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Deacylative alkylation (DaA) of N-methyl-3-acetyl-2-oxindole for the synthesis of symmetrically 3,3-disubstituted 2-oxindoles. An access gate to anticancer agents and natural products. Anais da ABC (AABC)
MORENO-CABRERIZO,CRISTINA; ORTEGA-MARTÍNEZ,AITOR; MOLINA,CYNTHIA; NÁJERA,CARMEN; SANSANO,JOSÉ M..
ABSTRACT The synthesis of 3,3-disubstituted N-methyloxindoles, starting from 3-acetyl-2-hydroxy-1-methyloxindole employing a sequential one-pot synthesis, is studied. The process involves a first alkylation in the presence of 1 equiv. of both organic halide and Triton B and the second one employs another 1.5 equiv. of each in moderate to high yields. This procedure is compared with the results obtained from the direct dialkylation of N-methyloxindole. The metathesis of one of the corresponding diallylated product was also studied obtaining the spiranic oxindole. All these methodologies are directed towards the access to anticancer agents and natural biologically active products.
Tipo: Info:eu-repo/semantics/article Palavras-chave: Deacylation; Alkylation; 2-oxindoles; Metathesis; Anticancer; Natural products.
Ano: 2018 URL: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652018000301089
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Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs Anais da ABC (AABC)
GARCIA-MUÑOZ,MARÍA JESÚS; SIRVENT,ANA; FOUBELO,FRANCISCO; YUS,MIGUEL.
ABSTRACT A simple methodology for the synthesis of enynes by indium mediated diastereoselective allylation of aromatic N-tert-butanesulfinylimines bearing alkenyl groups at ortho-position with allyl bromide has been developed. The addition of the allyl indium intermediate to the chiral imine took place with excellent diastereoselectivity. Ruthenium-catalyzed ring-closing metathesis of the resulting enynes provided the expected cyclic 1,3-dienes in good to moderate yields. These chiral dienes are potential precursors of biologically and pharmacologically active morphane derivatives.
Tipo: Info:eu-repo/semantics/article Palavras-chave: Allylation; Imines; Dienes; Enynes; Metathesis; Alkaloids.
Ano: 2018 URL: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652018000301059
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