Palladium-catalyzed C-C bond cleavage of N-cyclopropyl acylhydrazones

被引：1

作者：

Fujioka, Hiroki ^{[1
]}

Yasui, Motohiro ^{[1
]}

Hamada, Shohei ^{[2
]}

Fukumi, Kohei ^{[1
]}

Takeda, Norihiko ^{[1
]}

Kobayashi, Yusuke ^{[2
]}

Furuta, Takumi ^{[2
]}

Ueda, Masafumi ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe 6588558, Japan

[2] Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078414, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 16期

基金：

日本学术振兴会;

关键词：

MOLECULAR-OXYGEN; C(SP(3))-H BONDS; DIRECT ARYLATION; DIRECTING-GROUP; H ACTIVATION; HYDRAZONE; FUNCTIONALIZATIONS; INDOLIZATION; OXIDATION; STRATEGY;

D O I：

10.1039/d4ob00349g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Despite their utility as directing groups, the C-C bond cleavage of cyclopropanes utilizing hydrazones has not been explored. Herein, Pd-catalyzed C-C bond cleavage reaction of N-cyclopropyl acylhydrazones, followed by cycloisomerization to yield pyrazoles, has been developed. The protocol enables the synthesis of various alpha-pyrazole carbonyl compounds, which have a potential of biological activity. Control experiments and DFT calculations suggest that beta-carbon elimination of a stable 6-membered chelate palladium complex occurs, generating a conjugated azine as a reaction intermediate for the following cycloisomerization.

引用

页码：3262 / 3267

页数：6

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