Construction of dibenzo[d,f][1,3]oxazepine skeleton from 2′-amino-2-hydroxybiphenyl and isothiocyanates via iodine-mediated cyclodesulfurization
2021
Murata, Yuki | Izawa, Mako | Koyanagi, Arisu | Hayashi, Yukako | Hyodo, Tadashi | Matsumura, Mio | Yamaguchi, Kentaro | Yasuike, Shuji
1,3-Oxazepines are of interest because of their application as biologically active substances. Herein, 2′-amino-2-hydroxybiphenyl was reacted with isothiocyanate-derived thioureas and treated in situ with iodine in the presence of triethylamine to afford dibenzo[d,f][1,3]oxazepine derivatives in good-to-excellent yields. X-ray analysis revealed that the obtained product comprises a 7-membered heterocycle and has a Z-configuration imine moiety in its solid state. All oxazepine derivatives obtained by this reaction are novel compounds.
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