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Abstract
An environmentally benign synthesis of pyranopyrazoles derivatives has been developed by a four-component reaction between aldehyde, malononitrile, hydrazine hydrate and ethyl acetoacetate in the presence of ammonium chloride in water medium. This method follows the principle of green chemistry by using environmentally benign synthetic method along with use of ammonium chloride as a catalyst and green reaction medium. All the derivatives were evaluated for antimicrobial screening against two Gram-negative bacteria, two Gram-positive bacteria and three fungal species. Among all the tested compounds, it was found that compounds N-3, N-4 and N-9 revealed better activity against the Gram-positive rather than the Gram-negative bacteria.
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References
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References
H. Adibi, L. Hosseinzadeh, S. Farhadi and F. Ahmadi, Synthesis and Cytotoxic Evaluation of 6-Amino-4-aryl-3-methyl-2,4-dihydropyrano-[2,3-c]pyrazole-carbonitrile Derivatives using Borax with Potential Anticancer Effects, J. Reports Pharma. Sci., 2, 116 (2013).
E.S. El-Tamany, F.A. El-Shahed and B.H. Mohamed, Synthesis and Biological Activity of Some Pyrazole Derivatives, J. Serb. Chem. Soc., 64, 9 (1999).
M.E.A. Zaki, H.A. Saliman and O.A. Hiekal, Pyrazolopyranopyrimi-dines as a Class of Anti-Inflammatory Agents, Z. Naturforsch. C: Biosci., 61, 1 (2006).
P.M. Khandare, R.D. Ingale, A.S. Taware, S.U. Shisodia, S.S. Pawar, L. Kotai and R.P. Pawar, One Pot Synthesis and Biological Evaluation of Pyranopyrazole in Aqueous Medium, Eur. Chem. Bull., 6, 410 (2017) https://doi.org/10.17628/ecb.2017.6.410-414
F.M. Abdelrazek, P. Metz, N.H. Metwally and S.F. El-Mahrouky, Synthesis and Molluscicidal Activity of New Cinnoline and Pyrano-[2,3-c]pyrazole Derivatives, Arch. Pharm., 339, 456 (2006); https://doi.org/10.1002/ardp.200600057
H. Junek and H. Aigner, Synthesen mit Nitrilen, XXXV. Reaktionen von Tetracyanäthylen mit Heterocyclen, Chem. Ber., 106, 914 (1973); https://doi.org/10.1002/cber.19731060323
H. Wamhoff, E. Kroth and K. Strauch, Dihalogentriphenylphosphorane in der Heterocyclensynthese; 271: Heterokondensierte 1,2,4-Triazolo-[1,5-c]pyrimidine aus Enaminonitrilen via o-Ethylformimide, Synthesis, 1129 (1993); https://doi.org/10.1055/s-1993-26014
G. Tacconi, G. Gatti, G. Desimoni and V. Messori, A New Route to 4H-Pyrano[2,3-c]pyrazoles, J. Prakt. Chem., 322, 831 (1980); https://doi.org/10.1002/prac.19803220519
L.G. Sharanina, V.P. Marshtupa and A.S. Yu, Synthesis of 6-Amino-5-cyano-1H,4H-pyrazolo[3,4-b]pyrans, Khim. Geterosikl. Soedin, 10, 1420 (1980).
Yu.A. Sharanin, L.G. Sharanina and V.V. Puzanova, Nitrile Cyclization Reactions. VII. Synthesis of 6-Amino-4-aryl-3-methyl-5-cyano-1H,4H-pyrazolo[3,4-b]pyrans, Zh. Org. Khim., 19, 2609 (1983).
A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova and D.H. Evans, Cross-Condensation of Derivatives of Cyanoacetic Acid and Carbonyl Compounds. Part 1: Single-Stage Synthesis of 1¢-Substituted 6-Amino-spiro-4-(piperidine-4¢)-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles, Tetrahedron, 59, 7491 (2003); https://doi.org/10.1016/S0040-4020(03)01178-5
A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova and D.H. Evans, One-Step Synthesis of Substituted 6-Amino-5-cyanospiro-4-(piperidine-4¢)- 2H,4H-dihydropyrazolo[3,4-b]pyrans, Org. Lett., 4, 423 (2002); https://doi.org/10.1021/ol0102747
Y. Peng, G. Song and R. Dou, Surface Cleaning under Combined Microwave and Ultrasound Irradiation: Flash Synthesis of 4H-pyrano-[2,3-c]pyrazoles in Aqueous Media, Green Chem., 8, 573 (2006); https://doi.org/10.1039/b601209d
A.I. Vogel’s Textbook of Practical Organic Chemistry, ELBS, Longman Scientific and Technical: England, edn 5, p. 1150 (1994).
National Committee for Clinical and Laboratory Standards, Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, NCCLS, Villanova, Italy, edn 4, Document M 100-S7-S100-S157 (1997).