Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage.,Organic Letters

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Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage.
Organic Letters ( IF 4.9 ) Pub Date : 2020-04-27 , DOI: 10.1021/acs.orglett.0c01214
Maryne A J Dubois ₁ , Milo A Smith ₁ , Andrew J P White ₁ , Alvin Lee Wei Jie ₁ , James J Mousseau ₂ , Chulho Choi ₂ , James A Bull ₁

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Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, azetidines, and cyclobutanes are prepared in two steps: a catalytic Friedel–Crafts reaction from four-membered ring alcohol substrates, followed by mild oxidative cleavage. The suitability of the products as building blocks is reflected in their facile purification and amenability to derivatization. Examples include heteroaromatics and aryltriflates, as well as oxetane-derived profen drug analogues and a new endomorphin derivative containing an azetidine amino acid residue.

中文翻译：

通过选择性呋喃氧化裂解短时间合成氧杂环丁烷和氮杂环丁烷3-芳基-3-羧酸衍生物。

尽管四元环为药物化学提供了引人注目的理化性质，但它们仍然是未开发的基序。带有氧杂环丁烷，氮杂环丁烷和环丁烷的丙烯酸可以分两个步骤制备：从四元环醇底物进行的Friedel-Crafts催化反应，然后进行温和的氧化裂解。产品作为构建基块的适用性体现在其易于纯化和易于衍生化方面。实例包括杂芳族化合物和芳基三氟甲磺酸酯，以及氧杂环丁烷衍生的芬芬药物类似物和含有氮杂环丁烷氨基酸残基的新内啡肽衍生物。

更新日期：2020-04-27

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