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Convenient two-step synthesis of highly functionalized benzo-fused 1,4-diazepin-3-ones and 1,5-diazocin-4-ones by sequential Ugi and intramolecular SNAr reactions
Tetrahedron ( IF 2.1 ) Pub Date : 2017-09-18 , DOI: 10.1016/j.tet.2017.09.028
Simon Vézina-Dawod , Nicolas Gerber , Xinxia Liang , Eric Biron

Benzodiazepinones are an important family of heterocycles with very attractive pharmacological properties and peptidomimetic abilities. We report herein a rapid and efficient two-step synthesis of polysubstituted 1,4-benzodiazepin-3-ones and 1,5-benzodiazocin-4-ones using a multicomponent condensation/cyclization strategy. The approach uses an Ugi four-component reaction to condense readily available Nα-Fmoc-amino acids, amines and isocyanides with a 2-fluorobenzaldehyde derivative followed by a one-pot Fmoc-group removal, intramolecular aromatic nucleophilic substitution for ring closure and side chain deprotection. The described method gives access to benzo-fused 7- and 8-membered rings bearing a wide variety of functionalized substituents and was applied to efficiently prepare tri- and tetrasubstituted 1,4-benzodiazepin-3-ones and 1,5-benzodiazocin-4-ones in high yields in two straightforward steps.



中文翻译:

通过连续的Ugi和分子内S N Ar反应方便地两步合成高度官能化的苯并稠合的1,4-二氮杂3-3-酮和1,5-二氮杂-4-酮

苯并二氮杂pin酮是重要的杂环族,具有非常诱人的药理特性和拟肽能力。我们在此报告了一种使用多组分缩合/环化策略快速有效地两步合成多取代的1,4-苯并二氮杂-3-酮和1,5-苯并二氮杂-4-酮的方法。该方法使用的Ugi四组分反应以冷凝容易获得Ñ α-带有2-氟苯甲醛衍生物的-Fmoc-氨基酸,胺和异氰酸酯,然后一锅去除Fmoc-基团,分子内芳族亲核取代基用于闭环和侧链脱保护。所描述的方法可接近带有多种官能化取代基的苯并稠合的7和8元环,并用于有效制备三和四取代的1,4-苯并二氮杂-3-酮和1,5-苯并重氮-4 -通过两个简单的步骤即可获得高产量。

更新日期:2017-09-18
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