title: Synthesis of 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via Four-component reactions of aromatic aldehydes, cyclic 1,3-carbonyls, arylamines, and dimethyl acetylenedicarboxylate.
abstract: A protocol has been developed for the efficient synthesis of structurally diverse 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via four-component reactions of arylamines, acetylenedicarboxylate, aromatic aldehydes and cyclic 1,3-diketones. The selective formation of the very different pyridinone or pyran derivatives depends on the structure of cyclic 1,3-diketone. The key steps are proposed to involve Michael addition of the enamino ester formed in situ from the reaction of arylamine with dimethyl acetylenedicarboxylate to arylidine cyclic 1,3-diketones.
authors.affiliation: College of Chemistry & Chemical Engineering, Yangzhou University, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Sun
authors.forename: Er-Yan
authors.initials: EY
authors.lastname: Xia
authors.forename: Qun
authors.initials: Q
authors.lastname: Wu
authors.forename: Chao-Guo
authors.initials: CG
authors.lastname: Yan
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D055808:Drug Discovery; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D011728:Pyridones / Q000138:chemical synthesis*; D054852:Small Molecule Libraries / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D011714:Pyrans; D011728:Pyridones; D054852:Small Molecule Libraries; C022918:acetylenedicarboxylic acid dimethyl ester