Abstract :
: In this study we report the synthesis of a series of 2-Azetidinones from N-(4-(5-bromothiophen-2-yl)-6-(4-chlorophenyl)pyrimidin-2- yl)-1-(aryl) methanimine. A mixture of N-(4-(5-bromothiophen-2-yl)-6-(4-chlorophenyl)pyrimidin-2- yl)-1-(aryl) methanimine and triethyl amine was reacted with chloroacetyl chloride in 1,4-dioxane. The N-(4-(5-bromothiophen-2-yl)-6-(4 -chlorophenyl) pyrimidin-2- yl)-1-(aryl) methanimine was prepared from reaction of 4-(5-bromothiophene-2-yl)-6-(4-chloropheneyl)pyrimidin-2-amine with aromatic aldehydes in ethanol in presence of catalytic acetic acid. All newly synthesized compounds were characterized on the basis of 1H NMR, IR, and MASS spectral data.
Keywords :
2-Azetidinones, Schiff bases Pyrimidine, Spectral CharacterizationReferences :
- Monier M., El-Mekabaty A., Elattar K.M. Five-membered ring systems with one heteroatom: synthetic routes, chemical reactivity, and biological proper- ties of furan-carboxamide analogues, Synth. Commun. 48 (8), 2018, pp.839–875.
- Mert B.D., Elattar K.M. Seven-membered rings with three heteroatoms: chemistry of 1, 2, 5-and 1, 4, 5-thiadiazepines, Curr. Org. Chem. 22 (4), 2018, pp. 386–410
- Zarenezhed E., Farjam M., and Iraji A. Synthesis and biological activity of pyrimidine-containing hybrids: Focusing on pharmacological application. Journal of Molecular Structure.1230, 2021, pp.129833
- Cwikla A. S., Regeic A., Zimecki M., Artym J., Zaczynska E., Kocieba M., Bryndal M., Pyra A. and Maczynski M. Synthesis and biological activity of new 7-amino-oxazolo[5,4-d] pyrimidine derivatives. Molecules, 25, 2020, 3558; doi:10.3390/molecules25153558
- Abdellattif M. H., Shahbaaz M., Arief M. M. H. and Hussien M. A. Oxazinethione Derivatives as a Precursor to pyrazolone and pyrimidine derivatives: Synthesis, biological activities, molecular modelling, ADME and molecular dynamics studies. Molecules. 26, 2021, 5482. https://doi.org/10.3390/molecules26185482
- Triloknadh S., Venkata Rao C., Nagarju K., Krishna N. H., Ramaiah C. V., Rajendra W., Trinath D., Suneetha Y. Design, synthesis, neuroprotective, antibacterial activities and docking studies of novel thieno[2,3-d]pyrimidine-alkyne Mannich base and oxadiazole hybrids. Bioorganic and Medicinal Chemistry letters. 28 (9), 2018, pp. 1663-1669
- Ding R., Wang X., Jainfang Fu. Chang Y., Yingxue Li., Yajing Liu., Yue Liu, Jinlong Ma Jinxing Hu. Design, synthesis and antimicrobial activity of novel pleuromutilin derivatives with thieno[2,3-d]pyrimidine substitution. European Journal of Medicinal Chemistry. 237, 2022, 114398, https://doi.org/10.1016/j.ejmech.2022.114398
- Luzhnova S. A., Tyrkov A. G., Gabitova N. M. and Yurteava E. A. Synthesis and antimicrobial activity of 5-(arylmethylidine)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones. Pharmaceutical Chemistry journal. 52, 2018, pp.506-509
- Bai S., Liu S., Zhu Y., Qin Wu. Asymmetric synthesis and antiviral activity of novel chiral amino-pyrimidine derivatives. Tetrahedron Letters. 59 (33), 2018, pp. 3179-3183.
- Krecmerova M., Dracinsky M., Snoeck R., Balzarini J. Pomeisl K. and Andrei G. New prodrugs of two pyrimidine acyclic nucleoside phosphonates: Synthesis and antiviral activity. Bioorganic and Medicinal Chemistry. 25 (17), 2017, pp. 4637-4648
- W., Lan W., Wu C. and Fei Q. Synthesis and antifungal activity of pyrimidine derivatives containing an amide moiety. Front. Chem. 9, 2021, https://doi.org/10.3389/fchem.2021.695628
- Parmar K., Patel R., Prajapati S., Joshi S. and Patel R. Synthesis and antimicrobial activity of novel 3-chloro-[1-(3,6-(diphenyl)[1,2,4] triazolo [3,4b] [1,3,4] thiadiazole]-4-(3,4-diethoxy phenyl)-azetidin-2-one and their derivatives. Journal of Applied Pharmaceutical Science. 2(1), 2012, pp. 114-118
- Patel N. B. and Patel M. D. Synthesis and evaluation of antibacterial and antifungal activities of 4-thiazolidinones and 2-azetidinones derivatives from chalcone. Medicinal Chemistry Research. 26, 2017, pp. 1772-1783.
- Zangade S., Shinde S., Nalwar Y. and Patil P. Microwave assisted synthesis and antimicrobial study of some novel 2-azetidinones derived from 2-(1-phenylimino-ethyl)-naphthalein-1-ol. Orbital. 11 (3), 2019,
http://dx.doi.org/10.17807/orbital.v11i3.1393
- Kayarmar R., Nagaraja G. K., Naik P., Manjunatha H., Revanasiddappa B. C. and Arulmoli T. Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents. Journal of Saudi Chemical Society. 21 (1), 2017, S434- S444.
- Govindarao K., Shrinivasan N., Raheja R. K., Annadurai S., Bhandare R. R. and Shaik A. B. Quinoline conjugated 2-azetidinone derivative as prospective anti-breast cancer agent: In vitro antiproliferative and anti-EGFR activities, molecular docking and in-silico drug likeliness studies. Journal of Saudi Chemical Society. 26 (3), 2022, pp. 101471
- Rashidi M., Islami M. R. and Mahani S. E. Design and stereoselective synthesis of novel β-lactone and β-lactam as potent anticancer agents on breast cancer cells. Tetrahedron. 74 (8), 2018, pp. 835-841.
- Archana Saini S. Synthesis and anticonvulsant studies of thiazolidinones and azetidinone derivatives from indole moiety. Drg Res. 69 (8), 2019, pp. 445-450
- Al- Khazragie Z. B., Al-Salami B. K. and Al-Fartosy A. J. M. Synthesis, antimicrobial, antioxidant and anticancer activity of a new azetidinone, thiazolidinone and selenazolidinone derivative based on sulfonamide. Indones. J. Chem. 22 (4), 2022, pp. 979-1001
- Thomas A. B., nanda R. K., Kothapalli L. P. and hamane S. C. Synthesis and biological evaluation of Schiff bases and 2-azetidinones of isonocotinyl hydrazone as potential antidepressant and nootropic agents. 9 (1), 2016, pp. S79-S90.
- Manohare S. V. and Thakare S. S. Synthesis and antimicrobial evaluation of pyrimidines derived from chalcones. Res. J. Chem. Environ. 23, 2019, pp. 84-88.