Home / Publications / Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block

Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block

Yong Zhang 1
Yong Zhang
, 
Junxue Bai 2
Junxue Bai
, 
Song Sun 2
Song Sun
1 Suzhou Industrial Park Institute of Services and Outsourcing, Suzhou, Jiangsu, China
2 School of Petrochemical Engineering, Changzhou University, Changzhou, China
10.1016/j.mencom.2024.04.028
Published 2024-04-22
Communication , Volume 34, Issue 3, 401-403
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Zhang Y., Bai J., Sun S. Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block // Mendeleev Communications. 2024. Vol. 34. No. 3. pp. 401-403.
GOST all authors (up to 50) Copy
Zhang Y., Bai J., Sun S. Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block // Mendeleev Communications. 2024. Vol. 34. No. 3. pp. 401-403.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.04.028
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.028
TI - Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block
T2 - Mendeleev Communications
AU - Zhang, Yong
AU - Bai, Junxue
AU - Sun, Song
PY - 2024
DA - 2024/04/22
PB - Mendeleev Communications
SP - 401-403
IS - 3
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Zhang,
author = {Yong Zhang and Junxue Bai and Song Sun},
title = {Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.028},
number = {3},
pages = {401--403},
doi = {10.1016/j.mencom.2024.04.028}
}
MLA
Cite this
MLA Copy
Zhang, Yong, et al. “Copper(ii)-catalyzed three-component coupling sequence for the efficient synthesis of 2-arylquinolines: 1,4-dioxane serving as the C2 building block.” Mendeleev Communications, vol. 34, no. 3, Apr. 2024, pp. 401-403. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.028.

Keywords

1
4-dioxane
C2 building block
copper catalysis
cycloaddition
quinolines.
three-component coupling reaction

Abstract

A copper-catalyzed three-component coupling sequence for 2-arylquinolines formation from aromatic aldehydes, anilines and 1,4-dioxane has been described. Unexpectedly, 1,4-dioxane served as a C2 building block in this transformation. This formal [4 + 2] approach provides rapid access to 2-arylquinolines with broad substrate scope under mild conditions.

References

.
Synthesis and Biological Evaluation of Quinoline Salicylic Acids As P-Selectin Antagonists
Kaila N., Janz K., DeBernardo S., Bedard P.W., Camphausen R.T., Tam S., Tsao D.H., Keith J.C., Nickerson-Nutter C., Shilling A., Young-Sciame R., Wang Q.
Journal of Medicinal Chemistry, 2006
.
Quinoline, quinazoline and acridonealkaloids
Michael J.P.
Natural Product Reports, 2008
.
A review on anticancer potential of bioactive heterocycle quinoline
Afzal O., Kumar S., Haider M.R., Ali M.R., Kumar R., Jaggi M., Bawa S.
European Journal of Medicinal Chemistry, 2015
.
One-Step Catalytic Synthesis of Alkyl-Substituted Quinolines
Meyet C.E., Larsen C.H.
Journal of Organic Chemistry, 2014
.
Cu(ii)-promoted three-component coupling sequence for the efficient synthesis of substituted quinolines
Xiao F., Chen W., Liao Y., Deng G.
Organic and Biomolecular Chemistry, 2012
.
I2-Catalyzed oxidative dehydrogenative tandem cyclization of 2-methylquinolines, arylamines and 1,4-dioxane
Qi H., Yan Y., Liao Y., Jiang F., Gao H., Deng G.
Organic Chemistry Frontiers, 2021
.
Kalugin V.E., Adaeva O.I., Demchuk D.V., Semenov V.V.
Mendeleev Communications, 2023