A Rapid Method to Aromatic Aminoalkyl Esters via the Catalyst-Free Difunctionalization of C–N Bonds

Qiming Zhu; Peng Yang; Mingwei Chen; Jinyu Hu; Luyi Yang

doi:10.1055/s-0036-1591577

Synthesis, Table of Contents

Synthesis 2018; 50(13): 2587-2594
DOI: 10.1055/s-0036-1591577

paper

A Rapid Method to Aromatic Aminoalkyl Esters via the Catalyst-Free Difunctionalization of C–N Bonds

Authors

Qiming Zhu*

^aKey Laboratory of Natural Active Pharmaceutical Constituents of Jiang Xi Province, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. of China Email: qmzhu@jxycu.edu.cn
Peng Yang

^aKey Laboratory of Natural Active Pharmaceutical Constituents of Jiang Xi Province, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. of China Email: qmzhu@jxycu.edu.cn
Mingwei Chen

^aKey Laboratory of Natural Active Pharmaceutical Constituents of Jiang Xi Province, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. of China Email: qmzhu@jxycu.edu.cn

^bInstitute of Engineering Research, Jiangxi University of Science and Technology, Ganzhou 341000, P. R. of China
Jinyu Hu

^aKey Laboratory of Natural Active Pharmaceutical Constituents of Jiang Xi Province, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. of China Email: qmzhu@jxycu.edu.cn
Luyi Yang

^aKey Laboratory of Natural Active Pharmaceutical Constituents of Jiang Xi Province, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. of China Email: qmzhu@jxycu.edu.cn

Abstract

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Abstract

A novel multicomponent reaction involving a direct C–N esterification/arylation has been developed. This catalyst-free process was conducted with cyclic tertiary amines via a facile C–N cleavage to provide the alkyl group and nitrogen source. The operationally simple method to rapidly combine cyclic tertiary amines, haloazaarenes and carboxylic acids (or anhydrides) affords an efficient access to aromatic aminoalkyl esters, potential drug-like products, in good to excellent yields.

Key words

multicomponent reaction - C–N cleavage - esterification - arylation - catalyst free

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References

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Supplementary Material

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