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Issue 9, 2018
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An efficient approach to 4-chloro quinolines via TMSCl-mediated cascade cyclization of ortho-propynol phenyl azides

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Abstract

A novel and efficient strategy for the synthesis of 4-chloro quinolines via the TMSCl-mediated cascade cyclization of easily prepared ortho-propynol phenyl azides is developed. This reaction proceeds smoothly in moderate to excellent yields with a wide range of substrate compatibility. TMSCl acted not only as a promoter, but also as a chloro source in this transformation. Moreover, the obtained 4-chloro quinolines could be further derivated in an array of palladium-catalyzed coupling and nucleophilic substitution reactions to construct potential biologically active and pharmaceutical molecules.

Graphical abstract: An efficient approach to 4-chloro quinolines via TMSCl-mediated cascade cyclization of ortho-propynol phenyl azides

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Article information


Submitted
10 Feb 2018
Accepted
21 Mar 2018
First published
21 Mar 2018

Org. Chem. Front., 2018,5, 1537-1541
Article type
Research Article

An efficient approach to 4-chloro quinolines via TMSCl-mediated cascade cyclization of ortho-propynol phenyl azides

X. Song, R. Li, H. Ding, X. Chen, T. Yang, J. Bai, Q. Xiao and Y. Liang, Org. Chem. Front., 2018, 5, 1537
DOI: 10.1039/C8QO00162F

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