European Journal of Chemistry 2012, 3(1), 106-111. doi:10.5155/eurjchem.3.1.106-111.489
OPEN ACCESS

Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides


Naveen Gautam (1) , Neha Ajmera (2,*) , Shikha Gupta (3) , Dinesh Chand Gautam (4)

(1) Department of Chemistry, University of Rajasthan, Jaipur-302004, India
(2) Department of Chemistry, University of Rajasthan, Jaipur-302004, India
(3) Department of Chemistry, University of Rajasthan, Jaipur-302004, India
(4) Department of Chemistry, University of Rajasthan, Jaipur-302004, India
(*) Corresponding Author

Received: 16 Jul 2011, Accepted: 23 Sep 2011, Published: 31 Mar 2012

Abstract


Synthesis of heterocyclic compounds like benzothiazines has attracted attention in recent years due to their biological and industrial value. This article reflects up-to-date and comprehensive coverage of biochemical aspects of benzothiazines, their sulfones and ribofuranosides. The nitrogen and sulfur containing heterocycles were prepared by condensation followed by oxidative cyclization of 2-aminobenzenethiol with β-diketones/β-ketoesters in dimethylsulfoxide. These compounds were then used as base to prepare ribofuranosides by treating them with sugar (β-D-ribofuranose-1-acetate-2,3,5-tribenzoate). On refluxing with hydrogen peroxide in glacial acetic acid, these substituted dimethyl 4H-1,4-benzothiazines yielded 4H-1,4-benzothiazine-1,1-dioxides. Antioxidant and antimicrobial activity of these compounds were carried out and structure evaluation was done by spectral and elemental analysis.

3_1_106_111_800


Keywords


Sulfones; Heterocycles; Ribofuranosides; Antioxidant activity; Antimicrobial activity; 4H-1,4-benzothiazines

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DOI: 10.5155/eurjchem.3.1.106-111.489

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Citations

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[1]. Ya-mei Lin, Guo-ping Lu, Rong-kang Wang, Wen-bin Yi
Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions
Organic Letters  18(24), 6424, 2016
DOI: 10.1021/acs.orglett.6b03324
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[2]. Somarathinam Kanagasabai, Kothandan Gugan, Mandapati Bhargav Reddy, Ramasamy Anandhan, S. Madan Kumar, S. Usharani
Crystal structure and hirshfeld surface analysis of 2,2′-Bi-(3-phenyl-2H-1,4-benzothiazine)
Chemical Data Collections  20, 100189, 2019
DOI: 10.1016/j.cdc.2019.100189
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[3]. Veronika Fülöpová, Anna Krchňáková, Eva Schütznerová, Jaroslav Zajíček, Viktor Krchňák
Ring Contraction of 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-Dioxides: Access to 4H-Benzo[b][1,4]thiazine 1,1-Dioxides
The Journal of Organic Chemistry  80(3), 1795, 2015
DOI: 10.1021/jo502713k
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[4]. Nada Kheira Sebbar, Mohamed Ellouz, Younes Ouzidan, Manpreet Kaur, El Mokhtar Essassi, Jerry P. Jasinski
(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine
IUCrData  2(6), , 2017
DOI: 10.1107/S2414314617008902
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[5]. Brahim Hni, Nada Kheira Sebbar, Tuncer Hökelek, Younes Ouzidan, Ahmed Moussaif, Joel T. Mague, El Mokhtar Essassi
Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzothiazin-3-one
Acta Crystallographica Section E Crystallographic Communications  75(3), 372, 2019
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[6]. Shubhanjan Mitra, Sayani Mukherjee, Alakananda Hajra
Peroxide-free synthesis of benzo[b][1,4]thiazine 1,1-dioxides and their antimicrobial study
RSC Advances  6(1), 201, 2016
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[7]. Ahmed A. El-Barbary, Ashraf A. El-Shehawy, Nabiha I. Abdo
Synthesis and Antimicrobial Activities of Some 6-Methyl-3-Thioxo-2,3-Dihydro-1,2,4-Triazine Derivatives
Phosphorus, Sulfur, and Silicon and the Related Elements  189(3), 400, 2014
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[8]. Naveen Gautam, Ankita Garg, Dinesh Chand Gautam
Synthesis, Spectral Characterization, and Pharmacological Importance of New 4H-1,4-Benzothiazines, Their Sulfone Analogues, and Ribofuranosides
Nucleosides, Nucleotides and Nucleic Acids  34(1), 40, 2015
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How to cite


Gautam, N.; Ajmera, N.; Gupta, S.; Gautam, D. Eur. J. Chem. 2012, 3(1), 106-111. doi:10.5155/eurjchem.3.1.106-111.489
Gautam, N.; Ajmera, N.; Gupta, S.; Gautam, D. Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides. Eur. J. Chem. 2012, 3(1), 106-111. doi:10.5155/eurjchem.3.1.106-111.489
Gautam, N., Ajmera, N., Gupta, S., & Gautam, D. (2012). Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides. European Journal of Chemistry, 3(1), 106-111. doi:10.5155/eurjchem.3.1.106-111.489
Gautam, Naveen, Neha Ajmera, Shikha Gupta, & Dinesh Chand Gautam. "Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides." European Journal of Chemistry [Online], 3.1 (2012): 106-111. Web. 7 Dec. 2019
Gautam, Naveen, Ajmera, Neha, Gupta, Shikha, AND Gautam, Dinesh. "Synthesis, spectral characterization and biological evaluation of 4H-1,4-benzothiazines, their sulfones and ribofuranosides" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

DOI Link: https://doi.org/10.5155/eurjchem.3.1.106-111.489

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