Duval Romain auteur aut IRD Lever J.R. auteur aut IRD text journalArticle eng text/pdf born digital access Naltrindole, naltrindole analogs and the benzofuran congener naltriben have been prepared by Fischer syntheses using mildly acidic, purely aqueous conditions. The preparation of naltrindole and several analogs was accomplished under almost neutral conditions using just the hydrochloride salts of naltrexone and various electron-rich and electron-poor phenylhydrazines in boiling water. The products were obtained by simple filtration in good to excellent yields and with high purities in the majority of cases. The route is suited to gram-scale synthesis, does not require the use of organic solvents, minimizes the use of corrosive acids, and is simple, efficient and environmentally friendly. Naltriben was prepared efficiently from the hydrochloride salts of naltrexone and O-phenylhydroxylamine but more forcing conditions, 6.0 N HCl, were required. A limitation to the method is the failure of Fischer cyclization between naltrexone and nitro-substituted phenylhydrazines under aqueous conditions. specialized 050MEDECI 020BIOCHI 12 2 304-309 2010 1463-9262 https://www.documentation.ird.fr/hor/fdi:010089848 10.1039/b920864j 1463-9262 https://www.documentation.ird.fr/hor/fdi:010089848 https://www.documentation.ird.fr/intranet/publi/2024-04/010089848.pdf Accès réservé (Intranet de l'IRD) IRD - Base Horizon / Pleins textes 2024-03-14 2024-04-25 fdi:010089848 fre