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在无溶剂条件下,聚苯乙烯负载的对甲苯磺酸催化的一种用于密集官能化吲哚基4H-色烯的无金属串联C-C/C-O键形成方法。

A metal-free tandem C-C/C-O bond formation approach to densely functionalized indolyl 4H-chromenes catalyzed by polystyrene-supported p-toluenesulfonic acid under solvent-free conditions.

作者信息

Shinde Vijay Vilas, Jeong Yong Seok, Jeong Yeon Tae

机构信息

Department of Image Science and Engineering, Pukyong National University, Busan, 608-737, Republic of Korea.

出版信息

Mol Divers. 2015 May;19(2):367-83. doi: 10.1007/s11030-015-9579-1. Epub 2015 Mar 24.

DOI:10.1007/s11030-015-9579-1
PMID:25802172
Abstract

A new environmentally benign and highly convergent protocol for the synthesis of indolyl 4H-chromene derivatives has been developed. This one-pot three-component condensation reaction of salicylaldehyde, cyclic 1,3-diketones, and indole is promoted by PS-PTSA as a reusable heterogeneous acid catalyst under solvent-free conditions. This protocol demonstrates several notable advantages such as that the catalyst is readily available and can be recovered and reused for at least five runs without any significant impact on product yields, high atom economy, excellent yields, and efficiency of producing three new bonds (two C-C and one C-O) and one stereo center in a single operation.

摘要

已经开发出一种用于合成吲哚基-4H-色烯衍生物的新型环境友好且高度汇聚的方法。在无溶剂条件下,以聚苯乙烯-对甲苯磺酸(PS-PTSA)作为可重复使用的多相酸催化剂,促进水杨醛、环状1,3-二酮和吲哚的一锅三组分缩合反应。该方法具有几个显著优点,例如催化剂易于获得,可回收并重复使用至少五次,且对产物收率没有任何显著影响;原子经济性高、产率优异,并且能够在一次操作中高效地生成三个新键(两个C-C键和一个C-O键)以及一个立体中心。

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