Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 9, Pages 6458-6466Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00303
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Funding
- Sci-Tech Development Project of Jilin Province in China [20200801039GH]
- Chunhui Plan Cooperative Research Project of the Ministry of Education of China
- Foundation of Jilin Educational Committee [JJKH20211225KJ, JJKH20211229KJ]
- Outstanding Young Teacher Training Program of Jilin University
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This method describes a one-pot synthetic approach for the construction of indole/pyrrole-fused 1,4-diazepanone scaffolds, utilizing readily available starting materials and exhibiting good stereoselectivity. It is valuable for the gram-scale synthesis of highly substituted fused heterocycles containing the 1,4-diazepanone moiety.
A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This method involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita-Baylis-Hillman-derived allylamines. The readily available starting materials, good stereoselectivity, and gram-scale synthesis make this method valuable for the construction of highly substituted fused heterocycles containing the 1,4-diazepanone moiety.
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