Tetrahedron

Regioselective synthesis of 2-chloro-3-pyridinecarboxylates

TY Zhang, JR Stout, JG Keay, EFV Scriven, JE Toomey…

文献索引：Zhang; Stout; Keay; Scriven; Toomey; Goe Tetrahedron, 1995 , vol. 51, # 48 p. 13177 - 13184

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被引用次数: 34

摘要

2-Chlorocyanoacetate was found to undergo base-catalyzed Michael addition to α, β- unsaturated ketones or aldehydes to afford 5-oxopentenenitrile derivatives. In the presence of anhydrous HCl, these compounds cyclize to yield 2-chloro-3-pyridinecarboxylates. The process is highly regiospecific and useful in the synthesis of 2, 3-disubstituted pyridines.