16895-58-2Relevant articles and documents
Carbonyl 1,2-transposition through triflate-mediated a-amination
Wu, Zhao,Xu, Xiaolong,Wang, Jianchun,Dong, Guangbin
, p. 734 - 740 (2021/11/16)
To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.
Enamino Ketones as Precursors of Functionalised 2H-Thiopyrans and Thiopyrano- and -benzothiopyrans
Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark
, p. 2603 - 2608 (2007/10/02)
Oxo enamino ketones obtained by treating active methylene compounds with N,N-dimethylformamide dimethyl acetal yield novel 2H-thiopyrans in a regioselective one pot thionation--cycloaddition sequence.Application of similar methodology to thiochroman-3-ones affords novel thiopyranobenzothiopyrans and the isomers.
Metalation reactions XIII. The reactions of electrophiles with the dilithiated species 1-(α-lithiomethyl)-2-benzene
Cabiddu, S.,Floris, C.,Gelli, G.,Melis, S.
, p. 1 - 10 (2007/10/02)
Direct dimetalation of 1-methyl-2-(methylthio)benzene (1) gives the dilithiated species (2) in good yield, which can be used to introduce substituents into the thiomethyl and methyl groups.Species 2 can react also with a variety of dichlorosilanes and dichlorostannanes, and with sulphur chloride, to yield derivatives of 1,3-benzothiasilin, 1,3-benzothiastannin and 1,3-benzodithiin respectively.Reaction of 2 with tetrachlorosilane yields a spirocyclic silicon compound, while reaction with benzoyl chloride yields a derivative of 1-benzothiopyran.