Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

被引：3

作者：

Li, Yong ^{[1
,2
]}

Huang, Zheng ^{[1
]}

Xu, Jia ^{[1
]}

Ding, Yong ^{[1
]}

Tang, Ding-Yong ^{[1
]}

Lei, Jie ^{[1
,2
]}

Li, Hong-yu ^{[2
]}

Chen, Zhong-Zhu ^{[1
]}

Xu, Zhi-Gang ^{[1
]}

机构：

[1] Chongqing Univ Arts & Sci, Coll Pharm, Natl & Local Joint Engn Res Ctr Targeted & Innova, Chongqing Key Lab Kinase Modulators Innovat Med, Chongqing 402160, Peoples R China

[2] Univ Arkansas Med Sci, Coll Pharm, Dept Pharmaceut Sci, Little Rock, AR 72205 USA

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

关键词：

Dieckmann cyclization; multicomponent reactions; nitrogen heterocycles; one-pot reaction; Ugi reaction; MULTICOMPONENT REACTIONS; ISOCYANIDE; ELUCIDATION; CHEMISTRY; PRODUCTS; STRATEGY;

D O I：

10.3762/bjoc.16.63

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods.

引用

页码：663 / 669

页数：7

共 45 条

[1]

[Anonymous], 1962, ANGEW CHEM INT ED EN, V1, P8

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

Burke, MD ;

Schreiber, SL .

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

[3]

Chen Z., 2017, Chin. Patent, Patent No. [CN 000107434778 A, 000107434778]

[4] Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions [J].

Cioc, Razvan C. ;

Preschel, Hans D. ;

van der Heijden, Gydo ;

Ruijter, Eelco ;

Orru, Romano V. A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (23) :7837-7842

[5] Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals [J].

Climent, Maria J. ;

Corma, Avelino ;

Iborra, Sara .

CHEMICAL REVIEWS, 2011, 111 (02) :1072-1133

[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] Chemistry and Biology Of Multicomponent Reactions [J].

Domling, Alexander ;

Wang, Wei ;

Wang, Kan .

CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135

[10] A highly efficient, asymmetric synthesis of benzothiadiazine-substituted tetramic acids: Potent inhibitors of hepatitis C virus RNA-dependent RNA polymerase [J].

Fitch, DM ;

Evans, KA ;

Chai, DP ;

Duffy, KJ .

ORGANIC LETTERS, 2005, 7 (24) :5521-5524

← 1 2 3 4 5 →