Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 15, Pages 4131-4137Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00551k
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Funding
- National Natural Science Foundation of China [U2004189]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [20IRTSTHN005]
- Natural Science Foundation of Henan Province [212300410364]
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
- 111 Project [D17007]
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This paper presents an efficient method for the synthesis of 3-spirooxindole 3H-indoles through the coupling and spirocyclization of N-aryl amidines with diazo oxindoles. The mechanistic pathway involves a cascade process with easily accessible substrates, redox neutral conditions, high efficiency in forming multiple bonds, and attractive products in terms of structure and pharmaceutical properties.
In this paper, an efficient synthesis of 3-spirooxindole 3H-indoles through the coupling and spirocyclization of N-aryl amidines with diazo oxindoles is presented. Mechanistically, the formation of the title products involves a cascade process including Rh(iii)-catalyzed C(sp(2))-H bond cleavage, Rh-carbene formation and migratory insertion, intramolecular nucleophilic addition and ammonia elimination. In general, this novel spirocyclization features easily accessible substrates with a broad scope and generality, redox neutral reaction conditions, formation of multiple bonds with high efficiency, and structurally and pharmaceutically attractive products.
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