A. V. Ivanov, I. A. Ushakov, M. V. Markova, S. Yu. Falicheva, A. I. Mikhaleva, B. A. Trofimov, “Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity”, Mendeleev Commun., 2012, Volume 22, Issue 5,Pages 265

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

A. V. Ivanov, I. A. Ushakov, M. V. Markova, S. Yu. Falicheva, A. I. Mikhaleva, B. A. Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Abstract: 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.

Language: English

DOI: 10.1016/j.mencom.2012.09.013