Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

• DOI: 10.1021/acs.orglett.1c02895
• Publication Date: 2021-10-14T04:59:54Z
• Authors: Arnab Ghosh; Rajeev V. Hegde; Haridas B. Rode; Ram Ambre; Manoj V. Mane; Siddappa A. Patil; Balasubramanian S...; Ramesh B. Dateer
• Keywords: 01 natural sciences; 0104 chemical sciences

An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer formation new C═O, C-N, C-O bonds occur at room temperature to form six-, seven-, eight-membered heterocycles one-pot reaction without using an external oxidant base. The photophysical properties are studied ultraviolet-visible absorption photoluminescence. mechanistic elucidation well supported by control experiment literature precedents.