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Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-az...

Alves, M. José; Durães, M. Miguel; Fortes, A. Gil

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 ...


Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to elect...

Alves, M. José; Durães, M. Miguel; Fortes, A. Gil

Tert-Butyldimethylsililoxy-2-aza-1,3-butadienes react with 2H-azirine 3 leading to Diels-Alder cycloadducts in moderate yields. The reactions are endo- and regio- selective with the azirine being added by its less hindered face. There is only one product in the case of 1b, 4b. There are two isomers (4 and 5) from 1a, 1c and 1d. A different result was obtained with the diene 1e. Diene 1e formed products 4e and 8...


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