American Chemical Society
jo2c01969_si_001.pdf (3.07 MB)

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

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journal contribution
posted on 2023-01-24, 18:21 authored by Zhi-Wei Xi, Yan He, Li-Qiu Liu, Ying-Chun Wang, Hui-Ying Zeng
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-3-one 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.