54600-29-2Relevant articles and documents
Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y
Thierry, Thibault,Pfund, Emmanuel,Lequeux, Thierry
supporting information, p. 14826 - 14830 (2021/10/01)
A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.
An approach to some spiro oxindole alkaloids through cycloaddition reactions of 3-methylideneindolin-2-one
Bell, Stephanie E. V.,Brown, Roger F.C.,Eastwood, Frank W.,Horvath, Julianna M.
, p. 183 - 190 (2007/10/03)
3-Methylideneindolin-2-one (3-methylideneoxindole) (1) was prepared in 60-89% yield by flash vacuum pyrolysis of the acetate or methyl carbonate of 3-hydroxy-3-methylindolin-2-one, and was fully characterized, but application of the same procedure to 3-hydroxy-5-methoxyindolin-2-one did not give useful yields. Cycloaddition reactions of CH2=+NR-CH2- and of the related ylide (25) (from 1-(trimethylsilylmethyl)piperidine-2-carbonitrile and AgF) to 3-methylideneindolin-2-one (1) gave 4-20% yields of spiro oxindoles, but yields were markedly below those achieved in cycloadditions to the more electrophilic N-phenylmaleimide (70-79%). Attempted alkylation of weakly basic secondary amines, e.g. piperidine-2-carbonitrile, with Me3SiCH2Cl in dimethyl sulfoxide/K2CO3 gave only carbamates Me3SiCH2OOCNR2. CSIRO 2000.
