Tetrahedron p. 13177 - 13184 (1995)
Update date:2022-08-11
Topics:
Zhang
Stout
Keay
Scriven
Toomey
Goe
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.
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