An Efficient Route to Tetrahydroindeno[2,1-b]pyrroles via a Base-Promoted Reaction of (E)-2-Alkynylphenylchalcone with 2-Isocyanoacetate

被引：50

作者：

Zheng, Danqing ^{[1
]}

Li, Shaoyu ^{[1
]}

Luo, Yong ^{[1
]}

Wu, Jie ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 24期

基金：

中国国家自然科学基金;

关键词：

DIVERSITY-ORIENTED SYNTHESIS; ORGANIC-SYNTHESIS; CASCADE REACTIONS; MULTICOMPONENT REACTIONS; DOMINO REACTIONS; TANDEM REACTION; CHEMISTRY; CYCLIZATIONS; HETEROCYCLES; ISOCYANIDES;

D O I：

10.1021/ol202708f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A base-promoted cascade reaction of (E)-2-alkynylphenylchalcone with 2-isocyanoacetate provides a novel and efficient route for the synthesis of tetrahydroindeno[2,1-b]pyrroles. The reaction proceeds smoothly in air under mild conditions with high efficiency.

引用

页码：6402 / 6405

页数：4

共 48 条

[1]

Arya P, 2001, ANGEW CHEM INT EDIT, V40, P339, DOI 10.1002/1521-3773(20010119)40:2<339::AID-ANIE339>3.0.CO

[2]

2-J

[3] A planning strategy for diversity-oriented synthesis [J].

Burke, MD ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58

[4] Diversity-oriented approach to 1,2-dihydroisoquinolin-3(4H)-imines via copper(I)-catalyzed reaction of (E)-2-ethynylphenylchalcone, sulfonyl azide and amine [J].

Chen, Zhiyuan ;

Ye, Chao ;

Gao, Liang ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2011, 47 (19) :5623-5625

[5] Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries [J].

Cordier, Christopher ;

Morton, Daniel ;

Murrison, Sarah ;

Nelson, Adam ;

O'Leary-Steele, Catherine .

NATURAL PRODUCT REPORTS, 2008, 25 (04) :719-737

[6] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[7]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[8]

2-U

[9] Asymmetric organocatalytic domino reactions [J].

Enders, Dieter ;

Grondal, Christoph ;

Huettl, Matthias R. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581

[10] An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes [J].

Feng, Jian-Jun ;

Zhang, Junliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7304-7307

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