DMSO/SOCl2 was found to be an effective system for the intramolecular cyclization of 2‐alkynylbenzoates or 2‐alkynylbenzoic acids, which can afford biologically interesting 4‐(methylthio)isochromenones through regioselective electrophilic 6‐endo‐dig cyclization. DMSO plays the roles of both solvent and sulfur source and can also be replaced with its deuterated counterpart [D6]DMSO, enabling the incorporation of the SCD3 moiety into the isochromenone skeleton.
A series of C3‐unsymmetric spirooxindoles were achieved by reaction of diphenylmalonamides with PhI(OAc)2 (PIDA) under metal‐free conditions. Control experiments suggest that the hypervalent iodine‐mediated reaction undergoes a cascade process involving an oxidative C−C bond formation preceeding an oxidative C−N bond formation.magnified image
The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.
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