Synthesis of New Hydrazones Containing 1,3-Diketo Moiety
A series of novel hydrazones containing a 1,3-diketo moiety, namely 3-[(2E)-2-(4-hydroxybenzylidene)hydrazino]-3-oxo-N-phenylpropanamides (6a-j), were synthesized as precursors for biologically important β-lactam and thiazolidinone derivatives. The synthesis involved the condensation of 3-methoxy-4-hydroxybenzaldehyde or 3-methoxy-4-acetyloxybenzaldehyde with various substituted malonanilic acid hydrazides. The hydrazides (4a-e) were prepared by refluxing aniline with diethyl malonate, followed by treatment with hydrazine hydrate. The structures of the synthesized compounds were confirmed by elemental analysis and spectroscopic techniques, including IR, and 1H NMR spectrometry. The purity of the compounds was ascertained by thin-layer chromatography. The synthesized hydrazones (6a-j) were obtained in good yields (62-83%) and were soluble in dimethylformamide. The present study provides a foundation for further exploration of these 1,3-diketo amino compounds as promising scaffolds for developing novel heterocyclic compounds with diverse biological activities.
-
1.
Al-Kahraman, Y. M. S. A., Yasinzai, M., & Singh, G. S. (2012). Evaluation of some classical hydrazones of ketones and 1,2-diketones as antileishmanial, antibacterial and antifungal agents. Archives of Pharmacal Research, 35(6), 1009–1013. https://doi.org/10.1007/s12272-012-0608-7
-
2.
Cihan-Üstündağ, G., Şatana, D., Özhan, G., & Çapan, G. (2015). Indole-based hydrazide-hydrazones and 4-thiazolidinones: Synthesis and evaluation as antitubercular and anticancer agents. Journal of Enzyme Inhibition and Medicinal Chemistry, 1–12. https://doi.org/10.3109/14756366.2015.1024673
-
3.
Fang, Z.-Y., Qi, L., Song, J.-Y., Ren, P.-X., Hou, C.-Y., Ji, S.-C., Wang, L.-J., & Li, W. (2020). Phi(oac)2‐promoted 1,2‐diaza‐cope rearrangement of β,γ‐unsaturated hydrazones with acetate/h2o: Access to diacyl/acyl n‐allylhydrazines. European Journal of Organic Chemistry, 2020(33), 5464–5468. https://doi.org/10.1002/ejoc.202000875
-
4.
Halve, A. K., Bhashkar, B., Sharma, V., Bhadauria, R., Kankoriya, A., Soni, A., & Tiwari, K. (2008). Synthesis and in vitro antimicrobial studies of some new 3-[phenyldiazenyl] benzaldehyde N -phenyl thiosemicarbazones. Journal of Enzyme Inhibition and Medicinal Chemistry, 23(1), 77–81. https://doi.org/10.1080/14756360701408614
-
5.
Halve, A. K., Gour, P., Dubey, R., Bhadauria, D., & Bhaskar, B. (2005). Synthesis and antimicrobial screening of 2′-hydroxy-5’- (phenylazo)-N- (1″, 3″-diketophenylamine)-3-chloroazetidin-2-ones. Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry, 44(10), 2163–2165. https://doi.org/10.1002/chin.200604098
-
6.
Kaur, R., Singh, R., Ahlawat, P., Kaushik, P., & Singh, K. (2020). Contemporary advances in therapeutic portfolio of 2-azetidinones. Chemical Biology Letters, 7(1), 13–26.
-
7.
Kaur, R., Singh, R., Kumar, A., Kaur, S., Priyadarshi, N., Singhal, N. K., & Singh, K. (2020). 1,2,3-triazole β-lactam conjugates as antimicrobial agents. Heliyon, 6(6), Article e04241. https://doi.org/10.1016/j.heliyon.2020.e04241
-
8.
Kaur, R., Tripathi, D., Singh, K., & Singh, R. (2018). Recent advances in β-lactam chemistry. Journal of Integrated Science and Technology, 6(2), 46–51.
-
9.
Li, B., Liú, D., Hu, Y., Chen, J., Zhang, Z., & Zhang, W. (2021). Nickel‐catalyzed asymmetric hydrogenation of hydrazones. European Journal of Organic Chemistry, 2021(23), 3421–3425. https://doi.org/10.1002/ejoc.202100642
-
10.
Micheletti, G., Boga, C., Forlani, L., Del Vecchio, E., Zanna, N., Mazzanti, A., & Monari, M. (2017). Hydroxy‐ and methoxybenzene derivatives with benzenediazonium salts – Chemical behavior and tautomeric problems. European Journal of Organic Chemistry, 2017(5), 964–974. https://doi.org/10.1002/ejoc.201601393
-
11.
Monge, D., Daza, S., Bernal, P., Fernández, R., & Lassaletta, J. M. (2013). Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde n-tert-butyl hydrazone to nitroalkenes. Organic and Biomolecular Chemistry, 11(2), 326–335. https://doi.org/10.1039/c2ob26963e
-
12.
Nasseri, M. A., Salimi, M., & Esmaeili, A. A. (2014). Cellulose sulfuric acid as a bio-supported and efficient solid acid catalyst for synthesis of pyrazoles in aqueous medium. RSC Adv, 4(105), 61193–61199. https://doi.org/10.1039/C4RA11440J
-
13.
Prieto, A., Melot, R., Bouyssi, D., & Monteiro, N. (2015). Palladium‐catalyzed c(sp2)-h alkylation of aldehyde‐derived hydrazones with functionalized difluoromethyl bromides. Angewandte Chemie, 55(5), 1885–1889. https://doi.org/10.1002/anie.201510334
-
14.
Rathore, B. S., & Ittyerah, P. I. (1960). Synthesis of some new acid hydrazides and hydrazones. Journal of the Indian Chemical Society, 37, 591–593. https://doi.org/10.5281/zenodo.6538489
-
15.
Reddy, A. L. V. K. (2017). Synthesis, characterization and anti-inflammatory activity of hydrazones bearing 5-nitro-furan moiety and 5-iodo-vanillin hybrid. World Journal of Pharmaceutical Research, 982–993. https://doi.org/10.20959/wjpr201711-9635
-
16.
Safaei, S., Mohammadpoor-Baltork, I., Khosropour, A., Moghadam, M., Tangestaninejad, S., Mirkhani, V., & Khavasi, H. (2013). [Bmim][InCl4]-Catalyzed Addition of Hydrazones to β-Diketones: An Efficient Regioselective Synthesis of Pyrazoles and Pyrazole-Fused Cyclohexanones. Synlett, 24(9), 1086–1090. https://doi.org/10.1055/s-0032-1316900
-
17.
Syed Ameen, S. T., Vilvanathan, A., Khader, S. Z. A., & Mahalingam, G. (2020). Microwave-assisted green synthesis of β-diketone hydrazone derivatives and evaluation of their antioxidant and antibacterial activities. Current Microwave Chemistry, 7(3), 222–229. https://doi.org/10.2174/2213335607999200917145217
-
18.
Wei, D., Ma, H., Zhou, X., Shi, C., Luo, X., & Huang, G. (2017). Cobalt and copper co–catalyzed three‐component reactions for the synthesis of 1,3,4‐trisubstituted pyrazoles. ChemistrySelect, 2(22), 6231–6234. https://doi.org/10.1002/slct.201700987
-
19.
Yang, X., Zhang, S., Zhang, L., Zhang, B., & Ren, T. (2020). Rhombic dodecahedral cu2o‐catalysed synthesis of novel alkenyl pyrazoles. European Journal of Inorganic Chemistry, 2020(7), 613–616. https://doi.org/10.1002/ejic.201900959
-
20.
Yu, K., Meng, W., Feng, X., & Du, H. (2023). Asymmetric hydrogenation of hydrazones with chiral boranes. Organic Letters, 25(20), 3607–3610. https://doi.org/10.1021/acs.orglett.3c00843
| Section | Articles |
|---|---|
| Pages | 1-6 |
Most read articles by the same author(s)
- Raman Singh, Vidushi Gupta, Kuldeep Singh, Synthetic Methodologies and Biological Importance of Phosphonylpyrazoles , RSYN Chemical Sciences: Vol. 1 No. 1 (2024)
Similar Articles
- Raman Singh, Vidushi Gupta, Kuldeep Singh, Synthetic Methodologies and Biological Importance of Phosphonylpyrazoles , RSYN Chemical Sciences: Vol. 1 No. 1 (2024)
- Manisha Singhal, Seema Jangid, Deepak Singh Rajawat, Metal Organic Frameworks as Versatile Materials for Energy Storage, Environmental Remediation, and Catalytic Applications , RSYN Chemical Sciences: Vol. 1 No. 1 (2024)
- Auwalu Abdullahi Shehu, Preeti Pandey, Reena Kushwaha, Advanced analytical techniques for the identification of plant derived bioactive compounds , RSYN Chemical Sciences: Vol. 2 No. 1 (2025)
- Bhawna Sharma, Bhavya, A Comprehensive Review of Xylazine: Synthesis, Spectral Characterization, and Detection , RSYN Chemical Sciences: Vol. 2 No. 1 (2025)
- Narendra Verma, Prinyanka Gupta, Applications of Nanocomposites in Removal of Dyes from Wastewater: A Critical Review , RSYN Chemical Sciences: Vol. 2 No. 1 (2025)
- Kuldeep Singh, Inaugural Editorial , RSYN Chemical Sciences: Vol. 1 No. 1 (2024)
- Shweta Bansal, Arpita Roshni Behera, Prachi Singhal, Impact of Bioplastics Towards Sustainable Environment , RSYN Chemical Sciences: Vol. 1 No. 1 (2024)
- Reena Kushwaha, Auwalu abdullahi shehu, Dr. Preeti Pandey, Polymeric Innovations Driving Sensitivity in Electrochemical Analysis , RSYN Chemical Sciences: Vol. 2 No. 1 (2025)
- Mahesh Kumar Bhimwal, DR. APARANA PAREEK, Assessment and Management of Heavy Metal Contamination in Water Resources: Sources, Impacts, and Mitigation Strategies , RSYN Chemical Sciences: Vol. 2 No. 2 (2025)
You may also start an advanced similarity search for this article.
