Mono-fluorinated benzoylacetanilides in the synthesis of heterocycles

350

P82

Mono-fluorinated benzoylacetanilides in the synthesis of heterocycles Maria Burgiel and Anna Kolasa Departof Organic Chemistry, Faculty of Chemistry, Jagielkmian R. Ingardem 3, 30-060 Cracow (Polanxi~

University,

Fluorine-containing anilines and ethyl benzoylacetate give monofluorinated benzoylacetanilides. These react easily with formaldehyde to yield the fluorinated dianilides of 2,4-dibenzoylpentanedioic acid, which can be simply converted, under the influence of excess POCla, to I-monofluorophenyl-3benzoyl-1,2,3,4-tetrahydroindeno[ 1,2-blpyridine-2,5-dione.

HCHO

c&&J / &\

F

DOCl3 -

F-c6~4-NH2

~O-&NH-&

QCO-t~~CO.NH~

- Ii*0

This efficient one-step synthesis of a fused heterocyclic system (present in many Annonaceae alkaloids) starting from open-chain compounds, provides fluorine derivatives that are expected to have potential biological activity.