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Reactions 1‐acetyl‐3‐oxo‐2,3‐dihydroindole with alkyl 2‐cyano‐3‐alkoxypropenoate and alkyl 2‐alkoxycarbonyl‐3‐alkoxy‐propenoate. Synthesis of 9‐acetoxypyrrolo[1,2‐ a ]indol‐3‐one derivatives
Author(s) -
Mérour J. Y.,
Piroëlle S.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280812
Subject(s) - chemistry , acetic anhydride , alkyl , sodium hydride , alkoxy group , medicinal chemistry , organic chemistry , acetylation , catalysis , biochemistry , gene
1‐Acetyl‐3‐oxo‐2,3‐dihydroindole reacted with methyl 2‐cyano‐3‐methoxypropenoate and ethyl 2‐cyano‐3‐ethoxypropenoate in the presence of sodium hydride, affording compounds 3 (2‐(2‐cyano‐2‐alkoxycarbonyl‐vinyl)‐3‐hydroxyindole). Methyl 2‐methoxycarbonyl‐3‐methoxypropenoate gave compounds 4 or compounds 5 (in the presence of Triton B). Heating compounds 3 or their acetylated derivatives in acetic anhydride at reflux afforded 9‐acetoxy‐(3 H )‐pyrrolo[1,2‐ a ]indol‐3‐one 8 .