Substrate Controlled [3+3] Relay Catalytic Cyclization of α-(3-Isoindolinonyl) Propargylic Alcohols with 5-Aminoisoxazoles

被引：1
|
作者：
Li, Wenzhe [1 ,3 ]
Gao, Min [2 ]
Li, Min [1 ,3 ]
Yang, Shuang [2 ]
Zhang, Xiaomei [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
[2] Xihua Univ, Dept Chem, Chengdu, Peoples R China
[3] Univ Chinese Acad Sci, Beijing, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 06期
关键词：
relay catalysis; isoindolinones; 5-aminoisoxazoles; spiro-isoindolinone-dihydropyridines; isoxazolo [4,5-b]pyridines; SPIRO-ISOINDOLINONE-INDOLINES; ANNULATION; CYCLOADDITION; KETIMINES; SPIROANNULATION; SELECTIVITY; INHIBITORS; ALKYNES; IMINES; ACCESS;
D O I：
10.1002/ajoc.202400055
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two different skeletons have been constructed by cyclization of alpha-(3-isoindolinonyl) propargylic alcohols with 5-aminoisoxazoles bearing different N-substituents under the relay catalysis of Bronsted acid and Lewis acid. This method provided spiro-isoindolinone-dihydropyridines with moderate to high yields (up to 99 %) as well as isoxazolo[4,5-b]pyridines in moderate to good yields (up to 86 %). The structures of two products were determined by X-ray crystal structural analyses. Moreover, fluorescence testing proved that one of the isoxazolo[4,5-b]pyridines exhibited aggregation induced emission (AIE) effect. Finally, the control experiments revealed the possible reaction mechanism. Relay catalytic [3+3] cyclization of alpha-(3-isoindolinonyl) propargylic alcohols with 5-aminoisoxazoles bearing different N-substituents provide novel spiro-isoindolinone-dihydropyridines as well as isoxazolo[4,5-b]pyridines in moderate to good yields. The structures of two products are determined by X-ray crystal structural analyses. image
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页数：5
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