Synthesis Identification of the New Heterocyclic System from Lactam
Main Article Content
Abstract
The importance of heterocyclic compounds has long been recognized, and the use of chemicals has remained constant, including in the manufacturing of pharmaceuticals. Several lactam synthesis methods have been developed. Among the essential compounds in our lives are lactams from amines and aldehydes and the preparation of Schiff bases. Schiff bases are prepared in two ways, including the reaction of hydrazine and various aldehydes with tetraethylamine and the production of a Schiff base, which leads to the formation of two types of lactams and the preparation of a kind of reaction of different amines and aldehydes. Three techniques prepared the lactams, the first being Schiff bases with acetyl chloride and triethylamine as catalysts and using dioxane as the solvent; The second is from Schiff bases with carboxylic acids; The third is aldehydes with amines. It produces beta-lactam derivatives (azetidine), and this research focuses on the production of lactams and their polymerization through their reaction with ethanol once and with ethanol and the base to form industrial polymers, which are polymers that are produced in the form of a final product with an active end and are used in many industries. These polymers have moderate to high antioxidant activity, and after being treated with safer natural materials, they are environmentally friendly compared to other materials. Its chemical composition was evaluated by the following required tests (FTIR, HNMR).
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
licenseTerms
Publication Dates
Received
Accepted
Published Online First
References
Ombito, J.O.; Singh, G.S. Recent Progress in Chemistry of β-lactams. Mini Reviews in Organic Chemistry. 2019, 16(6), 544-567. http://dx.doi.org/10.2174/1570193X15666180914165303.
Qiu, M.; Fu, X.; Fu, P. Huang , J. Construction Of Aziridine, Azetidine, Indole and Quinoline-Like Heterocycles: Via Pd-Mediated C-H Activation/Annulation Strategies. Organic and Biomolecular Chemistry. 2022, 20(7), 1339–1359. .https://doi.org/10.1039/d1ob02146j.
Khan, S.A.; Zain, Z.M.; Mansoor, M.; Mahfuz, M.M.H.; Rahman, A.; Rashid, M.A.N.; Rais, M.S. Performance Investigation of Zno/PVA Nanocomposite Film for Organic Solar Cell. Materials Today: Proceedings. 2021, 47(11), 2615-2621. https://doi.org/10.1016/j.matpr.2021.05.197.
Linder, M.R.; Podlech, J. Synthesis Of Β-Lactams From Diazoketones And Imines:The Useofmicrowaveirradiation. OrganicLetters. 2001, 12, 18491851. https://doi.org/10.1021/ol015891.
Riemer, N.; Riemer, M.; Krüger, M.; Clarkson, G.; Shipman, M.; Schmidt, B. Synthesis of Arylidene-β-Lactams Via Exo-Selective Matsuda-Heck Arylation of Methylene-Β-Lactams. Journal of Organic Chemistry. 2021, 86(13), 8786–8796. https://doi.org/10.1021/acs.joc.1c00638.
Shweish, B.K.; Narran, S.F. Preparation, Characterazation, Study Biological Activities with Some Newchalcone Derivatives. NVEO-NATURAL VOLATILES & ESSENTIAL OILS Journal| NVEO. 2021, 8(4), 3765-3782. https://doi.org/index.php/journal/article/view/970
Muslim, R.F.; Tawfeeq, H.M.M.O. ACTA Pharmaceutica Synthesis, Characterization and Evaluation of Antifungal Activity of Seven-Membered Heterocycles. Journal of Saudi Chemical Society. 2018, 15(10.23893), 1307–2080. https://doi.org/10.23893/1307-2080.aps.05610.
Al-Mashhadan, H.A.A.; Al-Dahhan, M.W.; Hashim, H.; Yousif, E. Synthesized and Designed New Modified Poly (vinylchloride) Structures to Enhance their Photo Resistance Characteristics. Chemistry. 2022, 4(4), 1101-1122. https://doi.org/10.3390/chemistry4040075.
Henary, M.; Kada, C.; Rotolo, L.; Savino, B.; Owens, A.; Cravotto, G. Benefits and Applications of Microwave-Assisted Synthesis of Nitrogen Containing Heterocycles in Medicinal Chemistry. RSC Advances. 2020, 10(24), 14170–14197. https://doi.org/10.1039/d0ra01378a.
Radhiyah, K.; Ezet, H. Synthesis and Characterization of Some New β-Lactam Derivatives from Azosulphadiazine and their Biological Evaluation as Anticancer. Orient J Chem. 2018, 34(1), 371–380. https://doi.org/10.13005/ojc/340140.
Cebeci, Y.U.; Bayrak, H.; Şirin, Y. Synthesis Of Novel Schiff Bases and Azol-Β-Lactam Derivatives Starting from Morpholine and Thiomorpholine and Investigation of their Antitubercular, Antiurease Activity, Acethylcolinesterase Inhibition Effect and Antioxidant Capacity. Bioorganic Chemistry. 2019, 88, 102928. https://doi.org/10.1016/j.bioorg.2019.102928.
Mezaal, W.N.N.; ALsahib, S.A. Synthesis Characterization of New Derivatives using Schiff’s Bases for Alcoholic Extract of (Cordia Myxa) Medical Plant. Eurasian Chemical Communications. 2022, 4(11), 1054–1061. https://doiorg/10.22034/ecc.2022.343900.1473.
Zarei, M.; Jarrahpour, A. A Mild Efficient Route to 2-Azetidinones Using The Cyanuric Chloride-DMF Complex. Synlett. 2011, 22(17), 2572–2576. http://dx.doi.org/10.1055/s-0030-1289517.
Henary, M.; Kananda, C.; Rotolo, L.; Savino, B.; Owens, EA.; Cravotto, G. Benefits and Applications of Microwave-Assisted Synthesis of Nitrogen Containing Heterocycles in Medicinal Chemistry. RSC Advances. 2020, 10(24), 14170-14197. https://doi.org/10.1039/d0ra01378a.
Synofzik, J. α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. Journal of Organic Chemistry. 2019, 84(18), 12101–12110. https://doi.org/10.1021/acs.joc.9b02030.
Verdino, A. Synthesis and Biological Evaluation of the Progenitor of a New Class of Cephalosporin Analogues, with a Particular Focus on Structure-Based Computational Analysis. PLOS ONE. 2017, 12(7), e0181563. https://doi.org/10.1371/journal.pone.0181563.
Thejeel, K.A .; Ascar, I.; Hussein, M. Synthesis of New Polymers Linked to Heterocyclic using Zinc Oxide with Nanostructures Extracted from Natural Sources. Egyptian Journal of Chemistry. 2022, 65(4), 579–589. https://doi.org/10.21608/EJCHEM.2021.92971.4644.
Elamri, A., A.; Zdiri, K.; Harzallah, O. Chitosan: A Biopolymer for Textile Processes and Products. Textile Research Journal. 2023, 93(56), 1456-1484. https://doi.org/10.1177/00405175221127315.
Kumar, A. Synthesis of Some New Schiff Bases of Pharmaceutical Interest. Annals of Advances in Chemistry. 2017, 1(2), 053–056. https://doi.org/10.29328/journal.aac.1001006.
Azeez, H.N., Al-kadhimi, A.A.H.; Tapabashi, N.O. Synthesis, Characterization and Biological Evaluation of Some Azo and Azo-Schiff Compounds. Kirkuk Journal of Scientific Researches. 2019, 14(1), 97–119. https://doi.org/10.32894/kujss.2019.14.1.8.
Grabrijan, K.; Stanislav, G. Synthesis of 3-Amino-4-substituted Monocyclic ß-Lactams Important Structural ORCID. Synthesis of 3-Amino-4-substituted Monocyclic ß-Lactams—Important Structural Motifs in Medicinal Chemistry. International Journal of Molecular Sciences. 2022, 23(1), 360. https://doi.org/10.3390/ijms23010360.
Faltracco, M.; Sukowski, V.; van Druenen, M.; Hamlin, T.A.; Bickelhaupt, F.M.; Ruijter, E. Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation. Journal of Organic Chemistry. 2020, 85(15), 9566–9584.
https://doi.org/10.1021/acs.joc.0c00575.
Beatriz, A.; Mondino, M.G.; de Lima, D. P. Lactams, Azetidines, Penicillins, and Cephalosporins: An Overview on the Synthesis and Their Antibacterial Activity. N-Heterocycles: Synthesis and Biological Evaluation. 2022, 97–142. http://dx.doi.org/10.1007/978-981-19-0832-3_3.
Blizzard, T.A.; Chen, H.; Kim, S.; Wu, J.; Bodner, R.; Gude, C. Imbriglio, J.; Young, K.; Park, Y-W.; Ogawa, A.; Raghoobar, S.; Hairston, N.; Painter, R.E.; Wisniewski, D.; Scapin, G.; Fitzgerald, P.; Sharma, N.; Lu, J.; Ha, Sh.; Hermes, J.; Hammond, M.L. Discovery of MK-7655, A β- Lactamase Inhibitor for Combination with Primaxin®. Bioorganic & Medicinal Chemistry Letters. 2014, 24(3), 780–785. https://doi.org/10.1016/j.bmcl.2013.12.101.
Nagel, K.; Spange, S. Polyamide/Silica Hybrid Materials by Anionic Melt Polymerization of Lactam-Substituted Silane Monomers with Ε-Caprolactam. European Polymer Journal. 2019, 113, 385–394. https://doi.org/10.1016/j.eurpolymj.2019.01.072.
Cheibas, C.; Cordier, M.; Li, Y.; El Kaïm, L. A Ugi Straightforward Access to Bis-βlactam Derivatives. European Journal of Organic Chemistry. 2019, 27, 4457–4463. https://doi.org/10.1002/ejoc.201900678.
Devalina S, A. K. Conducting Polymer-Based Ternary Composites for Super capacitor Applications. Egyptian Journal of Chemistry. 2019, 10(2), 301–332. https://doi.org/10.1002/ejoc.201900678.
Faltracco, M.; Sukowski, V.; van Druenen, M.; Hamlin, T.A.; Bickelhaupt, F.M.; Ruijter, E. Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation. Journal of Organic Chemistry. 2020, 85(15), 9566–9584. https://doi.org/10.1021/acs.joc.0c00575.
Gan, Y.; Ma, S.; Guo, X.; Chen, B.; Jassby, D. Photolysis Of Chloral Hydrate In Water With 254 Nm Ultraviolet: Kinetics, Influencing Factors, Mechanisms, and Products. Chemosphere. 2019, 218(2), 104–109. https://doi.org/10.1016/j.chemosphere.2018.11.065.
Gaume, J.; Wong-Wah-Chung, P.; Rivaton, A.; Thérias, S.; Gardette, J-L. Photochemical Behavior Of PVA as an Oxygen-Barrier Polymer for Solar Cell Encapsulation. RSC Advances. 2011, 1(8), 1471–1481. http://dx.doi.org/10.1039/C1RA00350J.
Hasan, N.A.; Baqer, Sh.R. Preparation, Characterization, Theoretical and Biological Study of new Complexes with mannich base , 2chloro –N-5-(Piperidin -1-ylmethylthio)-1, 3, 4- Thiadiazol-2-yl)acetamide. Ibn AL-Haitham Journal For Pure and Applied Sciences. 2023, 36(1), 260-271. https://jih.uobaghdad.edu.iq/index.php/j/article/view/2983.