Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition

被引：15

作者：

Zou, Wei ^{[1
]}

Bhasin, Milan ^{[1
]}

Vembaiyan, Kannan ^{[1
]}

Williams, Dean T. ^{[1
]}

机构：

[1] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 08期

关键词：

Synthesis; Triazole; C-Glycoside; Nitroalkene; Cycloaddition; Michael addition; TERMINAL ALKYNES; AZIDES; ANALOGS;

D O I：

10.1016/j.carres.2009.03.007

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A synthetic method to triazole-fused sugars by treatment of nitroalkene-containing C-glycosides with sodium azide is described. Initial experiments conducted at room temperature gave only the 1,3-dipolar cycloaddition products. However, at elevated reaction temperature the tandem beta-elimination/cycloaddition/Michael addition yielded 1,5-disubstituted triazole-fused sugars. (C) 2009 Published by Elsevier Ltd.

引用

页码：1024 / 1027

页数：4

共 26 条

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[23] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .33. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES IN WHICH THE DIPOLAROPHILE IS LOCATED WITHIN THE OXIME
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[24] Straightforward Strategy for the Stereoselective Synthesis of Spiro-Fused (C-5)Isoxazolino- or (C-3)Pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman Adducts by 1,3-Dipolar Cycloaddition and Reductive Cyclization
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[25] Tandem C-2 Functionalization-Intramolecular Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction: A Convenient Route to Highly Diversified 9H-Benzo[b]pyrrolo[1,2-g][1,2,3]triazolo[1,5-d[1,4]diazepines
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[26] SYNTHESIS OF NOVEL FUSED BETA-LACTAMS BY INTRAMOLECULAR 1,3-DIPOLAR CYCLO-ADDITIONS .7. (9RS,9ARS)-9,9A-DIHYDRO-5-METHYL-8-OXO-9-PHENOXYACETAMIDO-8H-AZETO[1,2-A]-V-TRIAZOLO[5,1-C]PYRAZINE-6-CARBOXYLIC ACIDS AND (3BRS,4RS,7SR)-4,5-DIHYDRO-5-OXO-4-PHENOXYACETAMIDO-3BH-AZETO[1',2'-3,4]-IMIDAZO[1,5-C]-V-TRIAZOLE-7-CARBOXYLIC ACID,
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