One-Pot and Metal-Free Synthesis of 3-Arylated 4-Nitrophenols via Polyfunctionalized Cyclohexanones from β-Nitrostyrenes

  1. Haruyasu AsaharaORCID Logo,
  2. Minami Hiraishi and
  3. Nagatoshi NishiwakiORCID Logo

Submitting author affiliation: Kochi University of Technology, Kami, Japan

Beilstein Arch. 2020, 202063. doi:10.3762/bxiv.2020.63.v1

Published 22 May 2020

  • Preprint

Abstract

β-Nitrostyrenes underwent the Diels-Alder reaction with Danishefsky’s diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated 5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated 4-nitrophenols. The reaction of nitrostyrenes with Danishefsky’s diene could be conducted in one-pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group such as a thienyl group could be introduced into the nitrophenol framework.

Keywords: Diels-Alder reaction; Danishefsky’s diene; Nitroalkene; 3-Arylated 4-nitrophenol; Polysubstituted cyclohexanone

Supporting Information

Format: DOCX Size: 5.4 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available in the Beilstein Journals, 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:

Asahara, H.; Hiraishi, M.; Nishiwaki, N. Beilstein Arch. 2020, 202063. doi:10.3762/bxiv.2020.63.v1

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

© 2020 Asahara et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia