Divergent Synthesis of Isoxazolo[5,4‐b]pyridines

Author:

Li Min123,Li Wenzhe123,Huang Min123,Zhang Xiaomei123ORCID

Affiliation:

1. Asymmetric Synthesis and Chiraltechnology Key Laboratory of Sichuan Province Chengdu Institute of Organic Chemistry Chinese Academy of Sciences Chengdu China

2. University of Chinese Academy of Sciences Beijing China

3. Department of Chemistry Xihua University Beijing China

Abstract

AbstractIsoxazolopyridines are highly significant for the development of pharmaceuticals and new materials. In continuation of our ongoing research on transformations of 5‐aminoisoxazoles, we report herein a divergent synthesis of two kinds of novel isoxazolo[5,4‐b] pyridines through condensation of 5‐aminoisoxazoles with β,γ‐alkynyl‐α‐imino esters. By using two different silver salts and a phosphoric acid as catalysts, isoxazolo[5,4‐b] pyridine‐α‐carboxylates and isoxazolo[5,4‐b] pyridine‐γ‐carboxylates were constructed as major isomers in moderate to good yields, respectively. The structures of the two kinds of the isoxazolo[5,4‐b] pyridines were confirmed by X‐ray crystal structural analysis. Furthermore, control experiments were conducted to elucidate the reaction mechanism.

Funder

Xihua University

Publisher

Wiley

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