Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
Publication type: Journal Article
Publication date: 2015-04-30
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
25927965
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.
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109
Total citations:
109
Citations from 2024:
14
(12.84%)
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GOST
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Miura T. et al. Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters // Organic Letters. 2015. Vol. 17. No. 10. pp. 2454-2457.
GOST all authors (up to 50)
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Miura T., Funakoshi Y., Fujimoto Y., Nakahashi J., MURAKAMI M. Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters // Organic Letters. 2015. Vol. 17. No. 10. pp. 2454-2457.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.5b00960
UR - https://doi.org/10.1021/acs.orglett.5b00960
TI - Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
T2 - Organic Letters
AU - Miura, Tomoya
AU - Funakoshi, Yuuta
AU - Fujimoto, Yoshikazu
AU - Nakahashi, Junki
AU - MURAKAMI, MASAHIRO
PY - 2015
DA - 2015/04/30
PB - American Chemical Society (ACS)
SP - 2454-2457
IS - 10
VL - 17
PMID - 25927965
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Miura,
author = {Tomoya Miura and Yuuta Funakoshi and Yoshikazu Fujimoto and Junki Nakahashi and MASAHIRO MURAKAMI},
title = {Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.orglett.5b00960},
number = {10},
pages = {2454--2457},
doi = {10.1021/acs.orglett.5b00960}
}
Cite this
MLA
Copy
Miura, Tomoya, et al. “Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters.” Organic Letters, vol. 17, no. 10, Apr. 2015, pp. 2454-2457. https://doi.org/10.1021/acs.orglett.5b00960.