Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates
Тип публикации: Journal Article
Дата публикации: 2018-06-27
scimago Q1
wos Q1
БС1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Краткое описание
A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2‐aminohetarene N‐oxides was developed. The developed reaction is suitable for both five‐ and six‐membered heterocycles and proceeds through the condensation of 2‐aminohetarene N‐oxide with trimethyl orthoformate followed by intramolecular N‐oxide oxygen transfer. For five‐membered hetarene N‐oxides (furoxans), the intramolecular rearrangement is catalyzed by a cyanide anion, while for six‐membered hetarene N‐oxides (azines), Lewis acid catalysis is sufficient. The developed protocol is characterized by operational simplicity and high efficiency, resulting in carbamoyl derivatives in good and high yields.
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Bystrov D. M. et al. Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates // Advanced Synthesis and Catalysis. 2018. Vol. 360. No. 16. pp. 3157-3163.
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Bystrov D. M., Zhilin E. S., Fershtat L. L., Romanova A. A., Ananyev I. V., Makhova N. N. Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates // Advanced Synthesis and Catalysis. 2018. Vol. 360. No. 16. pp. 3157-3163.
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TY - JOUR
DO - 10.1002/adsc.201800407
UR - https://onlinelibrary.wiley.com/doi/10.1002/adsc.201800407
TI - Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates
T2 - Advanced Synthesis and Catalysis
AU - Bystrov, Dmitry M.
AU - Zhilin, Egor S
AU - Fershtat, Leonid L.
AU - Romanova, Anna A
AU - Ananyev, Ivan V
AU - Makhova, Nina N.
PY - 2018
DA - 2018/06/27
PB - Wiley
SP - 3157-3163
IS - 16
VL - 360
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2018_Bystrov,
author = {Dmitry M. Bystrov and Egor S Zhilin and Leonid L. Fershtat and Anna A Romanova and Ivan V Ananyev and Nina N. Makhova},
title = {Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates},
journal = {Advanced Synthesis and Catalysis},
year = {2018},
volume = {360},
publisher = {Wiley},
month = {jun},
url = {https://onlinelibrary.wiley.com/doi/10.1002/adsc.201800407},
number = {16},
pages = {3157--3163},
doi = {10.1002/adsc.201800407}
}
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MLA
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Bystrov, Dmitry M., et al. “Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates.” Advanced Synthesis and Catalysis, vol. 360, no. 16, Jun. 2018, pp. 3157-3163. https://onlinelibrary.wiley.com/doi/10.1002/adsc.201800407.