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

, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Marina Victorovna Markova 1
Marina Victorovna Markova
, 
Svetlana Yu Falicheva 1
Svetlana Yu Falicheva
, 
Albina Ivanovna Mikhaleva 1
Albina Ivanovna Mikhaleva
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2012.09.013
Published 2012-09-17
Communication , Volume 22, Issue 5, 265-266
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Ivanov A. V. et al. Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity // Mendeleev Communications. 2012. Vol. 22. No. 5. pp. 265-266.
GOST all authors (up to 50) Copy
Ivanov A. V., Ushakov I. A., Markova M. V., Falicheva S. Yu., Mikhaleva A. I., Trofimov B. A. Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity // Mendeleev Communications. 2012. Vol. 22. No. 5. pp. 265-266.
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TY - JOUR
DO - 10.1016/j.mencom.2012.09.013
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.013
TI - Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity
T2 - Mendeleev Communications
AU - Ivanov, Andrey Viktorovich
AU - Ushakov, Igor Alekseevich
AU - Markova, Marina Victorovna
AU - Falicheva, Svetlana Yu
AU - Mikhaleva, Albina Ivanovna
AU - Trofimov, Boris Aleksandrovich
PY - 2012
DA - 2012/09/17
PB - Mendeleev Communications
SP - 265-266
IS - 5
VL - 22
ER -
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@article{2012_Ivanov,
author = {Andrey Viktorovich Ivanov and Igor Alekseevich Ushakov and Marina Victorovna Markova and Svetlana Yu Falicheva and Albina Ivanovna Mikhaleva and Boris Aleksandrovich Trofimov},
title = {Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.013},
number = {5},
pages = {265--266},
doi = {10.1016/j.mencom.2012.09.013}
}
MLA
Cite this
MLA Copy
Ivanov, Andrey Viktorovich, et al. “Regioselective Formylation of 1-(2-Oxiranylmethyl)-4,5,6,7-tetrahydroindole with DMF/(COCl)2: the Pyrrole vs. Oxirane Nucleophilicity.” Mendeleev Communications, vol. 22, no. 5, Sep. 2012, pp. 265-266. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.09.013.

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.

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