title: Unexpected three-component domino synthesis of pyridin-2-ones catalyzed by promiscuous acylase in non-aqueous solvent.
abstract: The Acylase "Amano" (AA)-catalyzed synthesis of valuable pyridin-2-ones via domino Knoevenagel condensation-Michael addition-intramolecular cyclization-oxidization reaction between aldehyde, cyanoacetamide and ethyl acetoacetate or cyclohexyl acetoacetate was developed in the sense of a one-pot strategy. Various aliphatic, aromatic and hetero-aromatic pyridin-2-ones could also be produced in the reaction. The mechanism was illustrated according to the controlled reaction, pyridin-2-one was formed via the oxidization by oxygen at the final step. This simple and efficient enzymatic domino reaction not only widens its application of AA to organic synthesis, but is also an attractive way for the synthesis of heterocyclic compounds.
authors.affiliation: Department of Chemistry, Zhejiang University, No. 38 Zheda Road, Hangzhou 310027, People's Republic of China.
authors.forename: Zhi-Qiang
authors.initials: ZQ
authors.lastname: Liu
authors.forename: Zi-Wei
authors.initials: ZW
authors.lastname: Xiang
authors.forename: Qi
authors.initials: Q
authors.lastname: Wu
authors.forename: Xian-Fu
authors.initials: XF
authors.lastname: Lin
mesh_terms: D000090:Acetoacetates / Q000737:chemistry / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D000581:Amidohydrolases / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D003500:Cyclization; D011728:Pyridones / Q000138:chemical synthesis*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D000090:Acetoacetates; D000447:Aldehydes; D011728:Pyridones; D012997:Solvents; D000581:Amidohydrolases; C019665:amidase