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Molecules 2019, 24(5), 988; https://doi.org/10.3390/molecules24050988

Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water

1
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu 610052, China
2
School of Biological Science and Technology, University of Jinan, Jinan 250022, China
3
State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medical, Chinese Academy of Sciences, Shanghai 201203, China
4
University of Chinese Academy of Sciences, Beijing 100049, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Gianfranco Favi
Received: 4 February 2019 / Revised: 1 March 2019 / Accepted: 4 March 2019 / Published: 11 March 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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Abstract

The present study describes an AuPPh3Cl/AgSbF6-catalyzed cascade reaction between amine nucleophiles and alkynoic acids in water. This process proceeds in high step economy with water as the sole coproduct, and leads to the generation of two rings, together with the formation of three new bonds in a single operation. This green cascade process exhibits valuable features such as low catalyst loading, good to excellent yields, high efficiency in bond formation, excellent selectivity, great tolerance of functional groups, and extraordinarily broad substrate scope. In addition, this is the first example of the generation of an indole/thiophene/pyrrole/pyridine/naphthalene/benzene-fused N-heterocycle library through gold catalysis in water from readily available materials. Notably, the discovery of antibacterial molecules from this library demonstrates its high quality and potential for the identification of active pharmaceutical ingredients. View Full-Text
Keywords: amine nucleophiles; alkynoic acids; cascade reaction; gold catalysis; fused N-heterocycles amine nucleophiles; alkynoic acids; cascade reaction; gold catalysis; fused N-heterocycles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Jia, X.; Li, P.; Liu, X.; Lin, J.; Chu, Y.; Yu, J.; Wang, J.; Liu, H.; Zhao, F. Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water. Molecules 2019, 24, 988.

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