Green synthesis of pyranopyrazole using microwave assisted techniques

Abhinav Bais; Dinesh Chaple; Alpana Asnani; Pratyush Kumar; Shrikant Mohurle

doi:10.30574/gscbps.2020.10.2.0026

Authors

Abhinav Bais Priyadarshini J. L. College of Pharmacy, Electronic zone, Electronic building, Hingna Road, Nagpur-440016 (Maharashtra), (India).
Dinesh Chaple Priyadarshini J. L. College of Pharmacy, Electronic zone, Electronic building, Hingna Road, Nagpur-440016 (Maharashtra), (India).
Alpana Asnani Priyadarshini J. L. College of Pharmacy, Electronic zone, Electronic building, Hingna Road, Nagpur-440016 (Maharashtra), (India).
Pratyush Kumar Priyadarshini J. L. College of Pharmacy, Electronic zone, Electronic building, Hingna Road, Nagpur-440016 (Maharashtra), (India).
Shrikant Mohurle Priyadarshini J. L. College of Pharmacy, Electronic zone, Electronic building, Hingna Road, Nagpur-440016 (Maharashtra), (India).

DOI:

https://doi.org/10.30574/gscbps.2020.10.2.0026

Keywords:

Drug discovery, Pyranopyrazole, Microwave irridation, Green synthesis, Biological activity.

Abstract

The process of drug discovery involves the identification of lead molecule, synthesis, characterization, screening, assay for therapeutic efficacy. The Pyrano[2,3-c] pyrazole are important roles in the field of pharmacological and medicinal chemistry. The pyranopyrazole are important class of hetrocyclic ring prepared by a diverse range of synthetic procedure. The water as a green solvent is most enviormentally friendly, safe and inexpensive choice to decrese pollution, toxicity and cost of reaction. The Microwave irridation to eliminate the requirement of heat, enhance the rate of reaction and decreased total time is a widely applicable techinque and has been used for the synthesis of pyranopyrazole. The synthesis prepared by pyrazolone, aldehyde and malononitrile are allowed to react together under diffrent reaction condition to form a variety of pyranopyrazoles. The Pyranopyrazoles in general are biologically active and have remarkable antimicrobial, anticancer, anti-inflammatory, analgesic, antifungal etc.

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References

Christian GD. (2006). Analytical Chemistry, Fifth edition, John Wiley and Sons, Singapore, 340.

Pozharskii Af, Sodatemkov At and Kartritzky Ar. (1997). Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, Second Edition, 6(4), 301.

Jug K, Oricine Dc and Katritzky Ar. (2001). Quantitative Measures of Aromaticity for Mono-, Bi-, and Tricyclic Penta and Hexaatomic Hetero aromatic Ring Systems and Their Interrelationships, Chemistry Review, (101), 1421-1450.

Elnagdi Mh, Elmoghayar Mrh and Sadek Ku. (1987).Chemistry of Pyrazolopyrimidines, Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt. Advance Heterocyclic Chemistry, 41, 314.

Elnagdi Mh, Elmoghayar Mrh and Sadek. Ku. (1990). Chemistry of Pyrazolopyrimidines, Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt. Advance Heterocyclic Chemistry, 48, 223.

Abdelrazek FM, Metz P, Jäger A and Metwally NH. (2017). An Eco-friendly Synthesis of Some Novel 4-methyl-4-hetaryl Chromene and Pyrano[2,3-c ]pyrazole Derivatives. Journal of Heterocyclic Chemistry, 54 (4), 2313–2318.

Junek H and Aigner H. (1973). Reaktionen von Tetracyanathylen rnit Heterocyclen, Institute for Organic Chemistry, Graz, A-8010. Flemrichstr, Chemische Berichte, 106, 914-921.

Otto HH. (1974). Diversity Oriented Synthesis of Pyrano[2,3-c]pyrazoles and their Characterization. Arch Pharm Chemistry of Life Science, 307(6), 444-447.

Fustero S, Sánchez-Roselló M, Barrio P and Simón-Fuentes A. (2011). From 2000 to Mid-2010: A fruitful decade for the synthesis of pyrazoles. Chemical Reviews, Acs Publication, 111, 6984–7034.

Ansari A, Ali A and Asif M. (2017). Biologically active Pyrazole Derivatives. New Journal of Chemistry, 41, 16–41.

Myrboh B, Mecadon H, Rohman M, Rajbangshi M, Kharkongor I, Laloo B, Kharbangar I and Kshiar B. (2013). Organic Preparation and Procedures International Journal for Organic Synthesis, 45(4), 253-303.

Fadda A, El-Mekabaty A and Elattar K. (2013). Chemistry of Enaminonitriles of pyrano[2,3-c]pyrazole and Realated compound. An International Journal for Rapid Communication of Synthetic Organic Chemistry, 43(20), 2685-2719.

Stolle R. (1905). Ueber die Cozdensation von Acetessigoater mit Phengl-methyl-pyrazolon und die Einwirkungsproducte von Phenylhydrazin und Hydrazin auf Dehydracetsaure. European Journal of Organic Chemistry, 38(3), 3023-3032.

Wolff L. (1905). Ueber das Azin des Aceteasigesters. European Journal of Organic Chemistry, 38(3), 3036-3041.

Junek H and Aigner H. (1973). Synthesen mit Nitrilen, Reaktionen von Tetracyanäthylen mit Heterocyclen. Journal of CHEMISCHE BERICHET, 106(3), 914-921.

Khan MA, Cosenza AG and Ellis GP. (1982). Synthesis and Reactions of 1H, 6H-pyrano [2, 3-c]pyrazole-6-ones. Journal of Heterocyclic Chemistry, 19, 1077-1085.

Khan MA, Ellis GP and Pagotto MC. (2001). Pyranopyrazoles III Synthesis of 1H-Pyrano [2, 3-c]pyrazol-4-ones. Journal of Heterocyclic Chemistry, 38(1), 193-197.

Otto HH. (1974). Diversity Oriented Synthesis of Pyrano [2,3-c]pyrazoles and their Characterization. Arch Pharm Chemistry of Life Science, 307(6), 444-447.

Wang J, Huang GB, Yang LJ, Li F, Nie J and Maa JA. (2015). Tandem Stereoselective Synthesis of New Trifluoromethylated Pyranopyrazoles. Journal of Fluorine Chemistry, 171, 27- 35.

Smith R. (2006).Superheated water: the ultimate green solvent for separation science. Analytical and Bioanalytical Chemistry, 385(3), 419-421.

Peng Y, Song G and Dou R. (2006). Surface cleaning under combined microwave and ultrasound irradiation: flash synthesis of 4H-pyrano [2, 3-c]pyrazoles in aqueous media. Journal of Green Chemistry, 8(6), 573-575.

Abdou S, Fahmy SM, Sadek KU and Elnagdi. (1981). Activated nitriles in heterocyclic synthesis: a novel synthesis of pyrano [2, 3-c~pyrazoles. An International Journal for Reviews and Communications in Heterocyclic Chemistry, 16(12), 2177 - 2180.

Jin TS, Zhao RQ and Li TS. (2006). An one-pot three-component process for the synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1, 4-dihydropyrano [2,3-c]pyrazoles in aqueous media. Archive for Organic Chemistry, 11, 176-182.

Jin TS, Wang AQ, Cheng ZL, Zhang JS and Li TS. (2005). A Clean and simple synthesis of 6-Amino-4-Aryl-5-cyno-3-methyl-1-phenyl-1, 4-dihydropyrano[2,3-c]pyrazole in water. An International Journal for Rapid Communication of Synthetic Organic Chemistry, 35(1), 137-143.

Prajapati SP, Patel DP and Patel PS. (2012). Phenylboronic acid-catalyzed a four component synthesis of pyrano[2,3-c] pyrazole derivatives in aqueous media: an eco-friendly method . Journal of Chemical and Pharmaceutical Research, 4, 2652-2655.

Yu C, Yao C, Li T and Wang, X. (2014). An aqueous, catalyst-free and three-component synthesis of 6-amino-3-(trifluoromethyl)-1,4-dihydro1-phenyl-4-arylpyrano[2,3-c]pyrazole-5-carbonitriles. Research on Chemical Intermediates, 40(4), 1537-1544.

Bhavanarushi S, Kanakaiah V, Yakaiah E, Saddanapu V, Addlagatta A and Rani. (2013). Synthesis, cytotoxic, and DNA binding studies of novel fluorinated condensed pyrano pyrazoles. Journal Medicinal Chemistry Research, 22(5), 2446-2454.

Zhou JF, Tu SJ and Zhu HQ Zhi. (2002). a facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation. An International Journal for Rapid Communication of Synthetic Organic Chemistry, 32, 3363-3366.

Katariya LK and Kharadi GJ. (2014). A Facile One Post Synthesis of Pyrano[2,3-c] Pyrazoles with Implement of Various Basic Catalysts and its Biological Evaluation. International Journal for Pharmaceutical Research Scholars, 3, 627-637.