148518-74-5Relevant academic research and scientific papers
Effects of catalysts on the cyclization of 2-diazo-2-methoxycarbonyl-N-aryl-N-alkylethanamides
Smith, Keith,Bahzad, Dawoud
, p. 2793 - 2798 (2007/10/03)
Inorganic solids have pronounced effects on the product distribution from decomposition of the title compounds; zeolite Kβ is particularly useful for directing the synthesis of indolinones such as 5-methoxy-N-methylindolin-2-one, which is formed in 89% yield from 2-diazo-2-methoxycarbonyl-N-(4-methoxyphenyl)-N-methylethanamide; speculation is made about a possible mechanism.
The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.
Wee, Andrew G.,Liu, Baosheng
, p. 609 - 626 (2007/10/02)
Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields.Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization.In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives.It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.
