Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 7, Pages 4590-4602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02919
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Funding
- Fundacao de Amparo a Pesquisa do Estado do Rio Grande do Sul (FAPERGS)
- FAPERGS/CNPq [16/2551-0000477-3]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [407898/2018-2]
- Deutscher Akademischer Austauschdienst (DAAD) [57507869, 91793237]
- Coordenacao de Aperfeicoa-mento de Pessoal de Nivel Superior (CAPES)
- FAPERGS
- CNPq
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Selective N- or O-alkylation of 4-(trihalomethyl)-pyrimidin-2(1H)-ones using 5-bromo enones/enaminones as alkylating agents is reported. The selectivity towards the N- or O-regioisomer is determined by the substituent at the 6-position of the pyrimidine ring, allowing the preparation of each isomer as the sole product in yields of 60-95%. Subsequent cyclocondensation of the enaminone moiety with nitrogen dinucleophiles leads to pyrimidine-azole conjugates with yields of 55-83%.
The selectiveN-orO-alkylation of 4-(trihalomethyl)-pyrimidin-2(1H)-ones, using 5-bromo enones/enaminones as alkylat-ing agents, is reported. It was found that the selectivity toward theN-orO-regioisomer is driven by the substituent present at the 6-positionof the pyrimidine ring, thus enabling the preparation of each isomeras the sole product, in 60-95% yields. Subsequent cyclocondensationof the enaminone moiety with nitrogen dinucleophiles led topyrimidine-azole conjugates in 55-83% yields.
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