Synthesis of benzimidazole-fused heterocycles by intramolecular oxidative C-N bond formation using hypervalent iodine reagents

Synthesis

Volumn , Issue 20, 2011, Pages 3235-3240

  Kutsumura, Noriki ^a   Kunimatsu, Shinichi ^a   Kagawa, Kimiko ^a   Otani, Takashi ^a   Saito, Takao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

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

Indexed keywords

BOND FORMATION; BOND FORMING; C-N COUPLING; HETEROCYCLES; HYPERVALENT IODINE REAGENTS; MILD CONDITIONS;

IODINE;

ANILINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZIMIDAZOLE FUSED HETEROCYCLIC DERIVATIVE; HETEROCYCLIC COMPOUND; IODINE; N (1 AZAHETEROCYCLE 2 YL)ANILINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; OXIDATION; SYNTHESIS;

EID: 80053910860     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260192     Document Type: Article

References (29)

1. Breslow R, Gellman S H., J. Am. Chem. Soc. 1983 105 6728
2. Espino C G., DuBois J, Angew. Chem. Int. Ed. 2001 40 598
3. Espino C G., Wehn P M., Chow J, DuBois J, J. Am. Chem. Soc. 2001 123 6935
4. Misu Y, Togo H, Org. Biomol. Chem. 2003 1 1342
5. Amano Y, Nishiyama S, Tetrahedron Lett. 2006 47 6505
6. Zhu J, Xie H, Chen Z, Li S, Wu Y, Synlett 2009 3299
7. Pardo L M., Tellitu I, Domínguez E, Synthesis 2010 971
8. Al-Rashood K A., Abdel-Aziz H A., Molecules 2010 15 3775
9. Hranjec M, Piantanida I, Kralj M, uman L, Paveli K, Karminski-Zamola G, J. Med. Chem. 2008 51 4899
10. Song X, Vig B S., Lorenzi P L., Drach J C., Townsend L B., Amidon G L., J. Med. Chem. 2005 48 1274
11. Paramashivappa R, PhaniKumar P, SubbaRao P V., SrinivasaRao A, Bioorg. Med. Chem. Lett. 2003 13 657
12. Kohara Y, Kubo K, Imamiya E, Wada T, Inada Y, Naka T, J. Med. Chem. 1996 39 5228
13. Kubo K, Kohara Y, Yoshimura Y, Inada Y, Shibouta Y, Furukawa Y, Kato T, Nishikawa K, Naka T, J. Med. Chem. 1993 36 2343
14. Gupta R P., Larroquette C A., Agrawal K C., J. Med. Chem. 1982 25 1342
15. Evans D A., Faul M M., Bilodeau M T., J. Am. Chem. Soc. 1994 116 2742
16. Evans D A., Faul M M., Bilodeau M T., J. Org. Chem. 1991 56 6744
17. Miyamoto M, Takashima Y, Kimura Y, Macromolecules 1998 31 6822
18. Jen T, Van Hoeven H, Groves W, McLean R A., Loev B, J. Med. Chem. 1975 18 90
19. Heinelt U, Schultheis D, Jäger S, Lindenmaier M, Pollex A, Beckmann H S., Tetrahedron 2004 60 9883
20. For 1a, 1b, 1c, 1f, and 1g, see:, Tiler M, Tetrahedron Lett. 1959 12
21. For 1e and 5a, see:, Caroon J M., Fisher L E., Heterocycles 1991 32 459
22. For 3a and 3b, see:, Avalos M, Babiano R, Cintas P, Jiménez J L., Palacios J C., Valencia C, Heterocycles 1993 35 1237
23. For 5c, see:, Yella R, Patel B K., J. Comb. Chem. 2010 12 754
24. Smoliski S, Czarny A, Bull. Chem. Soc. Jpn. 1979 52 930
25. Ogura H, Itoh T, Shimada Y, Chem. Pharm. Bull. 1968 16 2167
26. Caroon J M., Fisher L E., Heterocycles 1991 32 459
27. Iwaki T, Yasuhara A, Sakamoto T, J. Chem. Soc., Perkin Trans. 1 1999 1505
28. Wang H, Wang Y, Peng C, Zhang J, Zhu Q, J. Am. Chem. Soc. 2010 132 13217
29. Loones K T. J., Maes B U. W., Meyers C, Deruytter J, J. Org. Chem. 2006 71 260