An Efficient Synthesis of Dibenzo[b,f]oxepins by Ring‐Closing Metathesis

Abstract

DibenzoA C H T U N G T R E N N U N G [b,f]oxepin scaffolds, which have been found in the Bauhinia plant family and have potent medicinal properties, have been prepared efficiently by a two-step protocol that involves Ullmann-type coupling and ring-closing metathesis reactions.

Exciting progress in the transition metal‐catalyzed synthesis of oxepines, benzoxepines, dibenzoxepines, and other derivatives

“…In 2013, Bharath et al described a two-step procedure for the synthesis of dibenzo[b,f]oxepines 190 through copper-catalyzed Ullmann coupling and ring-closing metathesis by Grubbs' catalyst in dichloromethane (DCM) reflux (Scheme 54). [94] A direct synthesis of tricyclic compounds and the tolerance of various functional groups are the advantages of this strategy. Doveston et al in 2012 presented the total synthesis of (±)-janoxepin analogs 196 as antiplasmodial D-leucinederived oxepine-pyrimidinone-ketopiperazine.…”

Synteza Pochodnych Dibenzo[b,f]oksepiny Podstawionych W Pierścieniu Aromatycznym

“…Pochodną artocarpolu A jest natomiast artocarpol G (rys. 4), który, jak dowiedziono, silnie hamuje uwalnianie β-glukoronidazy i histaminy pochodzących z degranulacji komórek tucznych [7]. Podstawione dibenzo[b,f]oksepiny charakteryzują się tym, że wykazują silne właściwości antypsychotyczne [5,8,9], przeciwzapalne [5,10], przeciwdepresyjne [5,11], owadobójcze [5,12], przeciwpadaczkowe [5,13] czy też antyhipertensyjne [5].…”

Pd/C and TFA‐promoted One‐pot, Two‐step Cascade Reaction: An Effective Synthesis of Oxepines

“…Recently, synthesis of bioactive oxepines were reported by Nishino et al ., [15] Guy et al ., [16] Heo et al [17] . and Mohapatra et al [18] …”

“…[13] In 2014, Jana et al [14] successfully developed FeCl 3 -catalyzed alkyne-aldehyde metathesis process for the synthesis of acylated dibenzo[b,f]oxepines from 2-(2-(phenylethynyl)phenoxy)benzaldehyde derivatives. Recently, synthesis of bioactive oxepines were reported by Nishino et al, [15] Guy et al, [16] Heo et al [17] and Mohapatra et al [18] Of late, Panda and coworkers described the synthesis of phenyldibenz[b,f]oxepines in two steps involving Sonagashira reaction between o-iododiaryl ethers and terminal alkyne to give 2-phenoxy diaryl acetylenes in the first step, followed by FeCl 3 -catalyzed intramolecular CÀ H hydroarylation in the second step (Scheme 1a). [19a] Later, Yao and coworkers demonstrated on the synthesis of substituted dibenzo[b,f]oxepine-10carbonitrile via copper-catalyzed cascade reaction of 2-halo benzaldehydes with 2-iodobenzylcyanide, however, the scope of the method was limited (Scheme 1b).…”