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22.1.7.2 Thioamides (Update 2024)

DOI: 10.1055/sos-SD-122-00021

Tang, R.-Y.Science of Synthesis Knowledge Updatesearly view.

General Introduction

This is an update to the Science of Synthesis chapter on thioamides (Section 22.1.7). Thioamides are useful synthons for the synthesis of heterocycles.[‌1‌] The thioamide unit commonly exists in many bioactive molecules, agrochemicals, materials, and other functional compounds. In recent years, increasing attention has been paid to the biosynthesis and chemical application of thioamides.[‌2‌,‌3‌] Since 2004, a number of new synthetic methods for thioamides have been developed, making the synthesis of thioamides more concise and efficient.[‌4‌] To date, a variety of substrates, including amides, aldehydes, ketones, nitriles, carboxylic acids, thiocarboxylic acids, β-oxo carboxylic acids, alkynes, alkenes, oximes, benzylamines, benzyl alcohols, benzyl thiols, benzyl disulfides, active methylene precursors (such as 2-methylpyridine and the α-carbon of ketones), isothiocyanates, and thioacylation precursors have been applied to the synthesis of thioamides (Scheme 1). In these reactions, the sulfur agents can vary among Lawessons reagent, elemental sulfur, sulfide salts, phosphorus pentasulfide, thiourea, dithiophosphate, tetramethylthiuram disulfide (thiram), carbon disulfide, thiophosphoryl chloride, etc.

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