A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles
Publication type: Journal Article
Publication date: 2020-05-21
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32438811
Organic Chemistry
Abstract
An efficient direct approach to triazole-fused sultams has been developed. The key step of the proposed strategy is base-mediated cyclization of sulfonamide-tethered 5-iodo-1,2,3-triazoles which are readily available via an improved protocol for Cu-catalyzed 1,3-dipolar cycloaddition. The annulation of the sultam fragment to the triazole ring proceeds smoothly under transition metal-free conditions in the presence of Cs2CO3 in dioxane at 100 °C and affords fused heterocycles in high yields up to 99%. A favorability of SNAr-like mechanism for the cyclization was supported by DFT calculations. An applicability of the developed procedure to modification of natural compounds was demonstrated by a preparation of a bile acid derivative.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
|
|
|
Journal of Organic Chemistry
4 publications, 14.29%
|
|
|
Organic and Biomolecular Chemistry
4 publications, 14.29%
|
|
|
Russian Journal of Organic Chemistry
3 publications, 10.71%
|
|
|
Synthesis
2 publications, 7.14%
|
|
|
New Journal of Chemistry
2 publications, 7.14%
|
|
|
Журнал органической химии
2 publications, 7.14%
|
|
|
Beilstein Journal of Organic Chemistry
1 publication, 3.57%
|
|
|
Chemistry - A European Journal
1 publication, 3.57%
|
|
|
ChemistrySelect
1 publication, 3.57%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 3.57%
|
|
|
Journal of Heterocyclic Chemistry
1 publication, 3.57%
|
|
|
Organic Reaction Mechanisms
1 publication, 3.57%
|
|
|
Organic Letters
1 publication, 3.57%
|
|
|
European Journal of Organic Chemistry
1 publication, 3.57%
|
|
|
Journal of Macromolecular Science Part A
1 publication, 3.57%
|
|
|
1
2
3
4
|
Publishers
|
1
2
3
4
5
6
|
|
|
Royal Society of Chemistry (RSC)
6 publications, 21.43%
|
|
|
Wiley
6 publications, 21.43%
|
|
|
American Chemical Society (ACS)
5 publications, 17.86%
|
|
|
Pleiades Publishing
3 publications, 10.71%
|
|
|
Georg Thieme Verlag KG
2 publications, 7.14%
|
|
|
Elsevier
2 publications, 7.14%
|
|
|
Akademizdatcenter Nauka
2 publications, 7.14%
|
|
|
Beilstein-Institut
1 publication, 3.57%
|
|
|
Taylor & Francis
1 publication, 3.57%
|
|
|
1
2
3
4
5
6
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
28
Total citations:
28
Citations from 2024:
11
(39%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Tatevosyan S. S. et al. A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 12. pp. 7863-7876.
GOST all authors (up to 50)
Copy
Tatevosyan S. S., Kotovshchikov Y. N., Latyshev G. V., Erzunov D. A., Sokolova D. V., Beletskaya I. P., Lukashev N. V. A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 12. pp. 7863-7876.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.0c00520
UR - https://doi.org/10.1021/acs.joc.0c00520
TI - A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles
T2 - Journal of Organic Chemistry
AU - Tatevosyan, Stepan S
AU - Kotovshchikov, Yury N
AU - Latyshev, Gennadij V
AU - Erzunov, Dmitry A
AU - Sokolova, Darina V
AU - Beletskaya, Irina P.
AU - Lukashev, Nikolay V
PY - 2020
DA - 2020/05/21
PB - American Chemical Society (ACS)
SP - 7863-7876
IS - 12
VL - 85
PMID - 32438811
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Tatevosyan,
author = {Stepan S Tatevosyan and Yury N Kotovshchikov and Gennadij V Latyshev and Dmitry A Erzunov and Darina V Sokolova and Irina P. Beletskaya and Nikolay V Lukashev},
title = {A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.0c00520},
number = {12},
pages = {7863--7876},
doi = {10.1021/acs.joc.0c00520}
}
Cite this
MLA
Copy
Tatevosyan, Stepan S., et al. “A Route to Triazole-Fused Sultams via Metal-Free Base-Mediated Cyclization of Sulfonamide-Tethered 5-Iodotriazoles.” Journal of Organic Chemistry, vol. 85, no. 12, May. 2020, pp. 7863-7876. https://doi.org/10.1021/acs.joc.0c00520.