Synthesis of Benzimidazole-Fused Heterocycles by Intramolecular Oxidative C-N Bond Formation Using Hypervalent Iodine Reagents

Abstract

A straightforward approach by dehydrogenative C-N coupling between aryl C-H and N-H bonds using a hypervalent iodine reagent under mild conditions offers a versatile and convenient method for synthesizing various benzimidazole-fused heterocycles.

Key words

hypervalent iodine reagent - C-N bond forming cyclization - benzimidazole-fused heterocycles - straightforward synthesis - mild conditions

References

• 1a Breslow R. Gellman SH. J. Am. Chem. Soc.  1983,  105:  6728 
• 1b Espino CG. Du Bois J. Angew. Chem. Int. Ed.  2001,  40:  598 
• 1c Espino CG. Wehn PM. Chow J. Du Bois J. J. Am. Chem. Soc.  2001,  123:  6935 
• 1d Misu Y. Togo H. Org. Biomol. Chem.  2003,  1:  1342 
• 1e Amano Y. Nishiyama S. Tetrahedron Lett.  2006,  47:  6505 
• 1f Zhu J. Xie H. Chen Z. Li S. Wu Y. Synlett  2009,  3299 
• 1g Pardo LM. Tellitu I. Domínguez E. Synthesis  2010,  971 
• 2a Al-Rashood KA. Abdel-Aziz HA. Molecules  2010,  15:  3775 
• 2b Hranjec M. Piantanida I. Kralj M. Šuman L. Pavelić K. Karminski-Zamola G. J. Med. Chem.  2008,  51:  4899 
• 2c Song X. Vig BS. Lorenzi PL. Drach JC. Townsend LB. Amidon GL. J. Med. Chem.  2005,  48:  1274 
• 2d Paramashivappa R. Phani Kumar P. Subba Rao PV. Srinivasa Rao A. Bioorg. Med. Chem. Lett.  2003,  13:  657 
• 2e Yamasaki N, Imoto T, Murai Y, Hiramura T, Oku T, and Sawada K. inventors; US Patent  6166219.  ; Chem. Abstr. 1997, 127, 135799
• 2f Kohara Y. Kubo K. Imamiya E. Wada T. Inada Y. Naka T. J. Med. Chem.  1996,  39:  5228 
• 2g Kubo K. Kohara Y. Yoshimura Y. Inada Y. Shibouta Y. Furukawa Y. Kato T. Nishikawa K. Naka T. J. Med. Chem.  1993,  36:  2343 
• 2h Gupta RP. Larroquette CA. Agrawal KC. J. Med. Chem.  1982,  25:  1342 
• 3a Evans DA. Faul MM. Bilodeau MT. J. Am. Chem. Soc.  1994,  116:  2742 
• 3b Evans DA. Faul MM. Bilodeau MT. J. Org. Chem.  1991,  56:  6744 
• 4 Miyamoto M. Takashima Y. Kimura Y. Macromolecules  1998,  31:  6822 
• 5a Jen T. Van Hoeven H. Groves W. McLean RA. Loev B. J. Med. Chem.  1975,  18:  90 
• 5b Heinelt U. Schultheis D. Jäger S. Lindenmaier M. Pollex A. Beckmann HS. Tetrahedron  2004,  60:  9883 
• 6a For 1a, 1b, 1c, 1f, and 1g, see: Tišler M. Tetrahedron Lett.  1959,  12 
• 6b For 1e and 5a, see: Caroon JM. Fisher LE. Heterocycles  1991,  32:  459 
• 6c For 3a and 3b, see: Avalos M. Babiano R. Cintas P. Jiménez JL. Palacios JC. Valencia C. Heterocycles  1993,  35:  1237 
• 6d For 5c, see: Yella R. Patel BK. J. Comb. Chem.  2010,  12:  754 
• 6e

  Compounds 1d, 7a, 7b, and 7c were purchased.

• 7 Smoliński S. Czarny A. Bull. Chem. Soc. Jpn.  1979,  52:  930 
• 8 Ogura H. Itoh T. Shimada Y. Chem. Pharm. Bull.  1968,  16:  2167 
• 9 Caroon JM. Fisher LE. Heterocycles  1991,  32:  459 
• 10 Iwaki T. Yasuhara A. Sakamoto T. J. Chem. Soc., Perkin Trans. 1  1999,  1505 
• 11 Wang H. Wang Y. Peng C. Zhang J. Zhu Q. J. Am. Chem. Soc.  2010,  132:  13217 
• 12 Loones KTJ. Maes BUW. Meyers C. Deruytter J. J. Org. Chem.  2006,  71:  260