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. 2021 Sep 29;11(50):31152-31158.
doi: 10.1039/d1ra06330h. eCollection 2021 Sep 21.

A simple and efficient copper-catalyzed three-component reaction to synthesize (Z)-1,2-dihydro-2-iminoquinolines

Xiai Luo  1   2   3 , Yu Zhao  1 , Susu Tao  1 , Zhong-Tao Yang  1   2 , Hui Luo  1   2   4 , Weiguang Yang  1   2   4
Affiliations

A simple and efficient copper-catalyzed three-component reaction to synthesize (Z)-1,2-dihydro-2-iminoquinolines

Xiai Luo et al. RSC Adv. .

Abstract

A operationally simple synthesis of (Z)-1,2-dihydro-2-iminoquinolines that proceeds under mild conditions is achieved by copper-catalyzed reaction of 1-(2-aminophenyl)ethan-1-ones, sulfonyl azides and terminal ynones. In particular, the reaction goes through a base-free CuAAC/ring-opening process to obtain the Z-configured products due to hydrogen bonding.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of 2-iminoquinolines.
Fig. 1
Fig. 1. Single-crystal X-ray analysis of 4a (CCDC 2092343) and 4s (CCDC 2092351).
Fig. 2
Fig. 2. Single-crystal X-ray analysis of 4w (CCDC 2092350).
Scheme 2
Scheme 2. Hydrolysis of 2-iminoquinolines.
Scheme 3
Scheme 3. Plausible reaction mechanism.
See this image and copyright information in PMC

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