title: Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles.
abstract: o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2'-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HCl to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.
authors.affiliation: College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
authors.forename: Ke-Lai
authors.initials: KL
authors.lastname: Li
authors.forename: Zong-Bo
authors.initials: ZB
authors.lastname: Du
authors.forename: Can-Cheng
authors.initials: CC
authors.lastname: Guo
authors.forename: Qing-Yun
authors.initials: QY
authors.lastname: Chen