Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines
Egor S Zhilin
1, 2
,
Dmitry M. Bystrov
1, 2
,
Ivan V Ananyev
3, 4
,
Leonid L. Fershtat
1, 2
,
Nina N. Makhova
1, 2
Publication type: Journal Article
Publication date: 2019-10-17
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
31508851
General Chemistry
Catalysis
Organic Chemistry
Abstract
A novel one‐pot cascade method for the assembly of valuable NO‐donor azasydnone scaffold has been developed. The 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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Total citations:
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Citations from 2024:
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(26%)
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GOST
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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.
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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.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/chem.201903526
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.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
PB - Wiley
SP - 14284-14289
IS - 63
VL - 25
PMID - 31508851
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
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@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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201903526},
number = {63},
pages = {14284--14289},
doi = {10.1002/chem.201903526}
}
Cite this
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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201903526.