Journal of Organic Chemistry, volume 86, issue 5, pages 4098-4111
Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds
Publication type: Journal Article
Publication date: 2021-02-11
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
The reaction conditions for the Buchner reaction of 2-(diazoacetyl)-2H-azirines with benzene leading to 2-(cyclohepta-2,4,6-trien-1-yl)-2H-azirines have been found. The azirine fragment of these compounds was subsequently used to prepare 5-(cyclohepta-2,4,6-trien-1-yl)isoxazoles and α-(cyclohepta-2,4,6-triene-1-ylcarbonyl)-1H-pyrroles. NMR and DFT calculations showed that the cycloheptatriene-norcaradiene valence isomerization in the corresponding moieties of synthesized azirines, isoxazoles, and pyrroles is very fast at room temperature. Cycloheptatriene valence isomer predominates in azirines and pyrroles, while 5-(cycloheptatrienyl)isoxazoles exist in a pure cycloheptatriene form at 25 °C in chloroform solution. In accordance with the X-ray analysis, two of the synthesized pyrroles crystallized as norcaradiene isomers from a solution of equilibrium mixture of valence isomers. Reductive isoxazole ring opening using the Mo(CO)6/H2O reductive system afforded (Z)-3-amino-3-aryl-1-(cyclohepta-2,4,6-trien-1-yl)prop-2-en-1-ones, which are pure cycloheptatriene isomers. α-(Cycloheptatrieneylcarbonyl)-1H-pyrroles were transformed into the α-(benzylcarbonyl)-1H-pyrroles under cooperative TFA/Rh2(TFA)4 catalysis.
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Galenko E. E. et al. Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds // Journal of Organic Chemistry. 2021. Vol. 86. No. 5. pp. 4098-4111.
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Galenko E. E., Bodunov V. A., Kryukova M. A., Novikov M. S., Khlebnikov A. F. Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds // Journal of Organic Chemistry. 2021. Vol. 86. No. 5. pp. 4098-4111.
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TY - JOUR
DO - 10.1021/acs.joc.0c02928
UR - https://doi.org/10.1021%2Facs.joc.0c02928
TI - Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds
T2 - Journal of Organic Chemistry
AU - Galenko, Ekaterina E
AU - Bodunov, Vladimir A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Kryukova, Mariya A
PY - 2021
DA - 2021/02/11 00:00:00
PB - American Chemical Society (ACS)
SP - 4098-4111
IS - 5
VL - 86
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Galenko,
author = {Ekaterina E Galenko and Vladimir A Bodunov and Mikhail S. Novikov and Alexander F Khlebnikov and Mariya A Kryukova},
title = {Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021%2Facs.joc.0c02928},
number = {5},
pages = {4098--4111},
doi = {10.1021/acs.joc.0c02928}
}
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Galenko, Ekaterina E., et al. “Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds.” Journal of Organic Chemistry, vol. 86, no. 5, Feb. 2021, pp. 4098-4111. https://doi.org/10.1021%2Facs.joc.0c02928.