Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates
Publication type: Journal Article
Publication date: 2020-06-08
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32508100
Organic Chemistry
Abstract
An efficient cascade approach to thiosubstituted benzoxazoles has been developed. The transformation starts with in situ generation of diazo compound via annulation-triggered electrocyclic opening of 1,2,3-triazole ring. The subsequent Cu-catalyzed trapping of diazo intermediates by various thiols affords desired heterocycles in generally good yields up to 91%. The protocol features very good functional group tolerance and is applicable to substrates with different electronic properties.
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24
Total citations:
24
Citations from 2024:
10
(41.66%)
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MLA
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GOST
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Kotovshchikov Y. N. et al. Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9015-9028.
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Kotovshchikov Y. N., Latyshev G. V., Kirillova E. A., Moskalenko U. D., Lukashev N. V., Beletskaya I. P. Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 9015-9028.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.0c00931
UR - https://doi.org/10.1021/acs.joc.0c00931
TI - Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates
T2 - Journal of Organic Chemistry
AU - Kotovshchikov, Yury N
AU - Latyshev, Gennadij V
AU - Kirillova, Elena A
AU - Moskalenko, Uliana D
AU - Lukashev, Nikolay V
AU - Beletskaya, Irina P.
PY - 2020
DA - 2020/06/08
PB - American Chemical Society (ACS)
SP - 9015-9028
IS - 14
VL - 85
PMID - 32508100
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Kotovshchikov,
author = {Yury N Kotovshchikov and Gennadij V Latyshev and Elena A Kirillova and Uliana D Moskalenko and Nikolay V Lukashev and Irina P. Beletskaya},
title = {Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.0c00931},
number = {14},
pages = {9015--9028},
doi = {10.1021/acs.joc.0c00931}
}
Cite this
MLA
Copy
Kotovshchikov, Yury N., et al. “Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates.” Journal of Organic Chemistry, vol. 85, no. 14, Jun. 2020, pp. 9015-9028. https://doi.org/10.1021/acs.joc.0c00931.