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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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
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Language:English
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cited_by cdi_FETCH-LOGICAL-a310t-84df218ce75d553fdeb052820a17a2b3da272d40b3098047fa573dfa4af571a83
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container_issue 17
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container_title Journal of organic chemistry
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creator Ding, Yuxin
Kuang, Jinqiang
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description 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.
doi_str_mv 10.1021/acs.joc.1c01602
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title Environmentally Benign Synthesis of Quinoline–Spiroquinazolinones by Iron-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of Secondary/Tertiary Anilines and 4‑Methylene-quinazolinones
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