Transition-Metal-Free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds

被引：66

作者：

Yao, Qiyi ^{[1
]}

Kong, Lingkai ^{[1
]}

Wang, Mengdan ^{[1
]}

Yuan, Yang ^{[1
]}

Sun, Ruizhuo ^{[1
]}

Li, Yanzhong ^{[1
]}

机构：

[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 500 Dongchuan Rd, Shanghai 200241, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 07期

基金：

中国国家自然科学基金;

关键词：

CARBON SIGMA-BONDS; PROMOTED TANDEM REACTION; C-C CLEAVAGE; CHROMONE DERIVATIVES; ARYNE INSERTION; CATALYZED SYNTHESIS; BETA-KETOESTERS; SINGLE-BOND; ALKYNES; ACTIVATION;

D O I：

10.1021/acs.orglett.8b00206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds through C-C sigma-bond activation. Notable features of the procedure indude easily accessible starting materials, good functional group tolerance, and high atom economy.

引用

收藏

页码：1744 / 1747

页数：4

相关论文

共 39 条

[1] THE OXIDATION PRODUCTS OF PHENOLS .1. THE STRUCTURE OF PURPUROGALLIN [J].

BARLTROP, JA ;

NICHOLSON, JS .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (FEB) :116-120

[2] Base-Promoted Tandem Reaction Involving Insertion into Carbon-Carbon σ-Bonds: Synthesis of Xanthone and Chromone Derivatives [J].

Cheng, Xingcan ;

Zhou, Yuanyuan ;

Zhang, Fangfang ;

Zhu, Kai ;

Liu, Yuanyuan ;

Li, Yanzhong .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (36) :12655-12659

[3] Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems [J].

Dermenci, Alpay ;

Coe, Jotham W. ;

Dong, Guangbin .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05) :567-581

[4]

Dong G., 2014, TOP CURR CHEM, V346

[5] Cyclohexyne Cycloinsertion by an Annulative Ring Expansion Cascade [J].

Gampe, Christian M. ;

Boulos, Samy ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (24) :4092-4095

[6]

Gill M, 1987, Fortschr Chem Org Naturst, V51, P1

[7] Nickel/Lewis Acid-Catalyzed Cyanoesterification and Cyanocarbamoylation of Alkynes [J].

Hirata, Yasuhiro ;

Yada, Akira ;

Morita, Eiji ;

Nakao, Yoshiaki ;

Hiyama, Tamejiro ;

Ohashi, Masato ;

Ogoshi, Sensuke .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (29) :10070-10077

[8] Cyanoesterification of 1,2-Dienes Catalyzed by Nickel [J].

Hirata, Yasuhiro ;

Inui, Tomohiko ;

Nakao, Yoshiaki ;

Hiyama, Tamejiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) :6624-6631

[9] RING-CLOSURE REACTIONS OF BIFUNCTIONAL CHAIN MOLECULES [J].

ILLUMINATI, G ;

MANDOLINI, L .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (04) :95-102

[10] Nickel-Catalyzed Chemo-, Regio- and Diastereoselective Bond Formation through Proximal C-C Cleavage of Benzocyclobutenones [J].

Julia-Hernandez, Francisco ;

Ziadi, Asraa ;

Nishimura, Akira ;

Martin, Ruben .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) :9537-9541

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