Beilstein Arch. 2022, 202275. https://doi.org/10.3762/bxiv.2022.75.v1
Published 22 Sep 2022
A variety of pentacycloundecane (PCUD) based cage compounds containing nitro groups were synthesized via a simple synthetic method starting with cage diones. Eight PCUDs were used for nitro functionalization. These cage diones were prepared starting with easily accessible starting materials such as 2,3-dimethylhydroquinone, 1,4-dihydroxybenzene, and cyclopentadiene. Here, we have used Diels–Alder (DA) reaction, [2+2] photocycloaddition, and Henry reaction as key steps. Transannular cyclization plays an important role to generate a nitro substituted cage heterocycles via base promoted reaction using nitromethane as a reagent. Some of these oxa-cage structures have been further supported by single-crystal X-ray diffraction studies.
Keywords: Diels–Alder reaction, photocycloaddition, Henry reaction, transannular cyclization, heterocycles, nitro compounds, cage diones, PCUD, and oxa-cages
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Kotha, S.; Salman, M.; Cheekatla, S. R.; Ansari, S. Beilstein Arch. 2022, 202275. doi:10.3762/bxiv.2022.75.v1
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