Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity

Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity

Treatment of 1-(2-oxiranylmethyl)-4,5,6,7-tetrahydroindole with the DMF/(COCl)2 reagent system in CH2Cl2 (room temperature, 40min) starts oxirane opening to give 1-(3-chloro-2-hydroxypropyl)-4,5,6,7-tetrahydroindole followed by the formylation of the pyrrole ring to end up with the formation of 1-(3...

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Veröffentlicht in:Mendeleev communications 2012-09, Vol.22 (5), p.265-266
Hauptverfasser: Ivanov, Andrei V., Ushakov, Igor A., Markova, Marina V., Falicheva, Svetlana Yu, Mikhaleva, Al’bina I., Trofimov, Boris A.
Format: Artikel
Sprache:eng
Schlagworte:
Oxirane
Pyrroles
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Zusammenfassung:Treatment of 1-(2-oxiranylmethyl)-4,5,6,7-tetrahydroindole with the DMF/(COCl)2 reagent system in CH2Cl2 (room temperature, 40min) starts oxirane opening to give 1-(3-chloro-2-hydroxypropyl)-4,5,6,7-tetrahydroindole followed by the formylation of the pyrrole ring to end up with the formation of 1-(3-chloro-2-formyloxypropyl)-4,5,6,7-tetrahydroindole-2-carboxaldehyde viathe intermediate 1-(3-chloro-2-hydroxypropyl)-4,5,6,7-tetrahydroindole-2-carboxaldehyde.
ISSN:0959-9436
DOI:10.1016/j.mencom.2012.09.013