72377-93-6Relevant articles and documents
Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids
Kumar, Nivesh,Das, Mrinal Kanti,Ghosh, Santanu,Bisai, Alakesh
supporting information, p. 2170 - 2173 (2017/02/19)
We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.
Photostimulated Reactions of N,N-Disubstituted Amide Enolate Anions with Haloarenes by the SRN1 Mechanism in Liquid Ammonia
Rossi, Roberto A.,Alonso, Ruben A.
, p. 1239 - 1241 (2007/10/02)
The photostimulated reactions of chloro-, bromo-, and iodobenzenes, 1-chloronaphthalene, and 9-bromophenanthrene with the enolate anion of N-methyl-N-phenylacetamide in liquid ammonia gave good yields of substituted products.In the dark, iodobenzene gave 34percent of substitution product, but chlorobenzene did not react.The enolate anion of N,N-dimethylacetamide was only partially soluble in liquid ammonia, but good yields of substitution products were obtained.The enolate anion of N-acetylpiperidine was insoluble in liquid ammonia, but the enolate anion of N-acetylmorpholine was soluble and good yields of substitution products were obtained under photostimulation.It is suggested that these reactions occur by the SRN1 mechanism of aromatic substitution.
