A [2 + 2] cycloaddition route to dimethylaminomethylene vinamidinium salts.
Org Lett
; 4(17): 2969-72, 2002 Aug 22.
Article
in 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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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Vinblastine
/
Dimethylamines
/
Heterocyclic Compounds
Language:
En
Journal:
Org Lett
Year:
2002
Document type:
Article