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

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 s...

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Bibliographic Details
Published in:ACS omega 2018-10, Vol.3 (10), p.14258-14265
Main Authors: Sawant, Rajiv T, Stevens, Marc Y, Odell, Luke R
Format: Article
Language:English
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Summary: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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.8b02298