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2004
Indole derivatives
R 0140
A Nucleophilic Addition of Acetone Enolate to (E)-Alkyloxindolylideneacetates.
The base-catalyzed condensation of title acetates (I) with acetone (II) affords the
44- 124 —
pentanoic acid esters (III) as an inseparable mixture of diastereomers. In the case of
morpholine as the base, the unexpected spiro compound (VI) is detected. Methylation
of (III) in acetone yields the methylated products (V) as a separable mixture of diastereomers. The same reaction applied to (I) furnishes the N-methylated product (VII)
accompanied by the unexpected dispiro compound (VIII) and one of the two diastereomers formed in the reaction (III)→(V). — (OSMAN*, F. H.; EL-SAMAHY, F. A.;
FARAG, I. S. A.; Monatsh. Chem. 135 (2004) 7, 823-831; Dep. Pestic. Chem., Natl.
Res. Cent., Dokki, Cairo 12622, Egypt; Eng.) — H. Hoennerscheid
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