Wiley
Advanced Synthesis and Catalysis
,  volume 360 ,  issue 16 ,  pages 3157-3163

Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates

Dmitry M. Bystrov 1, 2, 3, 4
, 
Egor S Zhilin 1, 2, 3, 4
, 
Leonid L. Fershtat 1
, 
Anna A Romanova 5, 6, 7, 8
, 
Ivan V Ananyev 5
, 
Nina N. Makhova 1
1
 
2
 
3
 
4
 
5
 
6
 
7
 
8
 
Publication type: Journal Article
Publication date: 2018-06-27
Wiley
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract

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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Found 
Found 
12 citations
Fershtat Leonid
DSc in Chemistry
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h-index: 29
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
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h-index: 30
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A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
National Research University Higher School of Economics
National Research University Higher School of Economics
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Larin Alexander
PhD in Chemistry
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h-index: 16
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
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N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
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Saint Petersburg State University
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Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
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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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
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.