MICROWAVE IRRADIATED GREEN BIGINELLI REACTION” EMPLOYING APPLE, POMEGRANATE AND GRAPE JUICE AS ECO-FRIENDLY REACTION MEDIUM

Authors

  • Tanay Pramanik Department of Chemistry, Faculty of Technology and Sciences, Lovely Professional University, Phagwara, P.O.Box 144411, India
  • Simarjit Kaur Padan

Abstract

Objective: The main objective of this work is to explore the utility of apple, pomegranate and grape juice as an eco-friendly reaction medium for microwave assisted green Biginelli reaction.

Methods: A series of Biginelli reactions were carried out in various fruit juice medium by employing an equimolar mixture of urea, ethyl acetoacetate and aromatic aldehyde as reactants. All the reactions were performed with the help of microwave irradiation. After successful completion of the reactions, the crude products were isolated, and the pure products were obtained after recrystallization of the crude product from hot ethanol.

Results: It was worth to note that all the reactions were completed successfully within few minutes of duration. Pure apple, pomegranate and grape juices were proved to be fruitful as eco-friendly reaction medium for performing microwave-assisted green Biginelli reaction.

Conclusion: A green, eco-friendly and cost-effective method was developed for microwave assisted green Biginelli reaction†in apple, pomegranate and grape juice medium. This new method will further motivate the researchers to use more of common fruit juices instead of toxic solvents as reaction medium for multi-component condensation reactions.

Keywords: Green synthesis, Fruit Juice, Biginelli reaction, Microwave

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References

Kappe CO. Recent advances in the biginelli dihydropyridine synthesis. New Tricks from an old dog. Acc Chem Res 2000;33:879−88.

Sakata KI, Someya M, Matsumoto Y, Tauchi H, Kai M, Toyota M, et al. Gimeracil, an inhibitor of dihydropyridine dehydrogenase, inhibits the early step in homologous recombination. Cancer Sci 2011;102:1712−6.

Ramesh B, Bhalgat CM. Novel dihydropyrimidines and its pyrazole derivatives: Synthesis and pharmacological screening. Eur J Med Chem 2011;46:1882−91.

Zhu L, Cheng P, Lei N, Yao J, Sheng C, Zhuang C, et al. Synthesis and biological evaluation of novel homo camptothecins conjugating with dihydropyridine derivatives as potent topoisomerase I inhibitors. Arch Pharm Chem Life Sci 2011;344:726−34.

Biginelli P. Aldureides of ethylic acetoacetate and ethylic oxalacetate. Gazz Chim Ital 1893;23:360-416.

Hu EH, Sidler DR, Dolling UH. Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-Alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones. J Org Chem 1998;63:3454-7.

Lu J, Ma H. Iron(III)-Catalyzed synthesis of dihydropyrimidinones. Improved Conditions for the Biginelli Reaction. Synlett; 2000. p. 63-4.

Ranu BC, Hajra A, Jana U. Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the biginelli reaction. J Org Chem 2000;65:6270-2.

Ramalinga K, Vijayalakshmi P, Kaimal TNB. Bismuth(III)-catalyzed synthesis of dihydropyrimidinases: improved protocol conditions for the biginelli reaction. Synlett 2001;6:863-5.

Lu J, Bai Y, Wang Z, Yang B, Ma H. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett 2000;41:9075-8.

Yadav JS, Reddy BVS, Srinivas R, Venugopal C, Ramalingam T. LiClO4-catalyzed one-pot synthesis of dihydropyrimidinones: improved protocol for Biginelli reaction. Synthesis 2001;9:1341-5.

Kumar KA, Kasthuraiah M, Reddy CS, Reddy CD. Mn(OAc)3•2H2O-mediated three-component, one-pot,condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones. Tetrahedron Lett 2001;42:7873-5.

Yadav JS, Reddy BVS, Reddy KB, Raj KS, Prasad AR. Ultrasound-accelerated synthesis of 3, 4-dihydropyrimidin-2 (1 H)-ones with ceric ammonium nitrate. J Chem Soc Perkin Trans 2001;1:1939-41.

Pramanik T, Wani TA, Singh A. Influence of electronic factors on Solvent-Free and catalyst free biginelli reactionâ€. Orient J Chem 2013;29:1209-12.

Pramanik T, Pathan AH. Exploring the utility of fruit juices as a green medium for biginelli reaction. Res J Pharm Biol Chem Sci 2014;5:444-9.

Pramanik T, Pathan AH, Gupta R, Singh J, Singh S. Dihydropyrimidinone derivatives: green synthesis and effect of an electronic factor on their antimicrobial properties. Res J Pharm Biol Chem Sci 2015;6:1152-7.

Pramanik T, Maji P. Microwave assisted green synthesis of pharmaceutically important dihydropyrimidinones in fruit juice medium. Int J Pharm Pharm Sci 2015;7:376-9.

Mingoes D. Chem Ind; 1994. p. 596-9.

Bose AK, Pednekar SN, Ganguly S, Chakraborty GM, Manhas S. A simplified green chemistry approach to the Biginelli reaction using ‘Grindstone Chemistry’. Tetrahedron Lett 2004; 45:8351-3.

Baskaran SS, Koenig B. Efficient synthesis of 3,4-dihydropyrimidin-2-ones in low melting tartaric acid–urea mixtures. Green Chem 2011;13:1009-13.

Fu NY, Yuan YF, Zhong C, Wang S, Wang T, Peppe C. Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Tetrahedron 2002;58:4801-7.

Published

01-03-2016

How to Cite

Pramanik, T., and S. K. Padan. “MICROWAVE IRRADIATED GREEN BIGINELLI REACTION” EMPLOYING APPLE, POMEGRANATE AND GRAPE JUICE AS ECO-FRIENDLY REACTION MEDIUM”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, no. 3, Mar. 2016, pp. 396-8, https://www.innovareacademics.in/journals/index.php/ijpps/article/view/10525.

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Short Communication(s)