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Paper | Regular issue | Vol 96, No. 4, 2018, pp.716-732
Published online, 19th March, 2018
DOI: 10.3987/COM-18-13880
Nucleophilic Aroylation on Fluoroquinazolines Catalyzed by N-Heterocyclic Carbenes

Masashi Tachikawa, Mizuki Nakagawa, and Yumiko Suzuki*

*Department of Materials and Life Science, Faculty of Science and Technology, Sophia University, Kioi-cho 7-1, Chiyoda-ku, Tokyo 102-8554, Japan

Abstract

We report on the synthesis of 7-benzoyl- and 7-heteroaroylquinazolines from 7-fluoroquinazolines and aromatic aldehydes by N-heterocyclic carbene (NHC)-catalyzed nucleophilic aromatic substitution, showing that the NHC derived from 1,3-dimethylimidazolium iodide outperformed those originating from other azolium (e.g., thiazolium and triazolium) salts. Additionally, the developed methodology allowed the preparation of 5- and 8-aroylquinazolines from the corresponding fluoroquinazolines.