Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles |
| |
| Authors: | Olga V. Petrova Arsalan B. Budaev Elena F. Sagitova Igor A. Ushakov Lyubov N. Sobenina Andrey V. Ivanov Boris A. Trofimov |
| |
| Affiliation: | A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia; (O.V.P.); (A.B.B.); (E.F.S.); (I.A.U.); (L.N.S.); (A.V.I.) |
| |
| Abstract: | An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed. |
| |
| Keywords: | acylethynylpyrroles guanidine cyclocondensation aminopyrimidine |
|
