2021
DOI: 10.18257/raccefyn.1465
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Uso de una mezcla dioxane/MeOH/NaBH4 en caliente como un medio conveniente para la reducción química selectiva del doble enlace C=C en sistemas α,β-insaturados

Abstract: Productos de Knoevenagel diversamente sustituidos fueron sometidos a reducción con una solución de NaBH4 en MeOH/p-dioxano a 70 oC. A través de este proceso, se alcanzó la reducción selectiva de sus dobles enlaces C=C en todos los casos. Las condiciones de reducción establecidas toleró una variedad de grupos funcionales, aunque productos simples de condensación aldólica o de Claisen- Schmidt mostraron menos selectividad hacia la reducción del doble enlace C=C, y por el contrario, condujo específicamente a la r… Show more

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“…Subsequently, the Knoevenagel condensation of compounds 20 with o-bromo-benzaldehyde afforded the corresponding arylidene-derivatives 21 a-i in 81-95 % yield, (step 3, Scheme 2). Finally, the selective reduction of the α,β-unsaturated moiety of 21 a-i mediated by NaBH 4 in a warm MeOH/p-dioxane mixture, [9] provided the expected radical precursors 17 a-i in 70-93 % yield, (step 4, Scheme 2). Reduction was performed because, in principle, the true configuration of the α,β-C=C double bond in 21 was unknown and because the major proximity between the bromophenyl moiety and the cyano function was required for the subsequent radical-mediated domino reaction, as shown in (entry 4, Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…Subsequently, the Knoevenagel condensation of compounds 20 with o-bromo-benzaldehyde afforded the corresponding arylidene-derivatives 21 a-i in 81-95 % yield, (step 3, Scheme 2). Finally, the selective reduction of the α,β-unsaturated moiety of 21 a-i mediated by NaBH 4 in a warm MeOH/p-dioxane mixture, [9] provided the expected radical precursors 17 a-i in 70-93 % yield, (step 4, Scheme 2). Reduction was performed because, in principle, the true configuration of the α,β-C=C double bond in 21 was unknown and because the major proximity between the bromophenyl moiety and the cyano function was required for the subsequent radical-mediated domino reaction, as shown in (entry 4, Scheme 1).…”
Section: Resultsmentioning
confidence: 99%