30264-74-5Relevant academic research and scientific papers
Photoinduced and N-bromosuccinimide-mediated cyclization of 2-azido-N-phenylacetamides
Li, Zhan-Shan,Wang, Wei-Xia,Yang, Ji-Dong,Wu, Yue-Wei,Zhang, Wei
supporting information, p. 3820 - 3823 (2013/09/02)
An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1, 2′-imidazol]-4′-ones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2′-imidazol]-4′-ones are obtained as the main products when the substrates bear electron-donating groups at the para-position.
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.
