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U ovom radu opisana je sinteza novih 1,2,3-triazolom premoštenih arilimidamidnih derivata benzimidazola, poznatih i kao reverzni amidini benzimidazola, s potencijalnim antitripanosomskim djelovanjem. Za pripravu ciljanih spojeva korištene su klasične metode organske sinteze. Arilimidamidni derivati benzimidazola (23a–23c, 24a–24c, 25a–25c) pripravljeni su iz odgovarajućih 5(6)-aminobenzimidazolnih prekursora (20a–20c, 21a–21c, 22a–22c) i priređenog S-(2-naftilmetil)tiobenzimidatnog hidrobromida 4. 5(6)-aminobenzimidazolni prekursori dobiveni su reakcijom redukcije iz 5(6)-nitrobenzimidazolnih prekursora (17a–17c, 18a–18c, 19a–19c) pripravljenih kondenzacijom bisulfitnih adukata benzaldehidnih prekursora (13a–13c, 14a–14c, 15a–15c) s 4-nitro-o-fenilendiaminom 16. Benzil- (13a–13c), pikolil- (14a–14c) i etinilmorfolin- (15a–15c) 1,2,3-triazolni derivati benzaldehida pripravljeni su regioselektivnom Cu(I)-kataliziranom cikloadicijom iz priređenih 4-(prop-2-iniloksi)benzaldehida (6a–6c) i odgovarajućih azida. Strukturna i spektroskopska karakterizacija novopripravljenih spojeva provedena je 1H i 13C NMR spektroskopijom. In this work the synthesis of new 1,2,3-triazolyl bridged arylimidazole benzimidazole derivatives, also known as benzimidazole reversed amidines with potential antitrypanosomal activity is described. For the synthesis of target compounds classical methods of organic sythesis were used. Arylimidamide benzimidazole derivatives (23a–23c, 24a–24c, 25a–25c) were prepared from the corresponding 5(6)-aminobenzimidazole precursors (20a–20c, 21a–21c, 22a–22c) and prepared S-(2-naphtylmethyl)thiobenzimidate hydrobromide 4. 5(6)-Aminobenzimidazole precursors were obtained by a reduction reaction from 5(6)-nitrobenzimidazoles (17a–17c, 18a–18c, 19a–19c) prepared by condensation of bisulfite aducts of the corresponding benzaldehyde precursors (13a–13c, 14a–14c, 15a–15c) with 4-nitro-o-phenylenediamine 16. Benzyl- (13a–13c), picolyl- (14a–14c) and ethynylmorpholine- (15a–15c) 1,2,3-triazole derivatives of benzaldehyde were prepared by regioselective Cu(I)-catalyzed cycloaddition from the prepared 4-(prop-2-ynyloxy)benzaldehydes (6a–6c) and the corresponding azides. The structures of all newly synthesized compounds were confirmed by the means of 1H NMR and 13C NMR spectroscopy. |
