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Réactivité des N -vinylaziridines fonctionnalisées. Synthèse de dérivés des α,β-déhydro α-amino acides

1982; NRC Research Press; Volume: 60; Issue: 22 Linguagem: Inglês

10.1139/v82-406

1480-3291

Yvonne Gelas‐Mialhe, Evelyne Touraud, R. VESSIERE,

Synthesis and Biological Activity

Secondary 2-cyano- and 2-ethoxycarbonylaziridines react with acetylenic compounds and activated vinylic chlorides to give 2-cyano and 2-ethoxycarbonyl N-vinylaziridines. The nucleophile-catalysed isomerization of these compounds generally gives α,β-dehydro α-amino acid derivatives involving nucleophilic attack at C-3. Thermal isomerization, involving predominantly cleavage of the carbon–carbon bond of the ring, forms α-vinylamino esters and nitriles.