Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2017-09-28 DOI:10.1021/acs.oprd.7b00260

Shixian Deng, Zhenzhuang Cheng, Charles Ingalls, Ferenc Kontes, Jiaming Yan, Sandro Belvedere*

引用次数: 2

Abstract

We report an efficient and scalable synthesis of 7-methoxy-2,3,4,5-tetrahydrobenzo[1,4]thiazepine, the core structure of biologically active molecules like JTV-519 and S107. This synthetic route, starting with 4-methoxythiophenol and proceeding via acyliminum cyclization, gives the target product in four steps and 68% overall yield and is a substantial improvement over previously published processes. Nine additional examples of tetrahydrobenzo[1,4]thiazepine synthesis via acyliminium ring closure are also presented.

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n -酰基环化法合成2,3,4,5-四氢苯并[1,4]噻唑类药物

我们报道了一种高效、可扩展的7-甲氧基-2,3,4,5-四氢苯并[1,4]噻吩的合成，这是生物活性分子如JTV-519和S107的核心结构。该合成路线从4-甲氧基噻吩开始，经过乙酰氨基环化，在四个步骤中得到目标产品，总收率为68%，与先前发表的工艺相比有了实质性的改进。通过酰基铝环闭合法合成四氢苯并[1,4]噻嗪类化合物的另外九个例子也被提出。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.