P. C. Iuhas, F. Georgescu, E. Georgescu
2001
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0
Influential Citations
3
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Journal
Revue Roumaine De Chimie
Abstract
New furyl-substituted and new thienyl-substituted pyrrolo[1,2-c]pyrhfidine compounds are obtained by [3 + 2] dipolar cycloaddition reactions of 4-(2-furyl)- and 4-(2-thienyl)pyrimidinium ylides to ethyl propiolate. The NMR and IR spectra confirm the structures assigned to the new compounds. For the first time in the pyrimidine series, perturbation and frontier orbital theories were applied to explain the regioselectivity in the [3 + 2] dipolar cycloaddition of 4-(2-furyl)- and 4-(2-thienyl)pyrimidinium ylides to ethyl propiolate. Molecular orbital calculations were carried out by AM1 method.