Characterization of the Structure of 2-(4-methyl-2 Phenyl-4, 5-dihydrooxazol-4-ylmethyl)-isoindole-1, 3-dione by 1D, COSY and HSQC 2D NMR Spectroscopy
Asian Journal of Chemical Sciences,
Page 30-37
DOI:
10.9734/ajocs/2021/v9i319074
Abstract
The identity of the 2-(4-Methyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl)-isoindole-1,3-dione, previously synthesized in our laboratory, was proven without doubt by means of 1D and 2D NMR spectroscopy. Two-dimensional NMR spectroscopy played a major role. The analysis of the 2D-COSY spectrum of isoindoline-1,3-dione derivative shows a perfect correlation between neighboring protons. Thus, a correlation was noted between the protons of the phthalimide, H(8) and H(9) on the one hand and H(8') and H(9') on the other hand. The analysis of the 2D-HSQC spectrum of the studied compound indicates a faultless correlation between protons and adjacent carbons, and no correlation in the case of all quaternary carbons.
Keywords:
- Isoindoline
- 1,3-dione
- 1D NMR
- 2D COSY
- 2D HSQC
How to Cite
Dioukhane, K., Aouine, Y., Nakkabi, A., Boukhssas, S., Faraj, H., & Alami, A. (2021). Characterization of the Structure of 2-(4-methyl-2 Phenyl-4, 5-dihydrooxazol-4-ylmethyl)-isoindole-1, 3-dione by 1D, COSY and HSQC 2D NMR Spectroscopy. Asian Journal of Chemical Sciences, 9(3), 30-37. https://doi.org/10.9734/ajocs/2021/v9i319074
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Hamou N, Ibrahimi S, Salem M, Mokhtar E, Amzazi S, Benjouad A. Synthèse et propriétés biologiques benzodiazepines. 2001;4:917-924. DOI: 10.1016/S1387-1609(01)01302-0.
Zniber. Heterocycles from benzimidazole. Tetrahedon Leters. 1990;31:5467. DOI: 10.1016/S0040-4039(00)97874-2.
Kim D et al. Antagonists : Effects of fused heterocycles on antiviral activity and pharmacokinetic properties. 2005;15:2129-2134. DOI: 10.1016/j.bmcl.2005.02.030.
Maaliki C et al. Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM. Bioorganic Med. Chem. 2020;28 (13):115579. DOI: 10.1016/j.bmc.2020.115579.
Kumar S, Verma R, Verma S, Vaishnav Y. European journal of medicinal chemistry anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives : A key review. Eur. J. Med. Chem. 2021;209:112886. DOI: 10.1016/j.ejmech.2020.112886.
Murthy PK et al. Towards the new heterocycle based molecule: Synthesis, characterization and reactivity study. J. Mol. Struct. 2017;1137:589–605. DOI: 10.1016/j.molstruc.2017.02.071.
Chakraborty B, Chettri E. Results in chemistry mechanochemical synthesis of some heterocyclic molecules using Sonogashira cross-coupling reaction and their anticancer activities. Results Chem. 2020;2:100037. DOI: 10.1016/j.rechem.2020.100037.
Aouad MR, Almehmadi MA, Rezki N, Al Blewi FF, Messali M, Ali I. Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles. J. Mol. Struct. 2019;1188;153-164. DOI: 10.1016/j.molstruc.2019.04.005.
Maaliki C et al. Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM. Bioorganic Med. Chem. 2020;28 (13):15579 DOI: 10.1016/j.bmc.2020.115579.
Kumar S, Verma R, Verma S, Vaishnav Y. European journal of medicinal chemistry anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives : A key review. Eur. J. Med. Chem. 2021;209:112886. DOI: 10.1016/j.ejmech.2020.112886.
Patel TS, Bhatt JD, Dixit RB, Chudasama CJ, Patel BD, Dixit BC. Green synthesis, biological evaluation, molecular docking studies and 3D-QSAR analysis of novel phenylalanine linked quinazoline-4(3H)-one-sulphonamide hybrid entities distorting the malarial reductase activity in folate pathway. Bioorganic Med. Chem. 2019; 27(16):3574–3586 DOI: 10.1016/j.bmc.2019.06.038.
Andrejević TP et al. Zinc(II) complexes with aromatic nitrogen-containing heterocycles as antifungal agents: Synergistic activity with clinically used drug nystatin. J. Inorg. Biochem., 2020;208: 111089
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Song YQ. A 2D NMR method to characterize granular structure of dairy products. Prog. Nucl. Magn. Reson. Spectrosc. 2009;55(4):324–334. DOI: 10.1016/j.pnmrs.2009.07.001.
Jiang L, Howlett K, Patterson K, Wang B. Introduction of a new method for two-dimensional NMR quantitative analysis in metabolomics studies. Anal. Biochem. 2020;597:113692 DOI: 10.1016/j.ab.2020.113692.
Snyder DA. Covariance NMR: Theoretical concerns, practical considerations, contemporary applications and related techniques. Prog. Nucl. Magn. Reson. Spectrosc. 2021;122:1-10 DOI: 10.1016/j.pnmrs.2020.09.001.
Michal CA. Low-cost low-field NMR and MRI: Instrumentation and applications. J. Magn. Reson. 2020;319:106800. DOI: 10.1016/j.jmr.2020.106800.
Kaiser CR. 2D NMR: Inverse detection and field gradient in structure determination of organic compounds. Quim. Nova. 2000;23 (2):231–236. DOI: 10.1590/S0100-40422000000200014. Riegel SD, Leskowitz GM. TrAC, 2016;8327-38.
Dioukhane K et al. Synthesis, crystal structure and IR spectrum studies of 2-(4-methyl-2-phenyl-4,5-dihydro-oxazol-4-ylmethyl)- isoindole-1,3-dione. Mediterr. J. Chem. 2019;9(2):116-124.
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