Organic Letters, volume 23, issue 16, pages 6362-6366
Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives
Publication type: Journal Article
Publication date: 2021-08-12
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. The reaction with primary alcohols and phenols gives alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Thiophenols react with 2H-azirine-2-carbonyl azides to afford S-aryl 2-(1H-tetrazol-1-yl)ethanethioates. The mechanism of the nucleophile-induced rearrangement of 2H-azirine-2-carbonyl azides is discussed on the basis of DFT calculations as well as kinetic and 15N labeling experiments.
Citations by journals
|
1
2
|
|
|
Progress in Heterocyclic Chemistry
|
Progress in Heterocyclic Chemistry
2 publications, 33.33%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
1 publication, 16.67%
|
|
Molecules
|
Molecules
1 publication, 16.67%
|
|
Russian Journal of General Chemistry
|
Russian Journal of General Chemistry
1 publication, 16.67%
|
|
European Journal of Organic Chemistry
|
European Journal of Organic Chemistry
1 publication, 16.67%
|
|
1
2
|
Citations by publishers
|
1
2
|
|
|
Elsevier
|
Elsevier
2 publications, 33.33%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
1 publication, 16.67%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 16.67%
|
|
Pleiades Publishing
|
Pleiades Publishing
1 publication, 16.67%
|
|
Wiley
|
Wiley
1 publication, 16.67%
|
|
1
2
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2022,2023,2024],"ids":[0,0,0],"codes":[0,0,0],"imageUrls":["","",""],"datasets":[{"label":"Citations number","data":[3,2,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":["50","33.33","16.67"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Progress in Heterocyclic Chemistry","Organic and Biomolecular Chemistry","Molecules","Russian Journal of General Chemistry","European Journal of Organic Chemistry"],"ids":[17224,541,1770,13581,19472],"codes":[0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,16.67,16.67,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Elsevier","Royal Society of Chemistry (RSC)","Multidisciplinary Digital Publishing Institute (MDPI)","Pleiades Publishing","Wiley"],"ids":[17,123,202,101,11],"codes":[0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,16.67,16.67,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Efimenko N. I. et al. Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives // Organic Letters. 2021. Vol. 23. No. 16. pp. 6362-6366.
GOST all authors (up to 50)
Copy
Efimenko N. I., Tomashenko O. A., Spiridonova D. V., Novikov M. S., Khlebnikov A. F. Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives // Organic Letters. 2021. Vol. 23. No. 16. pp. 6362-6366.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.1c02157
UR - https://doi.org/10.1021%2Facs.orglett.1c02157
TI - Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives
T2 - Organic Letters
AU - Efimenko, Nikita I
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Tomashenko, Olesya A
AU - Spiridonova, Darya V.
PY - 2021
DA - 2021/08/12 00:00:00
PB - American Chemical Society (ACS)
SP - 6362-6366
IS - 16
VL - 23
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex
Copy
@article{2021_Efimenko,
author = {Nikita I Efimenko and Mikhail S. Novikov and Alexander F Khlebnikov and Olesya A Tomashenko and Darya V. Spiridonova},
title = {Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Facs.orglett.1c02157},
number = {16},
pages = {6362--6366},
doi = {10.1021/acs.orglett.1c02157}
}
Cite this
MLA
Copy
Efimenko, Nikita I., et al. “Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives.” Organic Letters, vol. 23, no. 16, Aug. 2021, pp. 6362-6366. https://doi.org/10.1021%2Facs.orglett.1c02157.