苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法

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文献介绍了一种以苯硼酸为催化剂,无溶剂条件下,以2-甲酰基苯甲酸与伯胺和多种酮(或2-甲酰基苯甲酸与多种酮)为原料,一锅法合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法。该方法与传统方法相比,具有高效,实用,操作简单等优点。

苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第1张


操作

A:  A mixture of 2-formylbenzoic acid (1 mmol) and amine (1mmol) were stirred for 5 min at RT. After this time the ketone compound (1.0 mmol) and PhB(OH)2 (0.1 mmol) were added, and the reaction mixture was stirred at 100 oC. The progress of the reaction was checked by TLC. After completion of the reaction, the mixture was cooled at RT and the resulting crude product was purified by flash column chromatography using hexane-EA mixture as eluent, to give the pure products.
B:  A mixture of 2-formylbenzoic acid (1 mmol) and ketone (1.0mmol) was stirred for 5 min at RT, followed by the addition of PhB(OH)2 (0.1mmol). After this time, the reaction mixture was stirred at 135 oC for the appropriate time and the progress of the reactionwas checked by TLC. After completion, the mixture was cooled at RT and the crude product was purified by flash column chromatography using hexane-EA as eluent, to give the pure products.

3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮类化合物存在于多种天然产物及药物结构中;同时异苯并呋喃-1(3H)-酮类化合物也是有机合成中的重要中间体。该方法为以上两类化合物的合成提供了一种新的思路。

苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第2张

Pagoclone 1为抗焦虑剂,用于治疗惊恐症,同时也用于口吃的治疗;5ꞌ-hydroxypagoclone 2也是一种抗焦虑剂;异苯并呋喃-1(3H)-酮类化合物3常被用作抗结核剂,抗高血压及抗炎剂等,同时也是药物合成中的重要中间体。


普适性考察

苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第3张苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第4张

苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第5张

作者对反应历程进行了描述

苯硼酸为催化剂高效合成3-取代异吲哚-1-酮和异苯并呋喃-1(3H)-酮的方法  第6张

参考文献DOI:10.1016/j.tet.2018.05.086


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