N-(4-Chlorobenzyl)-beta-alanine hydrochloride (1:1)
CAS Number:
1172479-10-5
Molecular Formula:
C10H13Cl2NO2
An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks
Literature Information
Publication Date
2023-12-12
DOI
10.1039/D3QO01184D
Impact Factor
5.281
Authors
Meng Wang, Ze-Hong Zheng, Mu-Qiu Chen, Gu Zhan, Jie Wang, Qian-Qian Yang, Wei Huang
View Original
Abstract
A series of tetrahydro-β-carbolin 1,3-diketone frameworks can be synthesized under mild conditions utilizing azlactones and indole-2-ylamides. This highly efficient [4 + 2] annulation further broadens the application of azlactones derived from amino acids via the umpolung strategy in organic synthesis, featuring good compatibility. Furthermore, control experiments indicate that the addition of the oxidant DDQ could complete the homocoupling of azlactones without a metal mediator. Moreover, DFT computational calculations were performed to further elucidate the chemoselectivity of the reaction and a plausible mechanism is proposed to explain the reaction process.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Molecular Formula:
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