Condition‐Based Selective Synthesis of 3,4,5‐Trisubstituted Isoxazoline N‐oxides, 4,5‐Dihydroisoxazoles and Isoxazoles

Functionalized isoxazoline N‐oxides, 4,5‐dihydroisoxazoles and isoxazoles have attracted considerable attention because of their wide applications. Starting from 1,1‐dimethoxy‐2‐nitroethene and aldehydes, a cascade approach to these heterocycles was explored to achieve structural diversity controlle...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2018-06, Vol.3 (23), p.6344-6348
Main Authors: Chen, Xinfei, Peng, Yanqing, Yu, Weiwei, Zhang, Xiao, Shao, Xusheng, Xu, Xiaoyong, Li, Zhong
Format: Article
Language:English
Subjects:
1,1-dimeoxyth-2-nitroethene
chemical selectivity
isoxazole derivatives
reaction conditions
structural diversity
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Summary:Functionalized isoxazoline N‐oxides, 4,5‐dihydroisoxazoles and isoxazoles have attracted considerable attention because of their wide applications. Starting from 1,1‐dimethoxy‐2‐nitroethene and aldehydes, a cascade approach to these heterocycles was explored to achieve structural diversity controlled by different reaction conditions. Furthermore, this new protocol provided a direct access to 4‐substituted‐3,5‐bis(methoxycarbonyl)‐4,5‐dihydroisoxazoles from aromatic aldehydes for the first time. A novel, concise, general and condition‐based cascade approach to the selective preparations of structurally diverse isoxazole derivatives, 3,4,5‐trisubstituted isoxazoline N‐oxides, 4,5‐dihydroisoxazoles or isoxazoles was presented. This new protocol provided a direct access to 4‐substituted‐3,5‐bis(methoxycarbonyl)‐4,5‐dihydroisoxazoles from aromatic aldehydes for the first time.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201800839