(3+2) Cycloaddition Reaction of the Endocyclic N-Silyl Enamine and N,N′-Cyclic Azomethine Imine

被引：12

作者：

Cao, Vinh Do ^{[1
]}

Kim, Huiae ^{[1
]}

Kwak, Jaesung ^{[2
]}

Joung, Seewon ^{[1
,3
]}

机构：

[1] Mokpo Natl Univ, Dept Chem, Muan 58554, Jeonnam, South Korea

[2] Korea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Daejeon 34114, South Korea

[3] Inha Univ, Dept Chem, Incheon 22212, South Korea

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

1,3-DIPOLAR CYCLOADDITIONS; COMPLEXITY; ALDEHYDES; DEAROMATIZATION; QUINOLINES; REDUCTION; DIENAMINE; PYRIDINES;

D O I：

10.1021/acs.orglett.2c00366

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the (3 + 2) cycloaddition reaction of endocyclic N-silyl enamines and N,N'-cyclic azomethine imines. This process utilized the versatile endocyclic N-silyl enamine intermediates from the dearomative hydrosilylation of N-heteroarenes. The resulting tetracyclic pyrazolidinone structure was synthesized by a straightforward and atom-economical process. We also discussed the plausible origins of the different reactivity and endo/exo selectivity in terms of the structures of each proposed transition state. The successful gram-scale synthesis demonstrated the synthetic utility.

引用

页码：1974 / 1978

页数：5

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