A One-Pot Synthesis of 2-Aminopyrimidines from Ketones, Arylacetylenes, and Guanidine

Abstract

The three-component reaction of ketones, arylacetylenes, and guanidine catalyzed by the KOBu/DMSO system leads to 2-aminopyrimidines in up to 80% yield. Depending on structure of the starting ketones, the aromatization of intermediate dihydropyrimidines occurs either with loss of hydrogen molecules or methylbenzenes. The latter process takes place in the ketones, in which one of the substituents is not a methyl group. The reaction conditions are tolerable for dialkyl-, aryl(hetaryl) alkyl-, and cycloalkyl ketones.

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3‐Ynones

“…We found that the condensation of ketones 1a – 1e with guanidine carbonate 2d or hydrochloride 2e under the same reaction conditions afforded 2‐aminopyrimidines 3q – 3u in good yields (Scheme ). These types of pyrimidines are especially important as these heterocycles have a broad range of biological activities such as anti‐inflammatory, analgesic, and antitubercular properties as well as adenosine receptor antagonist and protein kinase inhibitor abilities …”

Synthesis, Characterization, Molecular Docking, Acetylcholinesterase and α‐Glycosidase Inhibition Profiles of Nitrogen‐Based Novel Heterocyclic Compounds

“…Tris[2‐(2‐ or 4‐pyridyl)ethyl]phosphines were obtained by the procedure described in the literature [34] from phosphine and 2‐ or 4‐vinylpyridines in the super basic system KOH/DMSO (Scheme 3b). 2‐Aminopyrimidines 12 , 13 were synthesized via three‐component reaction of ketones (cyclohexanone for sample 12 and acetophenone for sample 13 ), phenylacetylene, and guanidine nitrate in one‐pot procedure (Scheme 3c) [35] …”

“…2-Aminopyrimidines 12, 13 were synthesized via three-component reaction of ketones (cyclohexanone for sample 12 and acetophenone for sample 13), phenylacetylene, and guanidine nitrate in one-pot procedure (Scheme 3c). [35]…”

Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K)

“…In the past decade, application of the superbasic reagents and catalysts has paved the route to conceptionally new acetylene-based syntheses of fundamental organic compounds. − Recently discovered C-vinylation of ketones with acetylenes catalyzed by superbase systems of MOH/DMSO or t BuOM/DMSO (M = Na, K) now serves as a springboard to trigger transition-metal-free one-pot cascade assemblies of such fundamental organic compounds as functionalized cyclopentenes, furans, , oxazoles, pyrazoles, , benzoxepine, pyrimidines, and analogs of natural pheromones . The number of syntheses based on this reaction is rapidly extending, but there are still topical issues related to the mechanistic features of these processes as well as to the special role of the above superbases.…”