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. https://doi.org/10.3762/bxiv.2022.75.v1

Published 22 Sep 2022

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This preprint has not been peer-reviewed.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

Abstract

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

Supporting Information

Format: PDF Size: 6.8 MB   Download

How to Cite

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

Download citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2022 Kotha et al.; licensee Beilstein-Institut.
This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

OTHER BEILSTEIN-INSTITUT OPEN SCIENCE ACTIVITIES