A Facile Synthesis of 4,6,7,8,8a,9-Hexahydropyrrolo[1,2-a][1,2,3]triazolo[1,5-d]pyrazines by a Three-Component Coupling Reaction Followed by Intramolecular 1,3-Dipolar Cycloaddition

被引：24

作者：

Dhondge, Attrimuni P. ^{[1
]}

Afraj, Shakil N. ^{[1
]}

Nuzlia, Cut ^{[1
]}

Chen, Chinpiao ^{[1
]}

Lee, Gene-Hsian ^{[2
]}

机构：

[1] Natl Dong Hwa Univ, Dept Chem, Soufeng 974, Hualien, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 10617, Taiwan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 19期

关键词：

Nitrogen heterocycles; Multicomponent reactions; Cyclization; Cycloaddition; Propargylic compounds; C-H ACTIVATION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ONE-POT SYNTHESIS; DIRECT ADDITION; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; PROPARGYLAMINES; ALDEHYDE;

D O I：

10.1002/ejoc.201300226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and efficient two-step protocol for the synthesis of several new 4,6,7,8,8a,9-hexahydropyrrolo[1,2-a][1,2,3]triazolo[1,5-d]pyrazines is described. The first step involves the AuBr3-catalyzed three-component coupling reaction of terminal alkynes, aldehydes, and amines under solvent-free conditions to provide the requisite propargylamines. The reaction tolerates a high structural diversity, requires only short reaction times, gives high diastereoselectivities, and is environmentally benign. Furthermore, the propargylamine products undergo catalyst-free intramolecular azide-alkyne [3 + 2] dipolar cycloaddition reactions to give the 4,6,7,8,8a,9-hexahydropyrrolo[1,2-a][1,2,3]triazolo[1,5-d]pyrazines in excellent yields and with excellent diastereoselectivities.

引用

页码：4119 / 4130

页数：12

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