Tetrahedron Letters, volume 59, issue 4, pages 372-374

Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides

Publication typeJournal Article
Publication date2018-01-01
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor1.8
ISSN00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A library of 4′-chloro- and 4′-fluorosulfonyl-substituted chalcones was prepared via the aldol-type condensation reactions of 4-acetylbenzene-1-sulfonyl halides with various aromatic aldehydes, either in absolute ethanol or glacial acetic acid, in the presence of dry HCl. This represents the first examples of chalcone sulfonyl halides in which the phenone ring bears one of these functional groups. The reactivity of the chalcone sulfonyl halides were strongly dependent on the styrene ring substituents; sulfonyl chlorides reacted with most nucleophiles (e.g. amines, alcohols), while sulfonyl fluorides reacted only with charged nucleophiles (e.g. phenolates).

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GOST Copy
Semenok D. V. et al. Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides // Tetrahedron Letters. 2018. Vol. 59. No. 4. pp. 372-374.
GOST all authors (up to 50) Copy
Semenok D. V., Kletskov A. V., Dikusar E., I. Potkin V., Lukin O. Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides // Tetrahedron Letters. 2018. Vol. 59. No. 4. pp. 372-374.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.tetlet.2017.12.044
UR - https://doi.org/10.1016%2Fj.tetlet.2017.12.044
TI - Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides
T2 - Tetrahedron Letters
AU - Semenok, Dmitry V.
AU - Kletskov, Alexey V
AU - Dikusar, Evgenij
AU - I. Potkin, Vladimir
AU - Lukin, Oleg
PY - 2018
DA - 2018/01/01 00:00:00
PB - Elsevier
SP - 372-374
IS - 4
VL - 59
SN - 0040-4039
SN - 1873-3581
ER -
BibTex |
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BibTex Copy
@article{2018_Semenok,
author = {Dmitry V. Semenok and Alexey V Kletskov and Evgenij Dikusar and Vladimir I. Potkin and Oleg Lukin},
title = {Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides},
journal = {Tetrahedron Letters},
year = {2018},
volume = {59},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016%2Fj.tetlet.2017.12.044},
number = {4},
pages = {372--374},
doi = {10.1016/j.tetlet.2017.12.044}
}
MLA
Cite this
MLA Copy
Semenok, Dmitry V., et al. “Efficient synthesis of chalcone-4′-sulfonyl chlorides and fluorides.” Tetrahedron Letters, vol. 59, no. 4, Jan. 2018, pp. 372-374. https://doi.org/10.1016%2Fj.tetlet.2017.12.044.
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