N -Alkylation of 4-Trichloromethylpyrimidinones: Synthesis of Some New and Interesting Modified Nucleoside Analogues

Nilo Zanatta, Patrícia B. Brondani, Simone S. Amaral, Taritza D. Oliveira, Helio G. Bonacorso and Marcos A.P. MartinsNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil. AbstractThe N1-alkylation of 4-(trichl...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry insights 2009-12, Vol.2009 (2), p.7-14
Main Authors: Zanatta, Nilo, Brondani, Patricia B, Amaral, Simone S, Oliveira, Taritza D, Bonacorso, Helio G, Ma
Format: Article
Language:English
Subjects:
Alkylating agents
Alkylation
Analysis
Chemical properties
High performance liquid chromatography
Methods
Nuclear magnetic resonance spectroscopy
Nucleoside analogs
Production processes
Pyrimidines
Spectra
Thin layer chromatography
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Nilo Zanatta, Patrícia B. Brondani, Simone S. Amaral, Taritza D. Oliveira, Helio G. Bonacorso and Marcos A.P. MartinsNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil. AbstractThe N1-alkylation of 4-(trichloromethyl)pyrimidin-2(1H)-one, 4-methoxy-4-(trichloromethyl)-3,4-dihydropyrimidin- 2(1H)-one, and 5-bromo-4-methoxy-4-(trichloromethyl)-3,4-dihydropyrimidin-2(1H)-one with selected alkylating agents such as 2-chloroacetamide, diethyl 2-bromomalonate, and 5-bromo-1,1,1-trichloro-4-methoxypent-3-en-2-one, is presented. Further reactions of 1-[5,5,5-trichloro-2-methoxy-4-oxo-penten-2-yl]4-trichloromethyl-pyrimidin-2(1H)-one with primary amines and aminoalcohols furnished a series of unexpected new acyclic nucleoside analogues.
ISSN:1178-6396
1178-6396
DOI:10.4137/OCI.S3690