Environmentally Benign Synthesis of Quinoline–Spiroquinazolinones by Iron-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of Secondary/Tertiary Anilines and 4‑Methylene-quinazolinones

We report an efficient iron-catalyzed cross-dehydrogenative coupling [4 + 2] annulation of secondary/tertiary anilines with quinazolinones to generate quinoline–spiroquinzolinones. The reaction proceeds smoothly with a relatively broad variety of functional groups, a cheap transition metal catalyst...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-09, Vol.86 (17), p.12257-12266
Main Authors: Ding, Yuxin, Kuang, Jinqiang, Xiao, Xuqiong, Wang, Lei, Ma, Yongmin
Format: Article
Language:English
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Summary:We report an efficient iron-catalyzed cross-dehydrogenative coupling [4 + 2] annulation of secondary/tertiary anilines with quinazolinones to generate quinoline–spiroquinzolinones. The reaction proceeds smoothly with a relatively broad variety of functional groups, a cheap transition metal catalyst (FeCl3), and environmentally friendly oxidant (H2O2/O2) under mild reaction conditions. Creatively, N-methylanilines are employed for the first time for the cycloaddition as both methyl and methylene sources attached to the N atom of tetrahydroquinolines.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01602