Synthesis of Tetrahydropyridine Derivatives through a Modular Assembly Reaction Using 3,4-Dihydropyran as Dual Substrate and Template

A concise method to synthesize 1,2,3,4-tetrahydropyridines is described that involves the use of 2-alkoxy-3,4-dihydropyran as a modular precursor to react with aniline and a nucleophile. In this method, the heteroatom of the dihydropyran ring was replaced by nitrogen of aniline while the nucleophile attached to its adjacent position. Various druglike polyheterocycles were prepared with this method by using NH2-containing 1,5- or 1,4-bisnucleophiles.