| Literature DB >> 31339318 |
Niklas Kraemer1, Clarabella J Li1, Jie S Zhu1, Julio M Larach1, Ka Yi Tsui1, Dean J Tantillo1, Makhluf J Haddadin2, Mark J Kurth1.
Abstract
The Davis-Beirut reaction provides access to <span class="Chemical">2H-indazoles from aromatic <class="Gene">span class="Chemical">nitro compounds. However, N-aryl targets have been traditionally challenging to access due to competitive alternate reaction pathways. Previously, the key nitroso imine intermediate was generated under alkaline conditions, but as reported here, the photochemistry of o-nitrobenzyl alcohols empowered Brønsted acid catalyzed conditions for accessing N-aryl targets. Anilines and alkyl amines give different outcomes under optimized conditions; the proposed mechanism was studied using quantum chemical calculations.Entities:
Mesh：
Substances：
Year: 2019 PMID： 31339318 PMCID： PMC6698363 DOI： 10.1021/acs.orglett.9b02213
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005