Photomediated Tandem Sulfonyl Addition-Chemoselective N-Cyclization of o -Alkenyl Aryl Ureas: Direct Assembly of Functionalized Dihydroquinazolinones.

Autor: Babu SS; Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517507, India., Gopinath P; Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517507, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Jul 15; Vol. 87 (14), pp. 9414-9418. Date of Electronic Publication: 2022 Jul 06.
DOI: 10.1021/acs.joc.2c00832
Abstrakt: Photoredox-mediated tandem addition-chemoselective cyclization of o -alkenyl aryl ureas is reported for the synthesis of sulfonyl and activated alkyl-decorated dihydroquinazolinones. By a careful choice of o -alkenyl aryl urea starting materials, we achieved chemoselective N-cyclization in the presence of more reactive amidic oxygen. We have demonstrated the scope of the methodology with a variety of sulfonyl chlorides and activated alkyl halides. Finally, large-scale synthesis of sulfonyl-substituted dihydroquinazolinone showcases the synthetic utility of the methodology.
Databáze: MEDLINE