Abstract

The title compounds were first synthesized in considerably good yields by acid-catalyzed dehydration of the corresponding ethyl 2-arylcarbonyl-3-hydroxy-3-phenyl-2,3-dihydrooxepino[2,3-b]indolizin-4-carboxylate derivatives with methanesulfonic acid in boiling chloroform. Although these full-conjugated oxepino[2,3-b]indolizines with a nonaromatic 16π electron system were stable at room temperature, upon heating them in boiling ethanol, they were smoothly rearranged to ethyl 2-arylcarbonyl-1-oxo-2-phenyl-1,2-dihydropyrido[1,2-a]indole-3-carboxylates in good yields. The structures of these oxepino[2,3-b]indolizines and the rearranged pyrido[1,2-a]indol-1(2H)-ones were distinctly determined by physical and spectral means, including X-ray analyses.

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