Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition

Arunan Palanimuthu; Chinpiao Chen; Gene-Hsian Lee

doi:10.1039/D0RA01264E

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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition†

Arunan Palanimuthu,

^b Chinpiao Chen

*^ab and Gene-Hsian Lee^c

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* Corresponding authors

^a Department of Nursing, Tzu Chi University of Science and Technology, Hualien 970, Taiwan
E-mail: chinpiao@ems.tcust.edu.tw
Fax: +886 3 856 1097
Tel: +886 3 857 2158 ext. 2624

^b Department of Chemistry, National Dong Hwa University, Soufeng, Hualien 974, Taiwan

^c Instrumentation Center, College of Science, National Taiwan University, Taipei 106, Taiwan

Abstract

A three-component cascade reaction involving 2-alkenyl aniline, aldehydes, and ethyl cyanoacetate in the presence of DBU to synthesize highly substituted 1,2,3,4-tetrahydroquinolines is reported. The reaction proceeded through the Knoevenagel condensation of ethyl cyanoacetate with aldehydes followed by the aza-Michael–Michael addition with 2-alkenyl anilines to prepare the tetrahydroquinoline scaffolds.

This article is part of the themed collection: 2020 RSC Advances HOT Article Collection

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DOI: https://doi.org/10.1039/D0RA01264E
Article type: Paper
Submitted: 10 Feb 2020
Accepted: 26 Mar 2020
First published: 03 Apr 2020
This article is Open Access

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RSC Adv., 2020,10, 13591-13600

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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition

A. Palanimuthu, C. Chen and G. Lee, RSC Adv., 2020, 10, 13591 DOI: 10.1039/D0RA01264E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition†

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Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition

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