Beilstein Arch. 2026, 202637. https://doi.org/10.3762/bxiv.2026.37.v1
Published 14 Oct 2026
Fused nitrogen-containing heterocycles with seven or more atoms form the structural scaffold of many natural and synthetic molecules possessing diverse range of biological activity. A series of new fused azepanes and azonanes have been prepared via two sequential Hofmann-type cleavages of the endocyclic C–N bonds in azetidinium rings of decahydro-1H,6H-biscyclopenta[2,3]azeto[1,2-a:2’1’-e]pyrrolium system. The latter resulted from double intramolecular alkylation of pyrrolidine nitrogen in (1R(S),5R(S),7R(S),8R(S))-6-azadispiro[4.1.4.2]tridecane-1,8-diyldimethanol (7), which easily occurs under Appel reaction conditions. A simple 7-step synthesis of 7 from 1-chloronon-8-en-4-one and unsubstituted hydroxylamine via intramolecular 1,3-dipolar cycloaddition in α-pent-4-en-1-yl nitrones of pyrroline series was described earlier.
Keywords: azepanes; azonanes; Hofmann elimination; quaternary azetidinium salts; ring expansion
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Khoroshunova, Y. V.; Dobrynin, S. A.; Rybalova, T. V.; Kirilyuk, I. A. Beilstein Arch. 2026, 202637. doi:10.3762/bxiv.2026.37.v1
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