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.
Highlights
The dibenz[b,f]oxepin scaffold is an important synthetic target because a large number of compounds having this skeleton present relevant biological activities; such as antidepressant [1], anxiolytic [2], antipsychotic [3,4], angiotensin-II-receptor-antagonist [5], and anti-inflammatory properties [6]
A number of natural occurring dibenz[b,f]oxepins have been isolated from plants of the genus Bauhinia
We focused our research on the synthesis of a Z-stilbene
Summary
The dibenz[b,f]oxepin scaffold is an important synthetic target because a large number of compounds having this skeleton present relevant biological activities; such as antidepressant [1], anxiolytic [2], antipsychotic [3,4], angiotensin-II-receptor-antagonist [5], and anti-inflammatory properties [6]. Fabaceae) and many of them exhibit important biological activities [7]. Bauhinoxepin A isolated from Bauhinia saccocalyx Pierre (Figure 1), shows antimycobacterial activity [8]. Pettit et al isolated bauhiniastatin 1 from Bauhinia purpurea L., Molecules 2013, 18 which exhibits significant growth inhibition activity against several human cancer lines [9]. Kittakoop et al have described bauhinoxepin J, which shows potent antimycobacterial and antimalarial activities, as well as tumor growth inhibitory activity, against KB cells [10]
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