ChemInform Abstract: Synthesis of Ethyl Pyrimidine‐4‐carboxylates from Unsymmetrical Enamino Diketones and Their Application in the First Synthesis of Pyrimido[4,5‐d]pyridazin‐8(7H)‐ones

Rosa, Fernanda A.; Machado, Pablo; Fiss, Gabriela F.; Vargas, Pâmela S.; Fernandes, Tanize S.; Bonacorso, Hélio G.; Zanatta, Nilo; Martins, Marcos A. P.

doi:10.1002/chin.200913149

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β-Alkoxyvinyl-and β-Enamino α-Ketoesters1

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2022

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“…An interesting study revealed that their condensation with NCN binucleophiles, e.g. benzamidine, could occur at both competing carbonyl groups and, therefore, could result in the formation of pyrimidine-4-carboxylate 56 (the major or the only product in most cases) or pyrimidine-5-glyoxylate 57 (Table 7) [134]. The observed regioselectivity could be explained by the more electrophilic nature of the carbonyl group adjacent to the ester moiety as compared to the benzoyl-type fragment, with an exception of CF3-substituted ketone moiety.…”

Section: β-Alkoxyvinyl-and β-Enamino α-Ketoestersmentioning

confidence: 99%