Microwave-Assisted aza-Friedel-Crafts Arylation of N-Acyliminium Ions: Expedient Access to 4-Aryl 3,4-Dihydroquinazolinones

Rajiv T Sawant; Marc Y Stevens; Luke R Odell

doi:10.1021/acsomega.8b02298

Microwave-Assisted aza-Friedel-Crafts Arylation of N-Acyliminium Ions: Expedient Access to 4-Aryl 3,4-Dihydroquinazolinones

ACS Omega. 2018 Oct 29;3(10):14258-14265. doi: 10.1021/acsomega.8b02298. eCollection 2018 Oct 31.

Authors

Rajiv T Sawant¹, Marc Y Stevens¹, Luke R Odell¹

Affiliation

¹ Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden.

Abstract

A one-pot microwave-assisted aza-Friedel-Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A solvent-directed process for the selective aza-Friedel-Crafts arylation of electron-rich aryl/heteroaryl/butenyl-tethered N-acyliminium ions is also described.