The synthesis and mass spectra of 3-hydroxy-2,3,4,5-tetrahydro-1,5-benzoxazepine and related compounds

1,5‐Benzoxazepines as a unique and potent scaffold for activity drugs: A review

“…The starting material is o-nitrophenol 16, which reacts with epichlorohydrin, and an obtained epoxy derivative 17 is transformed into a benzoxazepine derivative 18 under catalytic reduction in the presence of palladium on activated charcoal (Scheme 5). [24,25] Synthesis of polycyclic 1,5-benzoxazepine with a five-or six-membered heterocycle fused to a seven-membered ring at the benzoxazepine moiety is a useful compound in drug research.…”

Synthesis and chemical transformations of 1,4‐, 4,1‐, and 1,5‐benzoxazepines

“…3-Hydroxy-5-(methylsulphonyl)-2,3,4,5-tetrahydro-1,5benzoxazepine (92) has been prepared by the cyclization of the N-mesylated 2-aminophenol derivative 91 (Scheme 31) [52]. Compound 92 was then demesylated to afford the 3-hydroxy-2,3,4,5-tetrahydro-1,5-benzoxazepine (93).…”

“…However, the N-alkylation of the 2,3-dihydro-1,5-benzoxazepin-4(5H)-one type compounds is well documented in the literature [51,52,57,[69][70][71]73,79]. The starting 1,5benzoxazepine 140 is generally allowed to react with the apropriate alkyl halide in anhydrous dimethylformamide in the presence of sodium hydride to afford the N-alkylated derivatives 141 (Scheme 48).…”

Matrix‐assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3‐dihydro‐1,4‐benzoxazepines

“…Several benzoxazepine derivatives have been shown to exhibit various biological and pharmacolocigal effects such as analgetic, spasmolytic, antihistamine and sedative activities 1–6. Due to these diverse activities, a range of benzoxazepines was synthesized7–13 and the fragmentation behavior under electron ionization (EI) examined 14–16. In our earlier studies,7, 8 we showed that benzoxazepines can readily be prepared by the well‐known Schmidt reaction of flavanoid derivatives.…”