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Molbank 2017, 2017(1), M927; doi:10.3390/M927

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

1
Department of Chemistry, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
2
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Norbert Haider
Received: 20 December 2016 / Revised: 5 January 2017 / Accepted: 9 January 2017 / Published: 13 January 2017
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: palladium; benzoxazines; carbonylation; Heterocyclization; 2D NMR experiments palladium; benzoxazines; carbonylation; Heterocyclization; 2D NMR experiments
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MDPI and ACS Style

Pancrazzi, F.; Motti, E.; Costa, M.; Mancuso, R.; Gabriele, B.; Della Ca’, N. (Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine. Molbank 2017, 2017, M927.

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