Three-Component Domino Reaction of Thioamide, Isonitriles, and Water: Selective Synthesis of 1,2,4-Thiadiazolidin-3-ones and (E)-N-(1,2-Diamino-2-thioxoethylidene)benzamides

被引：4

作者：

Xi, Zhi-Wei ^{[1
]}

He, Yan ^{[2
]}

Liu, Li-Qiu ^{[1
]}

Wang, Ying-Chun ^{[1
]}

Zeng, Hui-Ying ^{[3
]}

机构：

[1] Jishou Univ, Natl Demonstrat Ctr Expt Chem Educ, Hunan Engn Lab Anal & Drugs Dev Ethnomed Wuling Mt, Jishou 416000, Peoples R China

[2] Xuzhou Univ Technol, Sch Mat & Chem Engn, Xuzhou 221018, Peoples R China

[3] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 12期

基金：

中国国家自然科学基金;

关键词：

C-H; CATALYSIS; METAL; MULTICOMPONENT; ISOCYANIDES; STRATEGY; COMBINATION; INSERTION; ENZYMES;

D O I：

10.1021/acs.joc.2c01969

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three-component domino reaction of thioamides, benzyl isocyanide, and water in the presence of a catalytic amount of both Pd(dppf)Cl2 and Cu(OAc)2 afforded novel 1,2,4-thiadiazolidin-3one cyclic compounds, whereas the same reaction with tertiary alkylisonitriles in the presence of rare earth metal salt [La(OTf)3] resulted in (E)-N-(1,2-diamino-2-thioxoethylidene)benzamide open chain products. This divergent reaction enabled the one-pot construction of five (N-S, C-S, C-O, and two C-N) or four (C- S, C-N, C-O, and C-C) new chemical bonds. Mechanism studies indicate that the oxygen atom of the product was derived from H2O.

引用

页码：8315 / 8325

页数：11

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