G. Coppola, M. Shapiro
May 1, 1981
Citations
0
Influential Citations
9
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
N,N'-Dimethylthiourea and 3,4,5,6-tetrahydro-2-pyrimidinethiol were allowed to react with 2-chloro-nicotinonitrile (1) and their products investigated by standard methods and by carbon-13 nmr. In both instances, displacement of the chlorine occurred by nitrogen not the sulfur of the thioureas. Secondary cyclizations occurred by attack of nitrogen on the nitrile to furnish 3a, and by sulfur on the nitrile to give 4b, a new ring system. Tricyclic 4b was hydrolyzed in dilute acid to give 5, or alkylated with methyl iodide in the presence of sodium hydride to give the ring opened product 6.