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一种无色谱的一锅两步法,在无溶剂条件下由伯酰胺经硫醇化和氧化二聚反应合成1,2,4-噻二唑:一种更绿色的方法。

A chromatography-free one-pot, two-step synthesis of 1,2,4-thiadiazoles from primary amides thiolation and oxidative dimerization under solvent-free conditions: a greener approach.

作者信息

Rajput Khushbu, Singh Vishal, Singh Sundaram, Srivastava Vandana

机构信息

Department of Chemistry, Indian Institute of Technology (BHU) Varanasi-221005 India

出版信息

RSC Adv. 2024 Jul 16;14(31):22480-22485. doi: 10.1039/d4ra03993a. eCollection 2024 Jul 12.

DOI:10.1039/d4ra03993a
PMID:39015666
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11250125/
Abstract

An efficient and practical one-pot, two-step synthesis of 1,2,4-thiadiazoles from primary amides with Lawesson reagent (LR) and -butyl hydrogen peroxide (TBHP) without solvent is demonstrated for the first time. This groundbreaking and environmentally friendly approach utilises readily available starting materials and eliminates the use of traditional solvents in the reaction process. The broad substrate scope, excellent functional group tolerance in mild and metal-free conditions, quick conversion, and excellent yields are essential features of this methodology. All the compounds were purified without column chromatography.

摘要

首次展示了一种高效实用的一锅两步法,在无溶剂条件下,由伯酰胺与劳森试剂(LR)和叔丁基过氧化氢(TBHP)合成1,2,4-噻二唑。这种开创性的环保方法使用了易得的起始原料,并在反应过程中避免了传统溶剂的使用。该方法的重要特点包括底物范围广、在温和且无金属的条件下对官能团具有出色的耐受性、快速转化以及高收率。所有化合物无需柱色谱法即可纯化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/df9559a12a53/d4ra03993a-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/466f51cd6ec5/d4ra03993a-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/74c02ca81d70/d4ra03993a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/b10209f9d53e/d4ra03993a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/f2b87296e030/d4ra03993a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/df9559a12a53/d4ra03993a-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/466f51cd6ec5/d4ra03993a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/5d345bbb79b3/d4ra03993a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/498dee86d647/d4ra03993a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/74c02ca81d70/d4ra03993a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/b10209f9d53e/d4ra03993a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/f2b87296e030/d4ra03993a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa7e/11250125/df9559a12a53/d4ra03993a-s7.jpg

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本文引用的文献

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Iodide-promoted transformations of imidazopyridines into sulfur-bridged imidazopyridines or 1,2,4-thiadiazoles.碘促进的咪唑并吡啶转化为硫桥联咪唑并吡啶或 1,2,4-噻二唑。
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微波辅助催化法直接从胺和羧酸绿色合成酰胺
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