Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/1841

TitleDiels-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
Author(s)Alves, M. José
Durães, M. Miguel
Fortes, A. Gil
Keywords2-azadienes
2H-azirines
Diels-alder cycloaddition
Issue date2004
PublisherElsevier
JournalTetrahedron
Citation"Tetrahedron". 60 (2004) 6541-6553.
Abstract(s)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 C=N 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.
TypeArticle
URIhttp://hdl.handle.net/1822/1841
DOI10.1016/j.tet.2004.06.004
ISSN0040-4020
Peer-Reviewedyes
AccessOpen access
Appears in Collections:CDQuim - Artigos (Papers)

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