Pyrrole-Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
Olga V Petrova1, Arsalan B Budaev1, Elena F Sagitova1
1A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia.
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.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Cycloaddition Reactions: Overview
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Cycloaddition Reactions: MO Requirements for Thermal Activation
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...


