I2‐Promoted Synthesis of N‐Heteroaromatic Benzothiazoles and 2,2’‐Biquinolines via Deaminative Cyclization of Tertiary Amines
Publication type: Journal Article
Publication date: 2025-01-28
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
Abstract
A straightforward I2‐promoted Povarov multicomponent reaction strategy for the synthesis of N‐heteroaromatic benzothiazoles and 2, 2′‐biquinolines was described. This methodology involved a one‐pot two‐step procedure, tandem iodination/Kornblum oxidation, and [4+2] condensation. This protocol was characterized by broad scope of substrates (49 examples, 31–80 % yields), applicable for large‐scale preparation, and downstream derivatization of the products. Photophysical property of the two classes of bisheteroaryl compounds was investigated. Based on the rotatable C−C bond, 2‐(6‐methylquinolin‐2‐yl)benzo[d]thiazole (4 a) was successfully developed as a viscosity probe, which opened up new hopes and prospects for biomedical applications.
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Lv X. et al. I2‐Promoted Synthesis of N‐Heteroaromatic Benzothiazoles and 2,2’‐Biquinolines via Deaminative Cyclization of Tertiary Amines // Chemistry - A European Journal. 2025. Vol. 31. No. 12. e202404614
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Lv X., Zhang J., Gao X., Xu Z., Hu Z., Jia Q., Li S., Ma C. I2‐Promoted Synthesis of N‐Heteroaromatic Benzothiazoles and 2,2’‐Biquinolines via Deaminative Cyclization of Tertiary Amines // Chemistry - A European Journal. 2025. Vol. 31. No. 12. e202404614
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TY - JOUR
DO - 10.1002/chem.202404614
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404614
TI - I2‐Promoted Synthesis of N‐Heteroaromatic Benzothiazoles and 2,2’‐Biquinolines via Deaminative Cyclization of Tertiary Amines
T2 - Chemistry - A European Journal
AU - Lv, Xueyan
AU - Zhang, Jiachen
AU - Gao, Xiaoyang
AU - Xu, Zhiming
AU - Hu, Zongrui
AU - Jia, Qingbo
AU - Li, Shichen
AU - Ma, Chen
PY - 2025
DA - 2025/01/28
PB - Wiley
IS - 12
VL - 31
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2025_Lv,
author = {Xueyan Lv and Jiachen Zhang and Xiaoyang Gao and Zhiming Xu and Zongrui Hu and Qingbo Jia and Shichen Li and Chen Ma},
title = {I2‐Promoted Synthesis of N‐Heteroaromatic Benzothiazoles and 2,2’‐Biquinolines via Deaminative Cyclization of Tertiary Amines},
journal = {Chemistry - A European Journal},
year = {2025},
volume = {31},
publisher = {Wiley},
month = {jan},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404614},
number = {12},
pages = {e202404614},
doi = {10.1002/chem.202404614}
}