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Multigram Synthesis of Heterabicyclo[4.1.1]octanes: Conformationally Restricted Azepane Analogs for Drug Discovery

Year: 2026
Type: preprint
Abstract: A convenient and scalable synthetic approach enabling multigram access to three heterabicyclo[4.1.1]octane families – 2-azabicyclo[4.1.1]octane, 2,5-diazabicyclo[4.1.1]octane, and 2-oxa-5-azabicyclo[4.1.1]octane – is described. Starting f rom readily available cis -1,3-disubstituted cyclobutanes, the target scaf folds were obtained by the common lactamization – amide reduction strategy, providing access to the (mono)protected (di)amines as ready-to-use building blocks. Representative members were characterized by single-crystal X-ray diffraction studies, and basicity (p K a ) and lipophilicity (Log P ) were determined for selected compounds. These rigid f rameworks can be considered as saturated analogs of the azepane, 1,4-diazepane, and 1,4-oxazepane rings.
Source: ChemRxiv
DOI: 10.26434/chemrxiv.15008479/v1
Authors: Ivan V. Mazurenko, Yevhen M. Ivon, Nataliia Y. Slyvka, Olena D. Semoshkina, Oleksandr S. Liashuk, Dmytro Lesyk, Petro Borysko, Viktor Yakubovskyi, Svetlana V. Shishkina, Oleksandr O. Grygorenko
Institutions: Lesya Ukrainka Volyn National University, Enamine (Ukraine), Taras Shevchenko National University of Kyiv, National Academy of Sciences of Ukraine, Institute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar, Institute of Organic Chemistry
Language: English
Field: Chemistry
Open Access status: green
OpenAlex ID: W7211971225
Cites: 37
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Related to: 10