Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the ring contraction and deformylative functionalization of piperidine derivatives

被引：26

作者：

Wang, Fang ^{[1
]}

Zhang, Xinying ^{[1
]}

He, Yan ^{[1
]}

Fan, Xuesen ^{[1
]}

机构：

[1] Henan Normal Univ, Henan Key Lab Organ Funct Mol & Drug Innovat,Sch, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Key Lab Green Chem Media & React,Minist Educ,Sch, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CATALYZED OXIDATIVE CYCLIZATION; INACTIVATED CYCLIC AMINES; GAMMA-LACTAMS; C-O; ROUTE; ACIDS; CLEAVAGE; AMIDES; FACILE; MILD;

D O I：

10.1039/c8ob02640h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using a specific oxidant and additive.

引用

页码：156 / 164

页数：9

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