![5'-Fluoro-[2,3'-biindolinylidene]-2',3-dione structure](https://static.chemtradehub.com/structs/251/251903-00-1-9cb1.webp "5'-Fluoro-[2,3'-biindolinylidene]-2',3-dione structure")
Generation and application of carbodiimide anions: efficient construction of 2-aminopyrimidines via a cascade [4 + 2] annulation/aromatization sequence
Literature Information
Publication Date
2023-10-11
DOI
10.1039/D3QO01604H
Impact Factor
5.281
Authors
Chuan-Chuan Wang, Xin-Lu Wang, Qing-Long Wang, Yi-Zhi Gong, Xue-Hui Hou, Jun-Tao Liu, Ya-Jing Chen
View Original
Abstract
The cascade [4 + 2] annulation/aromatization reactions between carbodiimide anions and α,β-unsaturated imines are developed. This is the first report on regulating N-Ts cyanamides to participate in reactions absolutely via carbodiimide anions rather than previously reported cyanamide anions, affording a convenient method for synthesizing 2-aminopyrimidines. More importantly, this work expands the application of carbodiimides, broadening the coupling substrate scope to electrophilic partners and providing new strategies to construct six-membered N-heteroaromatic scaffolds. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.
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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
Recommended Compounds
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1265341-14-7
Molecular Formula:
C12H11F2NO2
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1-Isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline
CAS Number:
175975-76-5
Molecular Formula:
C16H22N2O
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