Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines
Publication type: Journal Article
Publication date: 2023-09-22
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
37738046
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.
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Total citations:
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Citations from 2024:
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(83.34%)
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GOST
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Agafonova A. V. et al. Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines // Organic Letters. 2023. Vol. 25. No. 39. pp. 7165-7169.
GOST all authors (up to 50)
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Agafonova A. V., Golubev A. A., Smetanin I. A., Khlebnikov A. F., Spiridonova D. V., Novikov M. S. Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines // Organic Letters. 2023. Vol. 25. No. 39. pp. 7165-7169.
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TY - JOUR
DO - 10.1021/acs.orglett.3c02696
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c02696
TI - Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines
T2 - Organic Letters
AU - Agafonova, Anastasiya V
AU - Golubev, Artem A
AU - Smetanin, Ilia A
AU - Khlebnikov, Alexander F
AU - Spiridonova, Darya V.
AU - Novikov, Mikhail S.
PY - 2023
DA - 2023/09/22
PB - American Chemical Society (ACS)
SP - 7165-7169
IS - 39
VL - 25
PMID - 37738046
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2023_Agafonova,
author = {Anastasiya V Agafonova and Artem A Golubev and Ilia A Smetanin and Alexander F Khlebnikov and Darya V. Spiridonova and Mikhail S. Novikov},
title = {Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c02696},
number = {39},
pages = {7165--7169},
doi = {10.1021/acs.orglett.3c02696}
}
Cite this
MLA
Copy
Agafonova, Anastasiya V., et al. “Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines.” Organic Letters, vol. 25, no. 39, Sep. 2023, pp. 7165-7169. https://pubs.acs.org/doi/10.1021/acs.orglett.3c02696.