FeCl 3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused oxepines/azepines and their cytotoxic activity

• Published in: Organic & biomolecular chemistry 2017-05, Vol.15 (20), p.4468-4476
• Main Authors: Shiva Kumar, K, Siddi Ramulu, Meesa, Rajesham, Bandari, Kumar, N Praveen, Voora, Vani, Kancha, Rama Krishna
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Azepines - chemical synthesis; Azepines - chemistry; Azepines - pharmacology; Catalysis; Cell Line, Tumor; Cell Proliferation - drug effects; Chlorides - chemistry; Crystallography, X-Ray; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Ferric Compounds - chemistry; HeLa Cells; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Heterocyclic Compounds - pharmacology; Humans; Indoles - chemistry; Indoles - pharmacology; MCF-7 Cells; Models, Molecular; Molecular Structure; Oxepins - chemical synthesis; Oxepins - chemistry; Oxepins - pharmacology; Structure-Activity Relationship
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/C7OB00715A

Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl . The reaction proceeded via C-C bond followed by C-X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.