Robust Organocatalytic Three-Component Approach to 1,3-Diarylallylidene Pyrazolones via Consecutive Double Condensation Reactions

被引:0
|
作者
Patel, Ashvani K. [1 ]
Samanta, Sampak [1 ]
机构
[1] Indian Inst Technol Indore, Dept Chem, Simrol 453552, Madhya Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期
关键词
STEREOSELECTIVE-SYNTHESIS; UNSATURATED PYRAZOLONES; ALLYLIC ALKYLATION; DERIVATIVES; SPIROOXINDOLES; INHIBITORS; CHEMISTRY; OXINDOLES; SEQUENCE; CASCADE;
D O I
10.1021/acs.joc.4c02273
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A robust pyrrolidine-BzOH salt-catalyzed one-pot three-component reaction involving 4-unsubstituted pyrazolones, aryl/heteroarylaldehydes, and aryl methyl ketones is reported for the first time. This catalytic process fortifies an efficient method, allowing for the practical synthesis of a wide array of synthetically useful 1,3-diarylallylidene pyrazolones in good to high yields exclusively in their single geometrical isomer forms. Furthermore, this catalyst facilitates a sequential double condensation reaction under thermal conditions, thereby enabling two consecutive C=C bonds through displacement of aryl groups. Moreover, this organocatalytic technique achieves a 100% carbon atom economy, marking a significant step forward toward efficient and sustainable synthesis.
引用
收藏
页码:17528 / 17543
页数:16
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