1146955-52-3Relevant articles and documents
Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles
Li, Ke-Lai,Du, Zong-Bo,Guo, Can-Cheng,Chen, Qing-Yun
scheme or table, p. 3286 - 3292 (2009/09/08)
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpy-rido[2,l-6]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,l-6]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 HC1 to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.