Синтетичний доступ до конденсованих 6,7,8,9-тетрагідро-5Н-піридоазепінів: оцінювання стратегій циклізації

• Date: 2026
• Main Authors: Solod, Bohdan Yu., Vovk, Mykhailo V.
• Format: Article
• Language: English
• Published: National University of Pharmacy 2026
• Subjects: піридоазепан; конденсовані гетероцикли; реакції циклізації; синтетична доступність; органічний синтез
• Online Access: https://ophcj.nuph.edu.ua/article/view/354129
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

The synthetic accessibility of fused pyridoazepane frameworks was investigated through a series of strategies designed to construct differently fused azepane systems. Several precursor designs enabling alternative ring-closure topologies were explored. A “lactam” pathway proved synthetically inaccessible under various conditions due to chemoselectivity issues and competing intermolecular processes. In contrast, an efficient route to the 6,7,8,9-tetrahydro-5H-pyrido[3,2-c]azepine framework was achieved via an intramolecular cyclization strategy, in which the amine functionality was introduced prior to ring assembly. The developed route proceeds under practical laboratory conditions using inexpensive reagents and was demonstrated on a gram scale. These findings provide insight into the structural factors governing ring-closure efficiency in pyridoazepine systems and establish a practical entry to a previously underexplored fused heterocyclic scaffold.