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

Tatjana Gazivoda; Silvana Raić-Malić; Antonija Hergold-Brundić; Mario Cetina

doi:10.3390/molecules13112786

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

Molecules. 2008 Nov 6;13(11):2786-95. doi: 10.3390/molecules13112786.

Authors

Tatjana Gazivoda¹, Silvana Raić-Malić, Antonija Hergold-Brundić, Mario Cetina

Affiliation

¹ Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Zagreb, Croatia.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

Pyrimidines
alpha-(1-carbamyliminomethylene)-gamma-butyrolactone
4-Butyrolactone