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

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 presenc...

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Published inJournal of organic chemistry Vol. 87; no. 14; pp. 9414 - 9418
Main Authors Babu, Sakamuri Sarath, Gopinath, Purushothaman
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHLORIDES
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00832