Synthesis, Inhaltsverzeichnis Synthesis 2016; 48(21): 3713-3718DOI: 10.1055/s-0035-1562436 paper © Georg Thieme Verlag Stuttgart · New YorkFacile Synthesis of N-Substituted Benzimidazoles Santosh Kurhade University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands eMail: a.s.s.domling@rug.nl , Arianna Rossetti University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands eMail: a.s.s.domling@rug.nl , Alexander Dömling University of Groningen, Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands eMail: a.s.s.domling@rug.nl› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A particularly mild and efficient one-pot synthesis of N-substituted benzimidazole derivatives was developed. 2-Fluoro-5-nitrophenylisocyanide reacts with a diverse set of primary amines to afford the respective products in moderate to very good yield (35–95%; 20 examples). Key words Key wordsisocyanides - nucleophilic aromatic substitution - benzimidazole Volltext Referenzen References For reviews, see: 1a Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Rao MV. Mini-Rev. Med. Chem. 2006; 6: 71 1b Wexler RR, Greenlee WJ, Irvin JD, Goldberg MR, Prendergast K, Smith RP, Timmermans PB. M. W. M. J. Med. Chem. 1996; 39: 625 1c Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893 2 Spasov AA, Yozhitsa IN, Bugaeva LI, Anisimova VA. J. Pharm. Chem. 1999; 33: 232 For reviews, see: 3a Bansal Y, Silakari O. Bioorg. Med. Chem. 2012; 20: 6208 3b Shah K, Chhabra S, Shrivastava PM. Med. Chem. Res. 2013; 22: 5077 3c Narasimhan B, Sharma D, Kumar P. Med. Chem. Res. 2012; 21: 269 3d Khokra SL, Choudhary D. Asian J. Bio. Pharm. Sci. 2011; 3: 476 4a Preston PN. Benzimidazoles and Congeneric Tricyclic Compounds . In The Chemistry of Heterocyclic Compounds . Vol. 40. Weissberger A, Taylor EC. Wiley-VCH; New York: 1981: 6-60 4b Grimmett MR. Imidazoles and their Benzo Derivatives . In Comprehensive Heterocyclic Chemistry . Vol. 5. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 457-487 4c Fujiwara S, Asanuma Y, Shin-ike T, Kambe N. J. Org. Chem. 2007; 72: 8087 4d Lygin AV, de Meijere A. Org. Lett. 2009; 11: 389 4e Lygin AV, de Meijere A. J. Org. Chem. 2009; 74: 4554 5a Jaisinghani HG, Khadikar BM. Synth. Commun. 1999; 29: 3693 5b Hayat S, Atta-ur-Rahman Choudhari MI, Khan KM, Schumann W, Bayer E. Tetrahedron 2001; 57: 9951 5c Rivas FM, Giessert AJ, Diver ST. J. Org. Chem. 2002; 67: 1708 5d Wen-Chung S, Mario L, Oljan R. Tetrahedron Lett. 2003; 44: 6943 5e Kore R, Srivastava R. J. Mol. Catal. A: Chem. 2011; 44: 3371 5f O’Connell JM, Moriaty E, Aldabbagh F. Synthesis 2012; 44: 3371 5g Pereira KC, Poter AL, DeBoef B. Tetrahedron Lett. 2014; 55: 1729 5h Chelucci G, Figus S. J. Mol. Catal. A: Chem. 2014; 393: 191 5i Aksenov AV, Smirnov AN, Aksenov NA, Bijieva AS, Aksenova IV, Rubin M. Org. Biomol. Chem. 2015; 13: 4289 For isocyanide-based synthesis, see: 5j Nenajdenko VG. Isocyanide Chemistry: Applications in Synthesis and Material Science. Wiley-VCH; Weinheim: 2012 5k Tempest P, Ma V, Thomas S, Hua Z, Kelly MG, Hulme C. Tetrahedron Lett. 2001; 42: 4959 5l Xu Z, Ayaz M, Cappelli AA, Hulme C. ACS Comb. Sci. 2012; 14: 460 6 Lygin AV, de Meijere A. Eur. J. Org. Chem. 2009; 5138 7 Boratyński PJ, Nowak AE, Skarżewski J. Synthesis 2015; 47: 3797 8 Dömling A, Antuch W, Beck B, Schauer-Vukašinović V. Bioorg. Med. Chem. Lett. 2008; 18: 4115 Zusatzmaterial Zusatzmaterial Supporting Information
