Hypervalent iodine-mediated intramolecular alkene halocyclisation

• Charu Bansal,
• Oliver Ruggles,
• Albert C. Rowett and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

• intermediate A. The product is formed following a 6-endo cyclisation with nucleophilic attack from oxygen to provide the fluoro-benzoxazepines 30. In 2015, Stuart and co-workers reported an intramolecular fluorocyclisation of unsaturated carboxylic acids 24 (Scheme 14) [38]. Using 1-fluoro-3,3

• of unsaturated alcohols and carboxylic acids to make tetrahydrofurans, fluoromethyl-γ-lactones and tetrahydropyrans. The ratio of stereoisomers is shown in parentheses. Oxyfluorination of unsaturated alcohols. Synthesis and mechanism of fluoro-benzoxazepines. Intramolecular fluorocyclisation of

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• -fused benzodiazepines, benzoxazepines, or benzothiazepines exhibit unique biological and pharmacological properties [22][23]. For example, midazolam is a hypnotic-sedative drug with anxiolytic, muscle relaxant, and anticonvulsant properties [24], flumazenil is made to induce general anesthesia for

• conditions, we next studied the scope of this reaction with substituted benzoxazepines, gem-diactivated olefins, and isocyanide derivatives (Scheme 3). As illustrated in Scheme 3, both electron-donating (-Me, -OMe) and electron-withdrawing (-NO2, Cl, and Br) groups were well tolerated under the optimal

• general, a significant increase in the yield of the products was observed compared to the submillimole state. Physical properties The compounds such as benzoxazepines, benzothiazepines, benzodiazepines, and pyrrole have shown promising applications in optoelectronics, biophotonics, and cell imaging due to

Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction

• László Tóth,
• Yan Fu,
• Hai Yan Zhang,
• Attila Mándi,
• Katalin E. Kövér,
• Tünde-Zita Illyés,
• Attila Kiss-Szikszai,
• Balázs Balogh,
• Tibor Kurtán,
• Sándor Antus and
• Péter Mátyus

Beilstein J. Org. Chem. 2014, 10, 2594–2602, doi:10.3762/bjoc.10.272

• neuroprotective condensed 2-phenyl-1,4-benzoxazepines rac-7a,b through the diastereoselective domino Knoevenagel–1,5-hydride shift cyclization reaction rac-5→rac-7a,b from the readily available 4-aryl-2-phenyl-1,4-benzoxazepine derivative, rac-5 (Scheme 1). Ring-closure transformations involving C(sp3)–H bond

• –35-induced neurotoxicity in SH-SY5Y cells. ##P < 0.01 vs control group, **P< 0.01 vs β-amyloid25–35 group. Domino Knoevenagel–[1,5]-hydride shift cyclization reaction for the preparation of condensed 1,4-benzoxazepines. i) a) NaN3, CF3COOH, b) H2O, Δ (77%); ii) LiAlH4, dry THF, Δ (80%); iii) 11b

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

• Lisa Moni,
• Luca Banfi,
• Andrea Basso,
• Alice Brambilla and
• Renata Riva

Beilstein J. Org. Chem. 2014, 10, 209–212, doi:10.3762/bjoc.10.16

• derivatives. Keywords: benzoxazepines; diversity-oriented synthesis; multicomponent reactions; Mitsunobu reaction; Ugi reaction; Introduction Although the classical Ugi 4-component reaction (U-4CR) leads to acyclic peptide-like compounds, post-condensation cyclizations can afford a huge variety of drug-like

Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

• Luca Banfi,
• Andrea Basso,
• Valentina Cerulli,
• Valeria Rocca and
• Renata Riva

Beilstein J. Org. Chem. 2011, 7, 976–979, doi:10.3762/bjoc.7.109

• membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines. Keywords: benzoxazepines; cyclic imines; long range stereoinduction; multicomponent reactions; Ugi reaction; Introduction The Ugi reaction is probably the most renowned and widely used

• good yields, nine different tetrahydro[f][1.4]benzoxazepines 6, equipped with three diversity points. As shown in Table 1, all the tested Ugi reactions proceeded with remarkably high diastereoselectivity, if one considers that the R1 substituent is quite far away from the imine carbon. This long range