Visible-Light Photoredox Catalyzed Facile Synthesis of 2-Amino-1,3,4-Thiadiazoles from Aldehydes and Thiosemicarbazides

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC
Sachin M. Thorat, Dr. Anindita Bhowmick, Dr. Sunderraman Sambasivan, Prof. Dr. Ramakrishna G. Bhat
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引用次数: 0

Abstract

A metal-free, visible light mediated protocol has been developed to synthesize 2-amino-1,3,4-thiadiazoles (ATZ) from commercially available aldehydes and thiosemicarbazides. This one-pot strategy has been achieved by the condensation of aldehydes with substituted thiosemicarbazides in presence of 2,4,6-tri(p-tolyl)pyrylium tetrafluoroborate (TPP-TFB) as a photoredox catalyst. Different aldehydes/hetero aldehydes, as well as thiosemicarbazides reacted smoothly under the reaction conditions to afford the 2-amino-1,3,4-thiadiazoles in good to excellent yields. The practicality of the developed protocol has been successfully demonstrated by the facile one-pot synthesis of commercial herbicide Tebuthiuron on a gram scale. A series of control experiments, cyclic voltammetry, and fluorescence studies have been carried out to support the proposed reaction pathway.

Abstract Image

Abstract Image

Abstract Image

可见光光氧化还原催化醛和硫代氨基脲易降解合成2-氨基-1,3,4-噻二唑
一种无金属,可见光介导的方案已开发合成2-氨基-1,3,4-噻二唑(ATZ)从市售醛和硫代氨基脲。这种一锅策略是通过在2,4,6-三(对甲苯基)四氟硼酸吡啶(TPP-TFB)作为光氧化还原催化剂存在下,醛与取代的硫代氨基脲缩合而实现的。在反应条件下,不同醛类/杂醛类及硫代氨基脲类化合物均能顺利反应,得到收率较高的2-氨基-1,3,4-噻二唑。开发的方案的实用性已成功地通过一个简单的一锅合成的克规模的商业除草剂tebuthuron。一系列的对照实验,循环伏安法和荧光研究已经进行,以支持所提出的反应途径。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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