Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

被引:13
|
作者
Li, Na [1 ]
Hu, Bing [1 ]
Zhang, Xinying [1 ]
Fan, Xuesen [1 ]
机构
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine C, NMPA Key Lab Res & Evaluat Innovat Drug, Key Lab Green Chem & Media React,Minist Educ,Sch C, Xinxiang 453007, Henan, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
基金
中国国家自然科学基金;
关键词
3+2 CYCLOADDITION; FACILE ACCESS; 2-ARYLINDOLES; ANNULATION; CINNOLINES;
D O I
10.1021/acs.joc.2c01756
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Presented herein is a controllable selective construction of spiro or fused heterocyclic scaffolds through the onepot cascade reactions of 1-phenylpyrazolidinones with maleimides. To be specific, succinimide spiro pyrazolo[1,2-a]pyrazolones were effectively formed via [4 + 1] spiroannulation of 1-phenylpyrazolidinones with maleimides through simultaneous C(sp(2))-H bond activation/functionalization and intramolecular cyclization along with the traceless fusion of the pyrazolidinonyl unit into the final product. In this reaction, air acts as a cost-effective and environmentally sustainable oxidant to assist the regeneration of the Rh(III) catalyst. Alternatively, succinimide-fused pyrazolidinonylcinnolines were formed from the same starting materials through an initial [4 + 1] spiroannulation followed by basepromoted skeleton rearrangement of the in situ formed spiro product without isolation. Notable features of these protocols include easily tunable selectivity, broad substrate scope, cost-effective and sustainable oxidant, excellent atom economy, and facile scalability.
引用
收藏
页码:60 / 74
页数:15
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