One-Pot Synthesis of Semisaturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-09 DOI:10.1002/ejoc.202401005

Song Xie, jilai Wu, Likai Zhou, Chao Wei, Xiaoliu Li, Hua Chen

引用次数: 0

Abstract

Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.

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通过 Diels-Alder 反应一锅合成半饱和融合多环氨基糖

摘要：在加热条件下，通过 D-核糖对甲苯磺酸盐、苯胺和环烯酮的单锅立体选择性三组分反应合成了一系列半饱和融合多环亚氨基糖。由亚胺离子衍生的 N-芳基烯胺是反应的关键中间体。通过这种方法，在 80 °C 下通过正常的 Diels-Alder 机理获得了各种新型复合融合亚氨基糖。这种策略将有助于制备具有结构多样性的生物活性亚氨基糖类似物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.