Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of Isoxazoles and Pyrroles

Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of Isoxazoles and Pyrroles

Described is an iterative assembly of nitrile oxides and ynamides for the synthesis of isoxazoles and pyrroles. The nitrile oxides could undergo Cu­(I)-free cyclization with terminal ynamides for accessing isoxazoles, which could engage in another cyclization with internal ynamides in the presence o...

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Veröffentlicht in:Journal of organic chemistry 2019-09, Vol.84 (18), p.12157-12164
Hauptverfasser: Chen, Changwei, Cui, Sunliang
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container_title Journal of organic chemistry
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creator Chen, Changwei
Cui, Sunliang
description Described is an iterative assembly of nitrile oxides and ynamides for the synthesis of isoxazoles and pyrroles. The nitrile oxides could undergo Cu­(I)-free cyclization with terminal ynamides for accessing isoxazoles, which could engage in another cyclization with internal ynamides in the presence of Au­(I) catalyst to deliver pyrroles, and the reaction could be carried out in a two-step, one-pot procedure. This process is featured with mild reaction condition and broad substrate scope for the synthesis of heterocycles.
doi_str_mv 10.1021/acs.joc.9b01430
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title Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of Isoxazoles and Pyrroles
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