172095-47-5Relevant academic research and scientific papers
Diels-Alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)- 2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1. 0]heptane-6-carboxylates
Alves, M. José,Dur?es, M. Miguel,Fortes, A. Gil
, p. 6541 - 6553 (2007/10/03)
A number of fused 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates, a new type of compound, have been obtained by Diels-Alder cycloaddition between nucleophilic 2-azadienes and an electrophilic 2H-azirine. The reactions are completely endo- and regioselective, the azirine being added by its less hindered face to the diene. There are two isomers 7 and 8 formed from dienes 1 due either to isomerization of the cycloadducts 7 and 8 or by isomerization of the CN bond of the diene during the reaction. The isomer 10 is formed from diene 2e, and a single diastereoisomer structure 4a-i is formed from dienes 11. Some pyrimidones 8a, 7c/8c, 7e, 10, 11d have been hydrolyzed leading to functionalised aziridines 12, 13 and 15.
2-Aza-1,3-Dienes: Methods of Synthesis and Stereochemical Studies
Ghosez, L.,Bayard, Ph.,Nshimyumukiza, P.,Gouverneur, V.,Sainte, F.,et al.
, p. 11021 - 11042 (2007/10/02)
2-Aza-1,3-dienes bearing an activating trialkylsilyloxy group at C-3 have been prepared via three routes.The first route involves the silylation of N-acylimidates which are readily available from iminoether hydrochlorides and acid chlorides.According to a more general route towards these doubly activated dienes, N-trialkylsilylimidates and N-trialkylsilylimines derived from non-enolizable aldehydes were conveniently converted in a one-pot sequence into the corresponding azadienes by reaction with an acid chloride in the presence of triethylamine.Finally, cyclic dienes could be prepared by direct silylation of glutarimide on both oxygens with trialkylsilyltriflate in the presence of triethylamine.The configuration and conformation of 2-azadienes have been established by 1H, 13C and 15N NMR spectroscopy.
