Journal article
Furan Oxidation-Cyclization to Oxazepines: Favoring 7-exo-trig over 6-endo-trig and 5-exo-trig Trajectories
Organic letters, v 27(49), pp 13408-13411
28 Nov 2025
PMID: 41312843
Featured in Collection : UN Sustainable Development Goals @ Drexel
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.
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Details
- Title
- Furan Oxidation-Cyclization to Oxazepines: Favoring 7-exo-trig over 6-endo-trig and 5-exo-trig Trajectories
- Creators
- Fatma Albayrak Halac - Gebze Tech Univ, Fac Sci, Dept Chem, TR-41400 Gebze, Kocaeli, TurkiyeBusra Nur Aydin Kandemir - Gebze Tech Univ, Fac Sci, Dept Chem, TR-41400 Gebze, Kocaeli, TurkiyeHasan Secen - Atatürk UniversityFraser F. Fleming - Drexel University, ChemistryRamazan Altundas - Atatürk University
- Publication Details
- Organic letters, v 27(49), pp 13408-13411
- Publisher
- Amer Chemical Soc
- Number of pages
- 4
- Grant note
- 119Z060 / Trkiye Bilimsel ve Teknolojik Arastirma Kurumu
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:001627290700001
- Scopus ID
- 2-s2.0-105024809201
- Other Identifier
- 991022135743804721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic