Synthesis of Polysubstituted Pyrroles through the Tandem 1,3-Addition/5-endo-dig Cyclization of 1-(1-Alkynyl)cyclopropyl Imines

被引：14

作者：

Urbanaite, Aurelija ^{[1
]}

Cikotiene, Inga ^{[1
]}

机构：

[1] Vilnius Univ, Dept Organ Chem, Fac Chem, Naugarduko 24, LT-03225 Vilnius, Lithuania

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 31期

关键词：

Alkynes; Small-ring systems; Cyclization; Nitrogen heterocycles; Imines; HIGHLY SUBSTITUTED FURANS; NATURAL-PRODUCTS; ELECTROPHILIC CYCLIZATION; MODULAR ENTRY; 1-(1-ALKYNYL)-CYCLOPROPYL KETONES; CYCLOADDITION REACTIONS; BIOLOGICAL-ACTIVITY; NITRONES; ALKYNES; NUCLEOPHILES;

D O I：

10.1002/ejoc.201600985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropyl-tethered 3-alkynyl imines react with polarized-covalent-bond-containing compounds to give polyfunctionalized pyrroles. This provides a mild and effective method for the simultaneous introduction of halogen, chalcogen, or hydrogen groups to the 3-position of the pyrrole ring, together with the incorporation of halogen, azide, or alkoxy/aryloxy groups into the ethyl side-chain.

引用

页码：5294 / 5300

页数：7

共 65 条

[31]

Hassner A., 2005, ENCY REAGENTS ORGANI

[32] Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products [J].

Hu, Dennis X. ;

Withall, David M. ;

Challis, Gregory L. ;

Thomson, Regan J. .

CHEMICAL REVIEWS, 2016, 116 (14) :7818-7853

[33] Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective lodocyclization of Ynamides [J].

Huang, Hai ;

Zhu, Xiaolin ;

He, Guangke ;

Liu, Qi ;

Fan, Junzhen ;

Zhu, Hongjun .

ORGANIC LETTERS, 2015, 17 (10) :2510-2513

[34] An efficient synthesis of highly substituted furans via the electrophilic cyclization of 1-(1-alkynyl)-cyclopropyl ketones [J].

Huang, Xian ;

Fu, Weijun ;

Miao, Maozhong .

TETRAHEDRON LETTERS, 2008, 49 (15) :2359-2362

[35] Synthesis and biological activity of pyrrole analogues of combretastatin A-4 [J].

Jung, Eun-Kyung ;

Leung, Euphemia ;

Barker, David .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (13) :3001-3005

[36] A Unique Cascade Reaction between 3-Arylprop-2-inylcarboxylates and Benzaldehydes Leading to the Formation of Morita-Baylis-Hillman Adducts [J].

Karpaviciene, Ieva ;

Cikotiene, Inga .

ORGANIC LETTERS, 2013, 15 (01) :224-227

[37] Synthesis of Pyrroles through Rhodium(III)-Catalyzed Reactions of Allylamines and Alkenes [J].

Kim, Dong-Su ;

Seo, Yong-Sik ;

Jun, Chul-Ho .

ORGANIC LETTERS, 2015, 17 (15) :3842-3845

[38] Stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles [J].

Labsch, Stephan ;

Ye, Shute ;

Adler, Andreas ;

Neudoerfl, Joerg-Martin ;

Schmalz, Hans-Guenther .

TETRAHEDRON-ASYMMETRY, 2010, 21 (13-14) :1745-1751

[39]

Larock RC, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, P51

[40] Synthesis of Multiple-Substituted Pyrroles via Gold(I)-Catalyzed Hydroamination/Cyclization Cascade [J].

Li, Xiangdong ;

Chen, Ming ;

Xie, Xin ;

Sun, Ning ;

Li, Shi ;

Liu, Yuanhong .

ORGANIC LETTERS, 2015, 17 (12) :2984-2987

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