4.7 Article

Regioselective Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles and 1,3,4-Oxadiazoles via Alkyl 2-(Methylthio)-2-thioxoacetates and Alkyl 2-Amino-2-thioxoacetates

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 16, 页码 11486-11496

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00589

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An acid-catalyzed regioselective cyclization reaction of 2,5-disubstituted-1,3,4-thiadiazoles and 1,3,4-oxadiazoles has been developed. The precursors alkyl 2-(methylthio)-2-thioxoacetates/alkyl 2-amino-2-thioxoacetates react efficiently with acyl hydrazides, leading to a series of dehydrative and desulfurative products. Among the mentioned procedures, the alkyl 2-amino-2-thioxoacetate pathway shows excellent yield. The reported methods are operationally simplistic and highly efficient with metal-free conditions, demonstrating significant functional group compatibility. Regioselective cyclized products were confirmed by single-crystal X-ray diffraction studies.
An acid-catalyzed regioselectivecyclization reactionof 2,5-disubstituted-1,3,4-thiadiazolesand 1,3,4-oxadiazoles has been developed. The synthetic precursorsalkyl 2-(methylthio)-2-thioxoacetates/alkyl 2-amino-2-thioxoacetatesreact efficiently with acyl hydrazides, which transformed into a seriesof dehydrative and desulfurative products with employment of p-TSA and AcOH through a regioselective cyclization process.The alkyl 2-amino-2-thioxoacetate pathway generates excellent yieldamong the mentioned procedures. The reported methods are operationallysimplistic and highly efficient with metal-free conditions and demonstratesignificant functional group compatibility. Regioselective cyclizedproducts were confirmed by single-crystal X-ray diffraction studies.

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