Sintese e atividade catalitica de biguanidinas

AUTOR(ES)
DATA DE PUBLICAÇÃO

1997

RESUMO

Biguanides are organic bases that have risen attention after the discovery of the antimalarial activity of Paludrine (1-p-chlorophenil-5-isopropylbiguanide). The most used synthesis route is from substituted dicyandiamide; however, these compounds are not commercially availabe. In this work a new synthetic route starting with carbodiimides to produce two biguanides still not described in the literature is given: 1-isopropyl-2,5-diisopropylamine-1,3,4-triazole (C11H23N5) and 1,2,3,4,5-pentacyclohexylbiguanide (C32H57N5), know as ISOBG and PCBG, respectively. ISOBG was prepared by the addition reaction of hydrazine hydrate to diisopropylcarbodiimide; PCBG was prepared by the reaction of 1,3,5-tricyclohexylguanidine (TCG) and dicyclohexylcarbodiimide. The catalytic activity of new biguanides was studied from the transesterification reaction of soybean oil with methanol and from the condensation of benzaldehyde and acetone, and compared to the results obtained with TCG. At 1 mol% of PCBG, 86% of methyl esters are obtained while TCG gives 76% and ISOBG, under the same conditions, does not show any activity. The activity of PCBG was further studied for the condensation of benzaldehyde and acetone. IN the presence of 10 mol% of PCBG, 91% of benzalacetone is obtained, while TCG gives 74%.

ASSUNTO(S)

inorganica

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