Solvent-Free Synthesis and Antiviral Activity of Chiral Dialkyl 2-(Substituted-((4-(Pyridin-3-Yl)Pyrimidin-2-Yl)Amino)Methyl) Malonate

An efficient asymmetric synthesis of chiral β-amino acid ester derivatives containing a 4-(pyridin-3-yl)pyrimidin-2-yl amine moiety was developed. This catalytic asymmetric Mannich reaction gave target products in high yields (95%) and excellent enantioselectivities (>99% ee) using a cinchona-bas...

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Bibliographic Details
Published in:Journal of chemical research 2018-08, Vol.42 (8), p.428-433
Main Authors: Bai, Song, Liu, Shan, Zhu, Yunying, Lu, Jiali, Ai, Lina, Xue, Jing, Wu, Qin
Format: Article
Language:English
Subjects:
Catalysis
Solvents
Synthesis
Tobacco
Viruses
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Summary:An efficient asymmetric synthesis of chiral β-amino acid ester derivatives containing a 4-(pyridin-3-yl)pyrimidin-2-yl amine moiety was developed. This catalytic asymmetric Mannich reaction gave target products in high yields (95%) and excellent enantioselectivities (>99% ee) using a cinchona-based squaramide catalyst under solvent-free, one-pot conditions. Antiviral bioassays indicated that some of the chiral products exhibited higher antiviral activities against tobacco mosaic virus than the commercial compound ribavirin.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751918X15339142171145