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Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative

Mikhail Mikhailovich Vinogradov 1
Mikhail Mikhailovich Vinogradov
, 
Daria Vladimirovna Vorobyeva 1
Daria Vladimirovna Vorobyeva
,  , 
Sergey Nikolaevich Osipov 1, 2
Sergey Nikolaevich Osipov
, 
Dmitry Alexandrovich Loginov 1, 3
Dmitry Alexandrovich Loginov
10.1016/j.mencom.2020.07.029
Published 2020-06-26
Communication , Volume 30, Issue 4, 494-495
3
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Vinogradov M. M. et al. Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 494-495.
GOST all authors (up to 50) Copy
Vinogradov M. M., Vorobyeva D. V., Nelyubina Y. V., Osipov S. N., Loginov D. A. Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 494-495.
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TY - JOUR
DO - 10.1016/j.mencom.2020.07.029
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.029
TI - Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative
T2 - Mendeleev Communications
AU - Vinogradov, Mikhail Mikhailovich
AU - Vorobyeva, Daria Vladimirovna
AU - Nelyubina, Yulia Vladimirovna
AU - Osipov, Sergey Nikolaevich
AU - Loginov, Dmitry Alexandrovich
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 494-495
IS - 4
VL - 30
ER -
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@article{2020_Vinogradov,
author = {Mikhail Mikhailovich Vinogradov and Daria Vladimirovna Vorobyeva and Yulia Vladimirovna Nelyubina and Sergey Nikolaevich Osipov and Dmitry Alexandrovich Loginov},
title = {Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.029},
number = {4},
pages = {494--495},
doi = {10.1016/j.mencom.2020.07.029}
}
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Vinogradov, Mikhail Mikhailovich, et al. “Unusual multiple insertion of diazo carbonyl compounds into (purin-6-yl)benzene derivative.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 494-495. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.029.

Keywords

C–H functionalization
carbenoids
diazo compounds
homogeneous catalysis
nitrogen heterocycles
organofluorine compounds
purines

Abstract

The consecutive alkylation of 9-isopropyl-6-phenyl-9H-purine with methyl 2-diazo-3,3,3-trifluoropropionate and diethyl diazomalonate proceeds at the phenyl substituent firstly via ortho-C–H activation under chelation-assistance of the purine core, followed by classical electrophilic metal carbenoid insertion to the C−H bond of a malonate moiety.

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