Related Experiment Video
Updated: Jan 10, 2026

Original Experimental Approach for Assessing Transport Fuel Stability
Published on: October 21, 2016
Furan Oxidation-Cyclization to Oxazepines: Favoring 7-exo-trig over 6-endo-trig and 5-exo-trig Trajectories
Fatma Albayrak Halac1, Busra Nur Aydın Kandemir1,2, Hasan Secen2
1Department of Chemistry, Faculty of Science, Gebze Technical University, Gebze, Kocaeli 41400, Türkiye.
Abstract:
The sequential oxidation-cyclization of hydroxyaminoalkylfurans to oxazepines is controlled by a regioselective 7-exo-trig cyclization rather than the usually more favorable, 6-endo-trig and 5-exo-trig cyclizations. The key trajectory determinant is the generation of Z-dienones, which place the terminal substituents in close proximity. The versatile furan approach to oxazepines exploits an underdeveloped stereochemical feature allowing an efficient, regioselective, and robust route to variously substituted oxazepines ideal for bioactive discovery.
Related Concept Videos
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
Thermal and Photochemical Electrocyclic Reactions: Overview
Phase I Oxidative Reactions: Overview
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility

