The Guareschi-Thorpe Cyclization Revisited - An Efficient Synthesis of Substituted 2,6-Dihydroxypyridines and 2,6-Dichloropyridines

被引：3

作者：

Eriksson, Magnus C. ^{[1
]}

Zeng, Xingzhong ^{[1
]}

Xu, Jinghua ^{[1
]}

Reeves, Diana C. ^{[1
]}

Busacca, Carl A. ^{[1
]}

Farina, Vittorio ^{[2
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, 900 Old Ridgebury Rd,POB 368, Ridgefield, CT 06877 USA

[2] Janssen Pharmaceut PRD, Turnhoutseweg 30, B-2340 Beerse, Belgium

来源：

SYNLETT | 2018年 / 29卷 / 11期

关键词：

fluoroalkyl compounds; ss-keto esters; DBU; pyridines; chlorination; Guareschi-Thorpe cyclization; DERIVATIVES;

D O I：

10.1055/s-0037-1609685

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DBU as base is key in a practical modified Guareschi-Thorpe cyclization of ss-keto esters and 2-cyanoacetamide to allow the synthesis of substituted pyridones in good to excellent yields. The chlorination of DBU salts of pyridones with POCl3 in the presence of a quaternary ammonium salt under standard atmospheric reflux conditions as opposed to the typical pressure equipment led to high yields of substituted 2,6-dichloropyridines.

引用

页码：1455 / 1460

页数：6

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