碲引发环化合成香豆素、4-羟基香豆素和4-羟基喹啉酮。

Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations.

作者信息

Dittmer Donald C, Li Qun, Avilov Dimitry V

机构信息

Department of Chemistry, Syracuse University, Room 1-014 CST, Syracuse, New York 13244, USA.

出版信息

J Org Chem. 2005 Jun 10;70(12):4682-6. doi: 10.1021/jo050070u.

DOI:10.1021/jo050070u

PMID:15932305

Abstract

Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2(1H)-ones can be conveniently prepared by treatment of alpha-halocarboxylic acid esters of salicylaldehyde, o-hydroxyacetophenone, methyl salicylate, and methyl N-methyl- or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the alpha-chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment with benzylamine. Elemental tellurium may be recovered and reused.

摘要

香豆素、4-羟基香豆素和4-羟基喹啉-2(1H)-酮可通过用碲化钠或碲化锂处理水杨醛、邻羟基苯乙酮、水杨酸甲酯以及N-甲基-或N-苯基邻氨基苯甲酸甲酯的α-卤代羧酸酯方便地制备。正如用水杨酸甲酯的α-氯苯乙酸酯与苄胺进行的捕获实验所表明的，苯基乙烯酮的形成与水杨酸甲酯的α-氯苯乙酸酯的环化相互竞争。元素碲可以回收再利用。