One-Step, Catalyst-Free Continuous-Flow Method for the Rapid and Safe Synthesis of 1-Substituted 1H-Tetrazoles

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2024-09-05 DOI:10.1021/acs.oprd.4c00239

Zsolt Fülöp, Péter Bana, Márton Temesvári, Júlia Barabás, Zoltán Kazsu, Zoltán Béni, István Greiner, János Éles

引用次数: 0

Abstract

1-Substituted 1H-tetrazoles are valuable building blocks in medicinal chemistry; however, their limited synthetic accessibility constrains their use. A new continuous-flow strategy was developed to safely obtain tetrazoles from primary amines within minutes. Method optimization was aided by theoretical studies leading to different conditions depending on the amine structure. The versatility of our method was demonstrated by using a set of benzylic, aromatic, aliphatic, and heteroaromatic amines leading to previously unexplored tetrazoles with satisfactory yields.

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一步法、无催化剂连续流方法快速安全合成 1-取代的 1H 四唑

1-取代的 1H 四唑是药物化学中非常有价值的构筑基块；然而，它们有限的合成可得性限制了它们的使用。我们开发了一种新的连续流策略，可在几分钟内从伯胺中安全地获得四唑。通过理论研究，我们根据胺的结构确定了不同的条件，从而对方法进行了优化。通过使用一组苄胺、芳香胺、脂肪胺和杂芳香胺，我们以令人满意的收率制备出了以前未曾探索过的四唑，从而证明了我们方法的多样性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.