20357-06-6Relevant academic research and scientific papers
Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner-Meerwein Type 1,2-Amide Migration of 2-Spiropseudoindoxyls
Marien, Niels,Luo, Ting,Verniest, Guido
, p. 934 - 938 (2017)
Spiropseudoindoxyls were synthesized by using a gold(III)-catalyzed intramolecular nitroalkyne redox-dipolar cycloaddition cascade. These compounds were then transformed into novel piperidinone and azepanone fused indoles via a straightforward hydrogenation. The reaction mechanism of this ring expansion is believed to proceed through a rare Wagner-Meerwein type 1,2-amide migration.
Synthesis of 2-spiropseudoindoxyls via an intramolecular nitroalkyne redox-dipolar cycloaddition cascade
Marien, Niels,Brigou, Ben,Pinter, Balazs,De Proft, Frank,Verniest, Guido
, p. 270 - 273 (2015/03/05)
Novel spiropseudoindoxyls were synthesized in high yields via a fully regioselective Au(III)-catalyzed cycloisomerization of easily obtainable o-nitrophenylpropiolamides, followed by an intramolecular dipolar cycloaddition as key steps. This one-pot cascade reaction resulted in new tetracyclic pseudoindoxyls, which were hydrogenated toward the title compounds as single diastereomers via N-O cleavage. The mechanism of the gold catalyzed cycloisomerization was studied by DFT and suggests a reaction path without the intermediacy of gold carbenoid species in these cases.
