inflammatory, antibacterial, and antifungal agents. [14] Contemporary requirements demand the synthesis of various nanoparticles for myriad applications.…”

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

“…The synthetic method initially reported by Biginelli has undergone changes, such as the “Atwal-modification” [ 4 , 5 ], and most often, the most efficient catalyst has been sought, which would lead to a higher product yield, milder reaction conditions, and efficient catalyst recovery [ 16 , 17 ]. In the last decade, several improved methods were reported for the Biginelli synthesis of these compounds, including solvent free synthesis [ 18 ], ultrasound radiation [ 19 ], microwave irradiation [ 20 ], visible light irradiation [ 21 ], or using a biocatalyst [ 22 ]. Further methods include using various catalysts, such as Bronsted acids, including H 3 BO 3 [ 15 ], HCOOH [ 21 ], p-TsOH-H 2 O [ 23 , 24 ], imidazole-1–yl-acetic acid [ 25 ], and L-(+)-tartaric acid-dimethylurea [ 26 ]; or Lewis acids, including LiClO 4 , Lal 3 , InCl 3 , BiCl 3 , Bi(OTf) 3 , Mn(OAc) 3 , Cu(OTf) 2 , CuCl 2 , FeCl 3 , ZrCl 4 , SnCl 2 , [ 27 , 28 , 29 , 30 , 31 , 32 ], Sr(OTf) 2 [ 33 ], VCl 3 [ 34 ], TaBr 5 [ 35 ], Ce(NO 3 ) 3 ·6H 2 O [ 36 ], ZrO 2 /SO 4 2− [ 37 ], silica-chloride (SiO 2 -Cl) [ 38 ], Sm(ClO 4 ) 3 [ 39 ], Y(NO 3 ) 3 ·6H 2 O [ 40 ], CeCl 3· 7H 2 O [ 41 ], Ce(NH 4 ) 2 (NO 3 ) 6 (CAN) [ 42 ], Fe(OTs) 3· 6H 2 O [ 43 ], Ca(HSO 4 ) 2 , Zn(HSO 4 ) 2 [ 44 ], SnCl 2 /nano SiO 2 [ …”