This study reports the development of a novel substituted hydrazone prepared from 2-hydroxy-4,5-dimethylacetophenone and hydrazine in alkaline medium at controlled conditions which yields as corresponding hydrazone [(E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol]. The structure of synthesized (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol was elucidated by elemental analysis and spectroscopic techniques like infrared spectroscopy, ultraviolet–visible spectroscopy, high-performance liquid chromatography, proton nuclear magnetic resonance and mass spectrum.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Tax calculation will be finalised during checkout.
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
Tax calculation will be finalised during checkout.
Hooda J. 2012 Review of biological activities of hydrazones Indonesian J. Pharm. 23 193
Turan-Zitouni G, Blache Y and Güven K 2001 Synthesis and antimicrobial activity of some imidazo-[1,2-a]pyridine-2- carboxylic acid arylidenehydrazide derivatives Boll. Chim. Farm. 140 397
Singh N, Ranjana R, Kumari M and Kumar B 2016 A review on biological activities of hydrazone derivatives Int. J. Pharm. Clin. Res. 8 162
Mohammed S J and Zuhair F G 2017 Synthesis of some bis-hydrazones derived from benzilic acid hydrazide and study antibacterial activity J. Chem. 1 1
Gao P and Wei Y 2013 Efficient oxidative cyclization of N–acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions Heterocycl. Commun. 19 113
Yadagiri P, Sailu B, Sunitha P, Ramesh Reddy A, Ram B and Balram B 2014 Synthesis and antibacterial activity of novel (E)-N′-((2-(Naphthalen-8-yl) phenyl)methylene)Benzohydrazide derivatives J. Appl. Chem. 3 1488
Ghoneim A A and Assy M G 2015 Synthesis and characterization of antimicrobial activity of azoles and azines derivatives from tertiary butyl carbazate Org. Chem. Curr. Res. 4 148
Al-Ajely H M Synthesis of some 4-oxobenzotriazolo hydrazones Am. Res. J. Chem. 1 11
Kumaran P M, Mangayarkarasi V, Parasuraman P, Bhagyalakshmi S, Vamsi K K and Shireesha N 2013 Synthesis and biological evaluation of hydrazone derivatives Asian J. Pharm. Anal. Med. Chem. 1 104
Gunjan J and Awadh D 2011 Synthesis and biological evaluation of hydrazone derivatives Int. Res. J. Pharm. 2 110
Rehman S.-Ur, Ikram M, Rehman S, Islam N U and Jan N 2011 Synthesis and characterization of Ni(II), Cu(II) and Zn(II) tetrahedral transition metal complexes of modified hydrazine J. Mex. Chem. Soc. 55 164
Verma G, Marella A, Shaquiquzzaman M, Akhtar M, Ali M R and Alam M M 2014 A review exploring biological activities of hydrazones J. Pharm. Bioallied Sci. 6 69
Sarkar S, Siddiqui A A, Saha S J, De R, Mazumder S, Banerjee C, Iqbal M S, Nag S, Susanta Adhikari S and Bandyopadhyay U 2016 Antimalarial activity of small-molecule benzothiazole hydrazones Am. Soc. Microbiol. Antimicrob. Agents Chem. 60 4217
Al-Saadawy N H 2017 Preparation and Characterization of novel metal complexes containing hydrazone derived from camphor and 2,4-dinitrophenyl hydrazine Res. J. Chem. Sci. 7 16
Govindasami T, Pandey A, Palanivelu N and Pandey A 2011 Synthesis, characterization and antibacterial activity of biologically important vanillin related hydrazone derivatives Int. J. Org. Chem. 1 71
Mohareb R M, El-Sharkawy K A, Hussein M M and El-Sehrawi H M 2010 Synthesis of hydrazide-hydrazone derivatives and their evaluation of antidepressant, sedative and analgesic agents J. Pharm. Sci. Res. 2 185
Sondhi S M, Dinodia M and Kumar A 2006 Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives Bioorg. Med. Chem. 14 4657
Todeschini Adriane R, de Miranda A L P, da Silva K C M, Parrini S C and Barreiro E J 1998 Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives Eur. J. Med. Chem. 33 189
Popiolek L 2017 Hydrazide–hydrazones as potential antimicrobial agents: overview of the literature since 2010 Med. Chem. Res. 26 287
Bharti S K, Nath G, Tilak R and Singh S K 2010 Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring Eur. J. Med. Chem. 45 651
Özdemir A, Turan-zitouni G, Kaplancikli Z A, Demirci F and Iscan G 2008 Studies on hydrazone derivatives as antifungal agents J. Enzyme Inhib. Med. Chem. 23 470
Popiołek L and Biernasiuk A 2017 Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety Saudi Pharm. J. 25 1097.
Zakeyah A A, Whitt J, Duke C, Gilmore D F, Meeker D G, Smeltzer M S and Alam M A 2018 Synthesis and antimicrobial studies of hydrazone derivatives of 4-[3-(2,4-difluorophenyl)-4-formyl-1H-pyrazol-1-yl]benzoic acid and 4-[3-(3,4-difluorophenyl)-4-formyl-1 H-pyrazol-1-yl]benzoic acid Bioorg. Med. Chem. Lett. 28 2914
Le T D, Pham N N and Nguyen T C 2018 Preparation and antibacterial activity of some new 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives J. Chem. 2018 Article ID 4301847.
Yurttaş L, Özkay Y, Kaplancıklı Z A, Tunalı Y and Karaca H 2013 Synthesis and antimicrobial activity of some new hydrazone-bridged thiazolepyrrole derivatives J. Enzyme Inhib. Med. Chem. 28 830
Kumar N and Chauhan L S 2015 Antimicrobial potential of hydrazide-hydrazone derivatives: a review Int. J. Pharm. Clin. Res. 7 154
Angelova V, Karabeliov V, Andreeva-Gateva P A and Tchekalarova J 2016 Recent developments of hydrazide/hydrazone derivatives and their analogs as anticonvulsant agents in animal models Drug Dev. Res. 77 379
Kumar N, Chauhan L S, Dashora N and Sharma C S 2014 Anticonvulsant potential of hydrazone derivatives: A review Sch. Acad. J. Pharm. 3 366
Agrawal S, Jain J, Kumar A, Gupta P and Garg V 2020 Synthesis molecular modeling and anticonvulsant activity of some hydrazone, semicarbazone, and thiosemicarbazone derivatives of benzylidene camphor Res. Rep. Med. Chem. 49 237
Verma G, Marella A, Shaquiquzzaman M, Akhtar M, Ali M R and Alam M M 2014 A review exploring biological activities of hydrazones J. Pharm. Bioallied Sci. 6 69–80
The authors thank Dr. Dilip Thube, PG Department of Chemistry, New Arts, Commerce and Science College Parner, University of Pune; Mr. Sridhar Yerpal, Bhavesh Chemical, Hyderabad; and Mrs. Ashvini Shingade, Mumbai for their valuable guidance and providing necessary facilities.
About this article
Cite this article
Gagare, D., Patil, R., Lokhande, R. et al. Synthesis and characterization of (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol from 2-hydroxy-4,5-dimethylacetophenone. J Chem Sci 132, 88 (2020). https://doi.org/10.1007/s12039-020-01802-4