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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
New short strategy for the synthesis of the dibenz[b,f]oxepin scaffold
David R R Moreno, Giorgio Giorgi, Cristian O Salas
1Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago 7820436, Chile. rtapia@uc.cl.
Abstract:
In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular SNAr and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehydes with fluorobenzaldehydes without catalysts. Application of an intramolecular McMurry reaction to the synthesized diarylethers using TiCl4/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%-55% yields.
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