93641-74-8Relevant articles and documents
Intermolecular cyclotrimerization of haloketoalkynes and internal alkynes: Facile access to arenes and phthalides
Silvestri,Oakdale
supporting information, p. 13417 - 13420 (2020/11/10)
A highly chemo-and regioselective cyclo(co)trimerization between 3-halopropiolamides and symmetrical internal alkynes is reported. The reaction is catalyzed by CpRuCl(COD) and proceeds under air at ambient temperature in ethanol with no additional precautions. Iodo-, bromo-, and chloropropiolamides, esters, and ketones are viable coupling partners and, in a 2?:?1 stoichiometry relative to internal alkyne, yield fully-substituted arenes in a single step. The highest regioselectivities (96% single isomer) were observed when employing 2° and 3°-halopropiolamides. A mechanistic hypothesis accounting for this selectivity is proposed. Notably, by using 1,4-butynediol as the internal alkyne, in situ lactonization following [2+2+2]-cycloaddition generates therapeutically-relevant phthalide pharmacophores directly. This journal is
Dithio and Thiono Esters, 50. - α,β-Acetylenic Thioamides, Dithio Esters, and Thiono Esters
Hartke, Klaus,Gerber, Hans-Dieter,Roesrath, Ulrich
, p. 903 - 916 (2007/10/02)
α,β-Acetylenic amides 5 and thioamides 7 have been obtained by a palladium-catalysed condensation of the terminal acetylenes 3 with N,N-dimethylcarbamoyl chloride (4) or -thiocarbamoyl chloride (6).Sulfhydrolysis of the α,β-acetylenic thioamidium salts 19
