Fused 1,4-Oxazepanes via Regioisomeric Enaminones: Practical Access to New Heterocyclic Scaffolds
Тип публікації :
Препринт
Дата випуску :
28 квітня 2026 р.
Автор(и) :
Oleksandr Kaliberda
Dmytro Leha
Vladyslav Peredrii
Kostiantyn Levchenko
Evgenij V. Zarudnitskii
Serhiy V. Ryabukhin
Dmytro M. Volochnyuk
eKNUTSHIR URL :
Журнал :
ChemRxiv
Цитування :
[APA 7] Oleksandr, K., Dmytro, L., Vladyslav, P., Kostiantyn, L., Evgenij, V. Z., Serhiy, V. R., & Dmytro, M. V. (2026). Fused 1,4-Oxazepanes via Regioisomeric Enaminones: Practical Access to New Heterocyclic Scaffolds. ChemRxiv,. https://doi.org/10.26434/chemrxiv.15002523/v1
[ДСТУ] Fused 1,4-Oxazepanes via Regioisomeric Enaminones: Practical Access to New Heterocyclic Scaffolds / K. Oleksandr та ін. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.15002523/v1 (дата звернення: 11.09.2026).
A practical synthetic platform based on regioisomeric enaminones derived from 1,4-oxazepan-6-one is described. Due to the presence of two nonequivalent methylene positions adjacent to the carbonyl group in the parent oxazepanone, the regioselectivity of enaminone formation was investigated. Although no fully regioselective protocol was identified, an efficient multigram-scale isolation method was developed, providing access to both complementary enaminone isomers as crystalline and storage-stable dielectrophilic intermediates. Their synthetic utility was demonstrated in annulation reactions with representative 1,2- and 1,3-binucleophiles. Hydrazine and hydroxylamine afforded fused pyrazole- and isoxazole-containing systems, whereas amidines, guanidine, and thiourea provided access to fused pyrimidine derivatives. Collectively, these results establish oxazepane-derived enaminones as a new class of practically accessible synthons for heterocyclic annulation chemistry and provide a modular route to previously underexplored fused 1,4-oxazepane-containing heterocyclic scaffolds.