Abstract
ABSTRACT
2-Formyl-D-xylal (1A) and 2-formyl-L-arabinal (1B) were reacted with alkyl cyanoacetates to furnish the 1,5-anhydro-3,4-di-O-benzyl-2-[(E)-2-cyano-2-alkoxycarbonylvinyl]-2-deoxy-D(L)-hex-1-enitols 2A and 2B, respectively. Treatment of 2A, 2B with aromatic amines afforded the 1-aryl-5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydro-2-oxopyridine-3-carbonitriles 3A-C. Ring transformation of 1A, 1B with N-substituted oxobutyramides, dialkyl 3-oxopentanedioate and benzimidazol-2-ylacetonitrile yielded the 3-acetyl-1-aryl-5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyridin-2-ones 6A-D, alkyl 5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-2-hydroxyisophthalates 8A-D and 2-[1,2-bis(benzyloxy)-3-hydroxypropyl]benzo[4,5]imidazo-[1,2-A]-pyridine-4-carbonitriles 11A, 11B, respectively.