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

Abstract

The three-component domino reaction of thioamides, benzyl isocyanide, and water in the presence of a catalytic amount of both Pd(dppf)Cl 2 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 openchain products. This divergent reaction enabled the one-pot construction of five (N−

Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

“…Various nucleophiles including carbon, oxygen, nitrogen, and sulfur atoms, are widely used in the synthesis of heterocyclic skeletons (Scheme 1a). 13 In this regard, reactions involving a nitrogen atom mainly including amino and amide groups were extensively studied. However, relatively little research has been conducted on the exploration of nitrogen in aziridine combined with isocyanide.…”

A Three‐Component Domino Reaction Enabled by Phase‐Transfer Catalysis for the Assembly of 3‐Thioquinoline‐2,5‐Diones

“…[3] On the other hand, multicomponent domino reactions (MDRs) are concise and convergent transformations that involve three or more readily accessible substrates, and enable the simultaneous formation of two or more chemical bonds that depend on the functionalities produced in the preceding step and do not require the isolation of probable intermediates. [4] In a broad sense, MDRs constitute an exquisite subset within the onepot-reaction family. [5] During the past few decades, MDRs have evolved significantly with regard to both status and practice, and have found extensive use in creating libraries of valuable molecules, such as lead compounds, natural-product mimics, and chemical probes.…”