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

Author:

Eriksson Magnus1,Zeng Xingzhong1,Xu Jinghua1,Reeves Diana1,Busacca Carl1,Farina Vittorio2,Senanayake Chris1

Affiliation:

1. Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc.

2. Janssen Pharmaceuticals PRD

Abstract

DBU as base is key in a practical modified Guareschi–Thorpe cyclization of β-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.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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