Chemistry - A European Journal, volume 25, issue 63, pages 14284-14289

Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

Publication typeJournal Article
Publication date2019-10-17
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor4.3
ISSN09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract
A novel one-pot cascade method for the assembly of valuable NO-donor azasydnone scaffold has been developed. This construction strategy involves a diazotization/azo coupling/elimination/double rearrangement cascade sequence of readily available amines. The current protocol enables the generation of a diverse array of azasydnones, including previously hardly accessible heteroaryl substituted azasydnones (25 examples, 70-97% yield) with a good functional group tolerance under very mild conditions. Preliminary NO-releasing studies revealed an ability of azasydnones to produce NO in a wide range of concentrations. This method provides a new approach to nitrogen-oxygen heterocycles with potential applications in medicine and material science.

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GOST |
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GOST Copy
Zhilin E. S. et al. Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines // Chemistry - A European Journal. 2019. Vol. 25. No. 63. pp. 14284-14289.
GOST all authors (up to 50) Copy
Zhilin E. S., Bystrov D. M., Ananyev I. V., Fershtat L. L., Makhova N. N. Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines // Chemistry - A European Journal. 2019. Vol. 25. No. 63. pp. 14284-14289.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/chem.201903526
UR - https://doi.org/10.1002%2Fchem.201903526
TI - Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines
T2 - Chemistry - A European Journal
AU - Zhilin, Egor S
AU - Bystrov, Dmitry M.
AU - Ananyev, Ivan V
AU - Fershtat, Leonid L.
AU - Makhova, Nina N.
PY - 2019
DA - 2019/10/17 00:00:00
PB - Wiley
SP - 14284-14289
IS - 63
VL - 25
SN - 0947-6539
SN - 1521-3765
ER -
BibTex |
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BibTex Copy
@article{2019_Zhilin,
author = {Egor S Zhilin and Dmitry M. Bystrov and Ivan V Ananyev and Leonid L. Fershtat and Nina N. Makhova},
title = {Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines},
journal = {Chemistry - A European Journal},
year = {2019},
volume = {25},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002%2Fchem.201903526},
number = {63},
pages = {14284--14289},
doi = {10.1002/chem.201903526}
}
MLA
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MLA Copy
Zhilin, Egor S., et al. “Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines.” Chemistry - A European Journal, vol. 25, no. 63, Oct. 2019, pp. 14284-14289. https://doi.org/10.1002%2Fchem.201903526.
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