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过去十年(2014年至2024年)间1,4 - 苯并噻嗪合成方法的进展。

Evolution in the synthesis of 1,4-benzothiazines over the last decade (2014 to 2024).

作者信息

Rundla Hemant Kumar, Soni Shivani, Teli Sunita, Agarwal Shikha, Agarwal Lokesh Kumar

机构信息

Department of Chemistry, Mohanlal Sukhadia University Udaipur Rajasthan 313001 India

出版信息

RSC Adv. 2025 Feb 24;15(8):6122-6146. doi: 10.1039/d4ra08949a. eCollection 2025 Feb 19.

DOI:10.1039/d4ra08949a
PMID:39995460
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11849341/
Abstract

1,4-Benzothiazine (1,4-BT) is a heterocyclic compound consisting of a benzene ring fused with a thiazine ring, incorporating both nitrogen and sulfur atoms. The fusion of the benzene and thiazine frameworks enhances its biological properties, making it a valuable scaffold for designing innovative heterocyclic systems. This versatile and significant member of the heteroarene family bridges synthetic organic chemistry with medicinal, pharmaceutical, and industrial applications. This structural motif demonstrates remarkable potential for accommodating a wide range of substrates and functionalizations, giving rise to diverse biological activities such as antipsychotropic, antiviral, antithyroid, antimicrobial, antifungal, antitubercular, antioxidant, and anti-inflammatory properties. Numerous derivatives have been synthesized as target structures in drug development. This review highlights various synthetic approaches to prepare 1,4-BTs. Well-established methods, such as the reactions of 2-aminothiophenol (2-ATP) with alkenes, enaminones, carboxylic acids, esters, furan-2,3-dione, aroylmethylidene malonate and 1,3-dicarbonyl compounds, are summarized. Additionally, the miscellaneous syntheses of 1,4-BTs were also outlined. These methods have utilized various catalysts, including nanocatalysts and metal-based catalysts, under diverse reaction conditions for efficient synthesis. The deep analysis of the synthesis of 1,4-BTs will grasp the scientific community towards their synthetic aspects and further advances in the field.

摘要

1,4-苯并噻嗪(1,4-BT)是一种杂环化合物,由一个与噻嗪环稠合的苯环组成,含有氮和硫原子。苯环和噻嗪骨架的稠合增强了其生物学性质,使其成为设计创新杂环体系的有价值骨架。杂芳烃家族中这种多功能且重要的成员将合成有机化学与医学、制药和工业应用联系起来。这种结构基序显示出容纳广泛底物和官能化的显著潜力,产生了多种生物活性,如抗精神失常、抗病毒、抗甲状腺、抗菌、抗真菌、抗结核、抗氧化和抗炎特性。许多衍生物已被合成为药物开发中的目标结构。本综述重点介绍了制备1,4-苯并噻嗪的各种合成方法。总结了一些成熟的方法,如2-氨基硫酚(2-ATP)与烯烃、烯胺酮、羧酸、酯、呋喃-2,3-二酮、芳酰基亚甲基丙二酸酯和1,3-二羰基化合物的反应。此外,还概述了1,4-苯并噻嗪的其他合成方法。这些方法在不同的反应条件下使用了各种催化剂,包括纳米催化剂和金属基催化剂,以实现高效合成。对1,4-苯并噻嗪合成的深入分析将使科学界了解其合成方面以及该领域的进一步进展。

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