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The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents

Maria Evgenievna Chizhova 1
Maria Evgenievna Chizhova
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
, 
Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2020.07.030
Published 2020-06-26
Communication , Volume 30, Issue 4, 496-497
3
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Chizhova M. E., Dar’in D. V., Krasavin M. Y. The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 496-497.
GOST all authors (up to 50) Copy
Chizhova M. E., Dar’in D. V., Krasavin M. Y. The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 496-497.
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TY - JOUR
DO - 10.1016/j.mencom.2020.07.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.030
TI - The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents
T2 - Mendeleev Communications
AU - Chizhova, Maria Evgenievna
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 496-497
IS - 4
VL - 30
ER -
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@article{2020_Chizhova,
author = {Maria Evgenievna Chizhova and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.030},
number = {4},
pages = {496--497},
doi = {10.1016/j.mencom.2020.07.030}
}
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Chizhova, Maria Evgenievna, et al. “The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 496-497. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.030.

Keywords

Castagnoli–Cushman reaction
cyclic anhydrides
enolization
imines
resonance stabilization
δ-lactams

Abstract

Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from the mechanistic perspective.

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