N-Heterocyclic carbene-catalyzed monoacylation of 1,4-naphthoquinones with aldehydes.
The NHC-catalyzed conjugate hydroacylation of 1,4-naphthoquinones allows for the synthesis of monoacylated 1,4-dihydroxynaphthalene derivatives. These targets, difficult to prepare selectively by standard protocols, represent important intermediates in the elaboration of highly substituted 1,4-naphthoquinone derivatives, which constitute relevant pharmaceutical scaffolds. High regioselectivity has been observed in the hydroacylation reaction when starting from nonsymmetrical quinones.
Molina
María Teresa
MT
Instituto de Química Médica (CSIC), C/Juan de la Cierva, 3, 28006-Madrid, Spain.
Navarro
Cristina
C
Moreno
Ana
A
Csákÿ
Aurelio G
AG
D000215:Acylation; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*
D000447:Aldehydes; D006571:Heterocyclic Compounds; D006873:Hydroquinones; D009285:Naphthoquinones; C030011:carbene; C063601:1,4-naphthohydroquinone; D008697:Methane; C035342:1,4-naphthoquinone