5-(3,4-Dimethoxybenzyl)-2,4-pyrimidinediamine hydrochloride (1:1)
CAS Number:
2507-23-5
Molecular Formula:
C13H17ClN4O2
Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones
Literature Information
Publication Date
2019-05-09
DOI
10.1039/C9QO00357F
Impact Factor
5.281
Authors
Xiao-Rui Ren, Jun-Bing Lin, Xiu-Qin Hu, Peng-Fei Xu
View Original
Abstract
An enantioselective inverse-electron-demand aza-Diels–Alder reaction of saccharin-derived 1-azadienes and azlactones was developed using a phenylalanine-derived bifunctional Brønsted base-squaramide catalyst, which furnished the chiral tricyclic architectures bearing a quaternary amino acid moiety in high yields with moderate to excellent selectivities. A gram-scale synthesis and further elaboration of the product were also conducted to further demonstrate the synthetic utility of the reaction.
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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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6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine
CAS Number:
1203499-17-5
Molecular Formula:
C7H7BrN2O
1-(3-Bromo-4-fluorophenyl)methanamine hydrochloride (1:1)
CAS Number:
202865-68-7
Molecular Formula:
C7H8BrClFN
![2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide structure](https://static.chemtradehub.com/structs/137/1370261-96-3-40df.webp "2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide structure")
2-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-{[3-(2H-1,2,3-triazol-2-yl)phenyl]amino}-5-pyrimidinecarboxamide
CAS Number:
1370261-96-3
Molecular Formula:
C19H23N9O
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