Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 17, Pages 4583-4590Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00851c
Keywords
-
Categories
Funding
- National Natural Science Foundation of China [U2004189]
- Project of Central Plains Science and Technology Innovation Leading Talents [224200510009]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [20IRTSTHN005]
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
- Australian Research Council [DE210100053]
- UOW RITA Grant 2021
- UOW
- Australian Research Council [DE210100053] Funding Source: Australian Research Council
Ask authors/readers for more resources
This study presents a coupling partner-dependent unsymmetrical C-H bond functionalization of N-phenoxyacetamides, leading to the formation of sophisticated spirocyclic scaffolds. The reactions with diazopyrazolones and diazooxindoles result in the formation of spiropyrazolonyl indazoles and bispirooxindoyl dihydrobenzofurans, respectively. These transformations provide effective strategies for the synthesis of spiroheterocyclic skeletons and demonstrate unprecedented reaction modes of N-phenoxyacetamides with cyclic diazo compounds.
A coupling partner-dependent unsymmetrical C-H bond functionalization of N-phenoxyacetamides leading to the formation of sophisticated spirocyclic scaffolds is presented herein. To be specific, spiropyrazolonyl indazoles were formed from N-phenoxyacetamides and diazopyrazolones through sequential C-H bond cleavage and carbene insertion into two different phenyl moieties. On the other hand, bispirooxindoyl dihydrobenzofurans were formed from N-phenoxyacetamides and diazooxindoles through C-H bond cleavage and cascade carbene insertion into phenyl and oxindoyl moieties, respectively. These transformations not only provided effective strategies for the synthesis of the otherwise difficult-to-obtain spiroheterocyclic skeletons from simple and readily available substrates in a straightforward and atom-economic manner, but also disclosed some unprecedented reaction modes of N-phenoxyacetamides with cyclic diazo compounds. Structural elaborations of the products obtained herein furnished some valuable heptacyclic architectures. Mechanistic experiments and DFT calculations were also carried out to unveil the reaction mechanisms, especially the origin of the excellent chemoselectivity and diastereoselectivity demonstrated in the formation of bispirooxindoyl dihydrobenzofuran products.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available