Document Type : Original Paper
Authors
- Arvind Kumar Pandey 1
- Kuldeep Mishra 2
- Subhash Chandra Shrivastava 1
- Poonam Shukla 1
- Ashutosh Tripathi 3
1 1 Department of Chemistry, University of Allahabad, Prayagraj, UP-211002, India
2 2 Department of Chemistry, CMP Degree College, Prayagraj (A constituent PG college of Unversity of Allahabad, Prayagraj) UP-211002, India
3 3 K.S. Saket P.G. College, A Government-Aided PG college of DR RML Avadh University, Ayodhya, UP-224123, India
Abstract
A facile one-pot multicomponent protocol for the synthesis of bio-active dihydropyrano(2,3-c)pyrazole derivatives from ethyl acetoacetate, hydrazine hydrate, malononitrile and aryl aldehydes using preheated-fly-ash as catalyst for the first time.These environmentally begin multicomponent cyclocondensations offer some interesting advantages, advantages of this methodology are the use of nontoxic solvent, cost-effective and easy availability of catalyst, ease of the work-up, high yields (up to 95%), and green protocol.
Keywords
Main Subjects
- Gu Y. Multicomponent reactions in unconventional solvents: state of the art. Green Chem. 2012;14:2091-2118.
- Kanchithalaivan S, Sivakumar S, Ranjith Kumar R, Elumalai P, Ahmed QN and Padala AK. Four Component Domino Strategy for the Combinatorial Synthesis of Novel 1,4-Dihydropyrano[2,3 c]pyrazol-6-amines. ACS Combinat Sci. 2013;15(12):631-638.
- Sunderhaus JD and Martin SF. Applications of Multicomponent Reactions to the Synthesis of Diverse Heterocyclic Scaffolds. Chemistry (Weinheiman der Bergstrasse, Germany). 2009;15(6):1300-1308.
- Brauch S, van Berkel SS and Westermann B. Higher-order multicomponent reactions: beyond four reactants. Chem Soc Rev. 2013;42(12):4948-4962.
- Naim MJ, Alam O, Farah Nawaz M, Alam J and Alam P. Current status of pyrazole and its biological activities. J Pharm BioAllied Sci. 2016;8(1):2-17.
- Ganta RK, Kerru N, Maddila S and Jonnalagadda SB. Molecules. 2021;26:3270-3301.
- Al-Amiery AA, Al-Bayati RI, Saed FM, Ali WB, Kadhum AAH and Mohamad AB. Novel Pyranopyrazoles: Synthesis and Theoretical Studies. Molecules. 2012;17:10377-10389.
- Zolfigol MA, Tavasoli M, Moosavi-Zare AR, Moosavi P, Kruger HG, Shiri M and Khakyzadeh V. Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst. RSC Adv. 2013;3:25681-25685.
- Smith RH, Jorgensen WL, Tirado-Rives J, Lamb ML, Janssen PA, Michejda CJ and Kroeger Smith MB. Prediction of Binding Affinities for TIBO Inhibitors of HIV-1 Reverse Transcriptase Using Monte Carlo Simulations in a Linear Response Method. J Med Chem. 1998;41(26):5272-5286.
- Wang JL, Liu D, Zhang Z, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES and Huang Z, Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proceed Natl Acad Sci. 2000;97(13):7124-7129.
- Kuo SC, Huang LJ, and Nakamura H. Studies on Heterocyclic Compounds 6. Synthesis and Analgesic and Antiinflammatory Activities of 3,4-Dimethylpyrano[2,3-c]pyrazol-6-one Derivatives. J Med Chem. 1984;27(4):539-544.
- Chougala BM, Samundeeswari S, Holiyachi M, Shastri LA, Dodamani S, Jalalpure S and Sunagar VA. Synthesis, characterization and molecular docking studies of substituted 4- coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and antiinflammatory agents. Eur j med chem. 2017;125:101-116.
- Colotta V, Catarzi D, Varano F, Melani F, Filacchioni G, Cecchi L, Trincavelli L, Martini C and Lucacchini A. Synthesis and A1 and A2A adenosine binding activity of some pyrano [ 2,3-c ] pyrazol-4-ones. IL Farmaco. 1998;53:189-196.
- Zhang CY, Liu XH, Wang BL, Wang SH and Li ZM. Synthesis and Antifungal Activities of New Pyrazole Derivatives via 1,3-dipolar Cycloaddition Reaction. Chem Biol Drug Design. 2010;75(5):489-493.
- Saha A, Payra S and Banerjee S. One-pot multicomponent synthesis of highly functionalized bio-active pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives using ZrO2 nanoparticles as a reusable catalyst. Green Chem. 2015;17(5):2859-2866.
- Ebrahimi J, Mohammadi A, Pakjoo V, Bahramzade E and Habibi A. Highly efficient solvent-free synthesis of pyranopyrazoles by a Brønsted-acidic ionic liquid as a green and reusable catalyst. J Chem Sci. 2012;124(5):1013-1017.
- Valiey E, Dekamin MG and Alirezvani Z. Melamine-modified chitosan materials: An efficient and recyclable bifunctional organocatalyst for green synthesis of densely functionalized bioactive dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives. Int J Biol Macromol. 2019;129:407-421.
- Maddila SN, Maddila S, Werner, E. van Zyl and Sreekantha BJ. CeO2/ZrO2 as green catalyst for one-pot synthesis of new pyrano[2,3-c]-pyrazoles. Res Chem Intermed. 2017;43:4313-4325.
- Saha M and Pal AK. Palladium (0) Nanoparticles: A Novel and Reusable Catalyst for the Synthesis of Various Pyran Derivatives. Adv Nanoparticles. 2012;1(3):61-70.
- Guo SB, Wang SX and Li JT. D,L‐Proline‐Catalyzed One‐Pot Synthesis of Pyrans and Pyrano[2,3‐c]pyrazole Derivatives by a Grinding Method under Solvent‐Free Conditions. Synthet Commun. 2007;3713:2111-2120.
- Liu T, Lai YH, Yu YQ and Xu DZ. A facile and efficient procedure for one-pot four-component synthesis of polysubstituted spiro pyrano[2,3-c]pyrazole and spiro 1,4-dihydropyridine catalyzed by Dabco-based ionic liquid under mild condition. New J Chem. 2018;42(2):1046-1051.
- Fatahpour M, Sadeh FN, Hazeri, Maghsoodlou MT, Hadavi MS and Mahnaei S. Ag/TiO2 nano-thin films as robust heterogeneous catalyst for one-pot, multi-component synthesis of bis (pyrazol-5-ol) and dihydropyrano [2,3-c] pyrazole analogs. J Saudi Chem Soc. 2017;21(8):998-1006.
- Pradhan K, Paul S and Das AR. Magnetically retrievable nano crystalline CuFe2O4 catalyzed multi-component reaction: a facile and efficient synthesis of functionalized dihydropyrano [2,3-c] pyrazole, pyrano [3, 2-c] coumarin and 4 H-chromene derivatives in aqueous media. Catalys Sci Technol. 2014;4(3):822-831.
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- Mali G, Shaikh BA, Garg S, Kumar A, Bhattacharyya S, Erande R and Chate AV. Design, Synthesis, and Biological Evaluation of Densely Substituted Dihydropyrano [2,3-c] pyrazoles via a Taurine-Catalyzed Green Multicomponent Approach. ACS Omega. 2021;6(45):30734-30742.
- Thirunarayanan G and Sekar KG. Preheated fly-ash catalyzed cyclization ofchalcones: Synthesis of some substituted pyrazole-1-carbothioamides and spectral correlations in 3-(3, 4-dichlorophenyl)-5-(substituted phenyl)-4, 5-dihydro-1H-pyrazole-1 carbothioamides. Int Lett Chem Physics Astronomy. 2013;10:18-34.
- A.K .Pandey, A. Kumar, P. Singh and S. K. Srivastava. Activated fly-ash promoted cost effective and green synthesis of hexahydroacridine-1,8(2H,5H)-diones in aqueous medium. Heterocycl Lett. 2021;11(4):675-682.
- Arulkumaran R, Vijayakumar S, Sakthinathan SP, Kamalakkannan D, Ranganathan K, Suresh R, Sundararajan R, Vanangamudi G and Thirunarayanan G. Preheated FLY-ASH catalyzed aldol condensation: efficient synthesis of chalcones and antimicrobial activities of some 3-thienyl chalcones. J Chil Chem Soc. 2013;58(2):1684-1690.
- Tafti A, Mirjalili BF, Bamoniri A and Salehi N. Rapid four-component synthesis of dihydropyrano[2,3-c]pyrazoles using nano-eggshell/Ti(IV) as a highly compatible natural based catalyst. BMC Chem. 2021;15(1):1-8.
- Pandey AK, Kumar and Shrivastava SC. Sugarcane Bagasse Ash-Based Silica-Supported Boric Acid (SBA-SiO2-H3BO3): A Versatile and Reusable Catalyst for the Synthesis of 1, 4Dihydropyrano [2,3-c] pyrazole Derivatives. Russian J Organ Chem. 2021;57(4):653-660.
- Mishra M, Nizam A, Jomon KJ and Tadaparthi K. A New Facile Ultrasound-Assisted Magnetic Nano-[CoFe2O4]-Catalyzed One-Pot Synthesis of Pyrano [2, 3-c] pyrazoles. Russian J Organ Chem. 2019;55(12):1925-1928.
- Kiyani H, Samimi H, Ghorbani F and Esmaieli S. One-pot, four-component synthesis of pyrano [2,3-c] pyrazoles catalyzed by sodium benzoate in aqueous medium. Curr Chem Lett. 2013;2(4):197-206.
- Shahbazi S, Ghasemzadeh MA, Shakib P, Zolfaghari MR and Bahmani M. Synthesis and antimicrobial study of 1, 4-dihydropyrano [2, 3-c] pyrazole derivatives in the presence of amino-functionalized silica-coated cobalt oxide nanostructures as catalyst. Polyhedron. 2019;170:172-179.
- Mohamadpour F. Catalyst-free green synthesis of dihydropyrano[2,3-c]pyrazole scaffolds assisted by ethylene glycol (E-G) as a reusable and biodegradable solvent medium. J Chem Sci. 2020;132(1):72-80.
- Shrivas P, Pandey R, Zodape S, Wankhade A and Pratap U. Green synthesis of pyranopyrazoles via biocatalytic one-pot Knoevenagel condensation–Michael-type addition–heterocyclization cascade in non-aqueous media. Res Chem Intermed. 2020;46(5):2805-2816.
35. Reddy GM, Kumari AK, Reddy VH and Garcia JR. Novel pyranopyrazole derivatives comprising a benzoxazole core as antimicrobial inhibitors: Design, synthesis, microbial resistance and machine aided results. Bioorgan Chem.
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