Synthesis and structural characterization of the 5-(2-haloethyl)pyrimidines--hydrogen-bonded chains in alpha-(1-carbamyliminomethylene)-gamma-butyrolactone

Three novel 5-(2-haloethyl)pyrimidine derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, MS, IR spectra and elemental analysis. Iodine and chlorine atoms in the C-5 side chain were introduced by reaction of 5-(2-hydroxyethyl)pyrimidine with hydroiodic acid and phosphoryl chloride, re...

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Published inMolecules (Basel, Switzerland) Vol. 13; no. 11; pp. 2786 - 2795
Main Authors Gazivoda, Tatjana, Raić-Malić, Silvana, Hergold-Brundić, Antonija, Cetina, Mario
Format Journal Article
LanguageEnglish
Published Switzerland MDPI 06.11.2008
Subjects
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Crystallography, X-Ray
Hydrogen Bonding
Molecular Structure
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Spectrum Analysis
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Summary:Three novel 5-(2-haloethyl)pyrimidine derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, MS, IR spectra and elemental analysis. Iodine and chlorine atoms in the C-5 side chain were introduced by reaction of 5-(2-hydroxyethyl)pyrimidine with hydroiodic acid and phosphoryl chloride, respectively. The structure of the intermediate alpha-(1-carbamyliminomethylene)-gamma-butyrolactone was determined by X-ray crystal structure analysis. The molecule deviates very slightly from planarity. Three N-H...O hydrogen bonds link the molecules into one-dimensional chains of edge-fused rings.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules13112786