Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/1841
Título: | 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 |
Autor(es): | Alves, M. José Durães, M. Miguel Fortes, A. Gil |
Palavras-chave: | 2-azadienes 2H-azirines Diels-alder cycloaddition |
Data: | 2004 |
Editora: | Elsevier 1 |
Revista: | Tetrahedron |
Citação: | "Tetrahedron". 60 (2004) 6541-6553. |
Resumo(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. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/1841 |
DOI: | 10.1016/j.tet.2004.06.004 |
ISSN: | 0040-4020 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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MigFullPaperV2.pdf | 166,17 kB | Adobe PDF | Ver/Abrir |