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

The three-component reaction of ketones, arylacetylenes, and guanidine catalyzed by the KOBu t /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 molecul...

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Veröffentlicht in:Journal of organic chemistry 2017-01, Vol.82 (1), p.119-125
Hauptverfasser: Schmidt, Elena Yu, Tatarinova, Inna V, Protsuk, Nadezhda I, Ushakov, Igor’ A, Trofimov, Boris A
Format: Artikel
Sprache:eng
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Zusammenfassung:The three-component reaction of ketones, arylacetylenes, and guanidine catalyzed by the KOBu t /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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02233