A [2 + 2] cycloaddition route to dimethylaminomethylene vinamidinium salts.
Org Lett
; 4(17): 2969-72, 2002 Aug 22.
Article
em En
| MEDLINE
| ID: mdl-12182601
ABSTRACT
[reaction see text] Trifluoropropanoic acid reacts with 1 equiv of POCl3 in DMF to generate the trifluoromethyl enamine (7). At this stage, two reaction manifolds are available. The expected reaction with additional POCl3 generates the 2-trifluoromethyl vinamidinium salt (3c). However, thermally driven loss of fluoride generates an iminium ion, which sets the stage for a [2 + 2] cycloaddition to ultimately generate the dimethylaminomethylene vinamidinium salt (1).
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Base de dados:
MEDLINE
Assunto principal:
Vimblastina
/
Dimetilaminas
/
Compostos Heterocíclicos
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article