Reação de alfa -amidoalquilação de ions N-aciliminio com nucleofilos de carbono em sistema micelar SDS/agua, na ausencia de solvente e em liquido ionico : aplicação na sintese de um analogo da febrifugina / alfa -amidoalkylation of N-acyliminium ions with carbon nucleophiles in SDS/water, under solvent-free condition and in ionic liquid. Aplication to the synthesis of a febrifugine analog

AUTOR(ES)

Nilton Soares Camilo

DATA DE PUBLICAÇÃO

2006

RESUMO

Our work involved the formation of N-acyliminium ions, generated under the following reaction conditions: SDS/water micelles, solvent-free and in ionic liquido N-acyliminium ions were generated from the corresponding carbamates (N-Boc-2-methoxypyrrolidine and N-Boc-2-methoxypiperidine) with the aid of a Lewis or Bronsted acid catalyst. Both aqueous HCI and InCl3 in catalytic amounts were used in the reactions carried out in SDS/water system. The yields obtained in the a-amidoalkylations with silyl enol ethers in this way were moderate. However, good yield were achieved using 1,3-dicarbonyl compounds and N-Boc-2-methoxypirrolidine in the presence of catalytic InCl3. In the neat condition, good yields with silyl enol ethers and 1,3-dicarbonyl compounds as nucleophiles were achieved in the a-amidoalkylation reaction with catalytic InCl3. In the reactions involving the ionic liquid BMI.InCI4, good yields were observed with the use of activated olefins. As an application of the study, the synthesis of a febrifugine analogout arming to improve its antimalarial activity.

ASSUNTO(S)

sistema micelar solvent-free liquido ionico micelles ausencia de solvente n-acyliminium ion ionic liquid ions n-aciliminio

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