102235-83-6Relevant academic research and scientific papers
Cycloadditions, 15. - Influence of Substituents in p-, m-, and o-Position of the Arene onto the Intramolecular Diels-Alder Reaction of Allenecarboxylic Acid Anilides and Phenyl Esters
Himbert, Gerhard,Fink, Dieter,Diehl, Klaus,Rademacher, Paul,Bittner, Andreas J.
, p. 1161 - 1174 (2007/10/02)
The ylides 3 and 8 (synthesized via the bromoacetic acid amides 1 and -esters 6 and via the phosphonium bromides 2 and 7) react with ketene to give the allenecarboxanilides 4 and the phenyl allenecarboxylates 9.Thermolysis in boiling xylene of all derivat
Cycloadditions, 7. Intramolecular Diels-Alder Reactions of Allenecarboxanilides; Variation of the Substituents in the p-Position of the Aniline Nucleus
Diehl, Klaus,Himbert, Gerhard,Henn, Lothar
, p. 2430 - 2443 (2007/10/02)
The N-methyl-1,2-propadiene-1-carboxanilides 6a-h, differently substituted in the p-position, are synthesized by Wittig reaction of the carbamoylmethylenephosphoranes 5 with ketene.They isomerize by thermolysis in boiling xylene to give the tricycles 7a-h, the products of the intramolecular Diels-Alder reaction, and in some cases also to the quinolones 9, the products of a cyclization reaction.The order of the reaction and the influence of the substituents upon the rate of the intramolecular Diels -Alder reaction are determined by 1H-NMR spectroscopy.
