Design and Synthesis of Nitro Containing Cage Heterocycles as High-Density Materials Derived from Pentacycloundecane (PCUD) Systems

Submitting author affiliation:
Indian Institute of Technology-Bombay, Powai, Mumbai, India

Beilstein Arch. 2022, 202275.

Published 22 Sep 2022

This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


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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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Kotha, S.; Salman, M.; Cheekatla, S. R.; Ansari, S. Beilstein Arch. 2022, 202275. doi:10.3762/bxiv.2022.75.v1

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