Synthesis of quinazolinones CpCo()-catalyzed C-H functionalization of primary amides with oxadiazolones

Multi-heteroatom heterocycle synthesis through direct C-H bond activation is methodologically appealing but synthetically challenging. An efficient double C-N bond formation sequence to prepare quinazolinones utilizing primary amides and oxadiazolones in a catalytic redox-neutral [CoCp*(CO)I 2 ]/AgS...

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Published in:Organic & biomolecular chemistry 2023-04, Vol.21 (16), p.3335-3339
Main Authors: Wu, Xuan, Wu, Weiping, Fan, Shuaixin, Han, Xuanzhen, Wang, Zhixin, Xu, Hanxiao, Wang, Baochen, Zhu, Jin
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Summary:Multi-heteroatom heterocycle synthesis through direct C-H bond activation is methodologically appealing but synthetically challenging. An efficient double C-N bond formation sequence to prepare quinazolinones utilizing primary amides and oxadiazolones in a catalytic redox-neutral [CoCp*(CO)I 2 ]/AgSbF 6 system, where oxadiazolone could function as an internal oxidant to maintain the catalytic cycle, is reported. Amide-directed C-H bond activation and oxadiazolone decarboxylation are key to the success of this traceless, atom- and step-economic, and cascade approach for the construction of the quinazolinone skeleton. An efficient primary amide-directed C-H functionalization for the construction of quinazolinones was developed, where a double C-N bond was formed.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00387f