(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine

Abstract

The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclization-methoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1H-NMR, 13C-NMR spectroscopies, MS spectrometry, and elemental analysis. The Z configuration around the double bond was unequivocally established by 2D NOESY experiments.

Keywords

• palladium
• benzoxazines
• carbonylation
• Heterocyclization
• 2D NMR experiments