A Review of Catalytic Innovations in the Synthesis of 1, 4-Dihydropyrano [2, 3-C] Pyrazoles via Four Component Method in the Last Decade
DOI:
https://doi.org/10.32628/IJSRST251222714Keywords:
Pyrano[2,3-c]pyrazole, four-component reaction, ethyl acetoacetate, one-pot synthesisAbstract
1,4-Dihydro Pyrano [2,3-c]pyrazole (1,4-DHPP) derivatives have many biological and medicinal properties hence received an interest by organic and medicinal chemists. Now a days multi-component reactions (MCRs) have been adopted for the synthesis of highly functionalized 1,4-dihydro pyrano[2,3-c] pyrazole derivatives as MCRs have its own importance in the field of chemistry and environment. . This review gives detail information about the methods used to synthesize 1,4-Dihydro Pyrano [2,3-c]pyrazole derivatives by one-pot four components over the last ten years. As compared with two components and three component methods four component condensation method is used in the greater extent by the researchers. This review also gives information about the different catalytic techniques and methods use for the synthesis of 1,4-DHPP.
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(a) B. Ganem, Acc. Chem. Res. 2009, 42, 463; (b) J. D. Sunderhaus, S. F. Martin, Chem. Eur. J., 2009, 15, 1300; (c) V. S. Satyanarayan, A. Shivkumar, Ultrason. Sonochem. 2011, 18, 917; (d) T. J. Mason Chem. Soc. Rev. 1997, 26, 443.
(a) M.C. Pirrung, Chem. Eur. J., 2006, 12, 1312; (b) S. Chitra, N. Paul, S. Muthusbramanian, P. Manisankar, Green Chem., 2011, 13, 2777; (c) U. M. Lindstrom, Organic reactions in water: Principles, Stratergies and Applications (Blackwell Publishing: Oxford, U.K.), 2007, p. 60; (d) C. J. Li, T. H. Chang, Comprehensive Organic reactions in aqueous media, 2nd Ed., (Jhon Wiley & Sons, Hoboken, New Jersey, U.S.A.), 2007, p. 2; (e) U. M. Lindstrom, Stereoselective organic reactions in water, Chem. Rev., 2002, 102, 2751; (f) N. R. Candeias, P. M. S. D. Cal, V. Andre, M. T. Duarte, L. F. Veiros, P. M. P. Gois, Tetrahedron, 2010, 66, 2736.
G. A. M. Nawwar, F. M. Abdelrazek, R. H. Swellam, Arch. Pharm. 1991, 324, 875.
M. E. A. Zaki, E. M. Morsy, F. M. A. Motti, F. M. E. A. Megeid, Heterocycl. Commun. 2004, 10, 97.
S. R. Mandha, S. Siliveri, M. Alla, V. R. Bommena, M. R. Bommineni, S. Balasubramanian, Bioorg. Med. Chem. Lett., 2012, 22, 5272.
E. S. E. Tamany, F. A. E. Sahed, B. H. Mohamed, J. Serb. Chem. Soc. 1999, 64, 9.
S. A. E. Assiery, G. H. Sayed, A. Founda, Acta Pharma., 2004, 54, 143.
P. T. Mistry, N. R. Kamdar, D. D. Haveliwala, S. K. Patel, J. Heterocycl. Chem. 2012, 49, 349.
H. Junek, H. Aigner, Chem. Ber., 1973, 106, 914.
H. H. Otto, Arch. Pharm, 1974, 307, 444.
Y. A. Sharanian, L. G. Sharanina, V. V. Puzanova, J. Org. Chem. USSR, (Engl. Transl.), 1983, 2291.
A. S. Waghmare, S .S. Pandit, DABCO Catalyzed rapid one-pot synthesis of 1,4-dihydropyrano [2,3-c] pyrazole derivatives in aqueous media, J. Saudi Chem. Soc., 2017, 21, 286-290.
M. Seydiment, K. Ablajan, M. Hamdulla, W. Li, A. Omar, M. Obul, L-proline catalyzed four component one-pot synthesis of coumarin containing dihydropyrano[2,3-c]pyrazoles under ultrasonic irradiation, Tetrahedron, 2016, 72, 7599-7605.
A.R. Moosavi-Zare, M.A. Zolfigol, A. Mousavi-Tashar, Synthesis of pyranopyrazole derivatives by in situ generation of trityl cabocation under mild and neutral media, Res. Chem. Intermed., 2016, 42, 7305-7312.
A.R. Moosavi-Zare, M.A. Zolfigol, R. Salehi-Moratab, E. Noroozizadeh, Catalytic application of 1-(carboxymethyl)-pyridinium iodide on the synthesis of pyranopyrazole derivatives, Mol. Catal. Chem., 2016, 415, 144-150.
I. A. Khodja, A. Fisli, O. Lebhour, R. Boulcina, B. Boudjemaa, A. Debache, Four component synthesis of pyrano[2,3-c]pyrazoles catalyzed by triphenylphosphine in aqueous medium. LOC, 2016, 13, 85-91.
M.S. Narayana, S. Maddila, W.E. VanZyl, S.B. Jonnalagadda, Ru-Hydroxyapatite: An efficient and reusable catalyst for the multicomponent synthesis of Pyranopyrazoles under facile green conditions, COS, 2016, 13, 893-900.
J. Davarpanah, R. Khoram, Synthesis of pyranopyrazole compounds using heterogeneous base catalyst based on 1,3,5-trizine-2,4,6-triamine modified nano rice husk silica, J. Nanoanalysis, 2017, 4, 20-30.
B. Pati Tripathi, A. Mishra, P. Rai, Y. Kumar Pandey, M. Srivastava, S. Yadav, J. Singh, A green and clean pathay: One pot, multicomponent and visible light assisted synthesis of pyrano[2,3-c]pyrazoles under catalyst-free and solvent-free conditions, New J. Chem., 2017, 41, 11148-11154.
S.N. Maddila, S. Maddila, W. E. Van-Zye, S. B. Jonnalagadda, CeO2/ZrO2 as green catalyst for one-pot synthesis of new pyrano[2,3-c]pyrazoles, Res. Chem. Intermed, 2017, 43, 4313-4325
V. N. Bhosale, G. S. Khansole, J. A. Angular, S. S. Choudhare, A.R. Karad, N.B. Wadwale, One pot four component synthesis of pyranopyrazole derivatives using TBAHS as green catalyst and their biological evaluation, Asian J. Res. Chem., 2017, 10, 745.
V. L. Gein, T. M. Zamaraeva, P. A. Slepukhin, Diethyl oxaloacetate sodium salts as a reagent to obtain functionalized spiro[indoline-3,4-pyrano[2,3-c]pyrazoles] Tetrahedron Lett., 2017, 58, 134-136.
B.D. Rupnar, V. P. Pagore, S. U. Tekale, S. U. Shisodia, R.P. Pawar, L-tyrosine catalyzed mild and efficient synthesis of dihydropyrano[2,3-c]pyrazoles under microwave irradiation, Der Chem. Sin., 2017, 7, 229-234.
M. G. Dehbalaei, N. Foroughifar, H. Pasdar, A. Khaieh-Amiri, N. Foroughifar, M. Alikarami, Choline Chloride based thoiurea catalyzed highly efficient eco-friendly synthesis and anti-bacterial evaluation of some new 6-amino-4-aryl-2,4-dihydro-3-phenyl pyrano[2,3-c] pyrazole-5-carbonitrile derivatives, Res. Chem. Intermed., 2017, 43, 3035-3051.
K. K. Gangu, S. Maddila, S. N. Maddila, S. B. Jonnalagadda, Novel iorn doped calcium oxalates as promising heterogeneous catalysts for one-pot multi-component synthesis of pyranopyrazoles, RSC Advances, 2017, 7, 423-432
P. Farokhian, M. Mamaghani, N. O. Mahmoodi, K. Tabatabaeian, A green and practical method for the synthesis of novel pyrano[2,3-c]pyrazoles and bis- pyrano[2,3-c]pyrazoles usning sulfonic acid-functionalized ionic liquid, J. Iran. Chem. Soc., 2018, 15, 11-16.
R. H. Vekariya, K. D. Patel, H. D. Patel, An efficient protocol for the one-pot four component synthesis of 6-amino 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives using starch solution as a reaction media. Indian J. Chem., 2018, 57B, 576-582.
M. Beerappa, K. Shivashankar, Four component synthesis of highly functionalized pyrano[2,3-c] pyrazoles from benzyl halides, Synth. Commun, 2018, 48, 146-154.
Z. Halizadeh, A. Maleki, Poly(ethylene imine)-modified magnetic hallosite nanotubes: A novel, efficient and recyclable catalyst for the synthesis of dihydropyrano[2,3-c] pyrazole derivatives, Mol. Catal., 2018, 460, 87-93.
S.V. H. S. Bhaskaruni, S. Maddila, .E. VanZyl, S.B. Jonnalagadda, An efficient and green approach for the synthesis of 2,4-dihydropyrano[2,3-c] pyrazole-3-carboxylates using Bi2O3/ZrO2 as a reusable catalyst. RSC Advances, 2018, 8, 16336-16343.
P. Singh, M. Kumar, M. A. Quraishi, J. Haque, G. Singh, Bispyranopyrazoles as green corrosion inhibitors for mild steel hydrochloricn acid: experimenetal and theoretical approach, ACS, Omega, 2018, 3, 11151-11162.
S. Maddila, S. Gorle, S. Shabalala, O. Oyetade, S. N. Maddila, P. Lavanya, S. B. Jonnalagadda, Ultrasound mediated green synthesis of synthesis of pyrano[2,3-c] pyrazole by using Mn doped ZrO2, Arab. J. Chem., 2019, 12, 671-679.
Y. Chen, Z, Zhang, W. Jiang, M. Zhang, Y. Li, RuIII@CMC/Fe3O4 hybrid: an efficienmt magnetic, retrievable self-organized nanocatalyst for green synthesis of pyranopyrazoel and polyhydroquinoline derivatives, Mol. Divers., 2019, 23, 421-442
A. R. Moosavi-Zare, H. Afshar-Hezarkhani, M. M. Rezaei, Tandem four component condensation reaction of aryl aldehydes with ethylacetoacetate, malanonitrile and hydrazine hydrate using boric acid in water as an efficient and green catalytic system, Polycycl. Aromat. Compd., 2020, 40, 150-158.
S. Sikandar, A. F. Zahoor, S. Ahmad, M. N. Anjum, M. N. Ahmad, M. S. U. Shah, L-cysteine catalyzed environmentally benign one-pot multicomponent approach towards the synthesis of dihydropyrano[2,3-c]pyrazole derivatives, Curr. Org. Synth., 2020, 17, 457-463.
P. Shrivas, R. Pandey, S. Zodape, A. ankhade, U. Pratap, Green synthesis of pyranopyrazoles via biocatalytic one –piot knoevenagel condensation Michael type addition heterocyclization cascade non-aqueousn media, Res. Chem. Intermed., 2020, 46, 2805-2816.
M. N. Hosseini, M. Gholizadeh, Nano silica extracted from horsetail plant as a neutral silica support for the synthesis of H3PW12O40 immobilized on laminated magnetic nanoparticles (Fe3O4@SiO2-EP-NH-HPA): a novel and efficient heterogeneous nanocatalyst for the green one-pot synthesis of pyrano[2,3-c] pyrazole derivatives. Res. Chem. Intermed., 2020, 46, 3037-3066.
H. Faroughi Niva, N. Hazeri, M. T. Maghsoodlou, Synthesis and characterization of Fe3O4@THAM-SO3H as a highly reusable nanocatalyst and its application for the synthesis of dihydropyrano[2,3-c] pyrazole derivatives, Appl. Organomet. Chem., 2020, 34, e5472.
P. Chattise, S. Saleh, V. Pandit, S. Arbuj, V. Chabuksar, ZnO nanostructures: A heterogeneous catalyst for the synthesis of benzoxanthene and pyranopyrazole scaffolds via a multi-component reaction strategy, Mater. Adv., 2020, 1, 2339-2345.
E. Babaei, B.B. F. Mirijalili, An expedient and eco-friendly approach for multicomponent synthesis of dihydropyrano[2,3-c] pyrazoles using nano-Al2O3/BF3/Fe3O4 as reusable catalyst, Inorg. Nano-Met. Chem., 2020, 50, 16-21.
M. Mehravar, B. F. Mirjalili, E. Babaei, A. Bamoniri, Preparation and application of nano-AlPO4/ Ti(IV) as a new and recyclable catalyst for the four-component synthesis of dihydropyrano[2,3-c] pyrazoles, Polycycl. Aromat. Compd., 2020, 1-10.
S. Babaees, M. Zarei, H. Sepehramansourie, M. A. Zolfigol, S. Rostamnia, Synthesis of metal-organic frameworks MIL-101 (Cr)-NH2 containing phosphorous acid functional groups: Applicaion for the synthesis of n-amino-2-pyridone and pyrano[2,3-c] pyrazole derivatives via a cooperative vinylogous anomeric-based oxidation, ACS Omega, 2020, 5, 6240-6249.
A.D. Tafti, B.B. F. Mirjalili, A. Bamoniri, N. Salehi, Rapid four-component synthesis of dihydropyrano[2,3-c] pyrazoles using nano-eggshell/Ti(IV) a highly compatible natural based catalyst, BMC Chem., 2021, 15, 6.
H. T. Nguyen, M. N. H. Truong, T. V. Le, N. T. Vo, H. D. Nguyen, P. H. Tran, A new pathway for the preparation of pyrano[2,3-c] pyrazoles and molecular docking as inhibitors of p38 MAP Kinase.
K. kalpana, V. A. Rani, A. Ranga, R. Perumandala, R. Ramani, One-pot synthesis of 6-amino-4-(furan/thiophenyl/pyrrol-2-yl)-3-methyl-1,4-dihydropyrano[2,3-c] pyrazole-5-carbonitriles, Evaluation of anticancer activity and molecular modeling studies. Russ. J. Gen. Chem., 2023, 93, 128-135
F. Heyadri, M. Bakhtiarian, M. M. Khodaei, Preparation of Fe3O4@Carrageenam-Metformin nanoparticles as a new bio inspired magnetic nanoparticles for the synthesis of dihydropyrano[2,3-c] pyrazoles. Mater. Sci. Eng. B. 2023, 296, 116686.
D. Mallah, B.B.F. Mirjalili, A green protocol ball milling synthesis of dihydropyrano[2,3-c] pyrazole using nano-silica/aminoethylpiperazine as a metal-free catalyst. BMC Chem., 2023, 17, 10.
M. Darabi, M. Nikoorazm, B. Tahmasbi, A. GhorbaniChoghamarani, Immonilization of Ni(II) complex on the surface of mesoporous modified-KIT-6 as a new, reusable and highly effficent nanocatalyst for the synthesis of tetrazole and pyranopyrazle derivatives. RSC Adv. 2023, 13, 12572-12588.
A. K. Pandey, K. Mishra, S. C. Shrivastava, P. Shukla, A. Tripathi One-pot, multicomponent synthesis of dihydropyrano[2,3-c] pyrazoles catalyzed by preheated Fly-ash in aqueous medium, J. Sci. Islam. Repub. Iran 2023, 34, 129-136.
F. Mohamadpour H. Kamyab, S. Chelliapan, A. M. Amani, Synthesis of dihydropyrano[2,3-c] pyrazole scaffolds by methylene blue (MB+) as photo-redox catalyst via a single-electron transfer (SET)/energy transfer (EnT) pathay. Curr. Res. Green Sustain. Chem., 2023, 7, 100381.
A.P. Katariya, M.V. Kataria, J. Sangshetti, S. U. Deshmukh Ionic Liquid [(EMIM)Ac] catalyzed green and efficient synthesis of pyrano[2,3-c] pyrazole, Polycycl. Aromat. Compd., 2023, 43, 3761
New protocol as used by Cetin and Bayden in which DL-alpha-tocopherol methoxypolyethylene glycol succinate solution acts as a biodegadable catalyst for the synthesis of pyrano[2,3-c] pyrazoles.
S. Fuse, B. Sonane, B. Madje, Ultrasonic mediated synthesis of dihydropyrano[2,3-c] pyrazolen derivatives catalyzed by Cyanuric acid/1-methyl imidazole, Int. J. Sci. Res. Sci. Tech., 2024, 11, 238-243.
A. Mobinikhaledi, N. Ahadi, M. Taati, The green synthesis of pyranopyrazole derivatives by silica supported cobalt chloride and cobalt nitrate as nanocatalyst, Collid Nano J. 2025, 2, 419-432.
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