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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 | Revised: 03 Sep 2011 | Accepted: 23 Sep 2011 | Published: 31 Mar 2012 | Issue Date: March 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.
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DOI: 10.5155/eurjchem.3.1.106-111.489
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Funding information
University Grants Commission (Research Award Scheme) and Council of Scientific and Industrial Research, New Delhi
Citations
[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
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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
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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
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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
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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
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RSC Advances 6(1), 201, 2016
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[7]. Shafia Mir, Ayaz Mahmood Dar, Bashir Ahmad Dar
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Mini-Reviews in Organic Chemistry 17(2), 148, 2020
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[8]. 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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[9]. 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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DOI Link: https://doi.org/10.5155/eurjchem.3.1.106-111.489
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European Journal of Chemistry 2012, 3(1), 106-111 | doi: https://doi.org/10.5155/eurjchem.3.1.106-111.489 | Get rights and content
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