Facile and efficient synthesis of a new class of bis(3′-indolyl)pyridine derivatives via one-pot multicomponent reactions

Tetrahedron Letters

Volumn 49, Issue 11, 2008, Pages 1777-1781

  Zhu, Song Lei ^a,b   Ji, Shun Jun ^a   Su, Xiao Ming ^a   Sun, Chang ^a   Liu, Yu ^a  

^a SOOCHOW UNIVERSITY   (China)

^b XUZHOU MEDICAL UNIVERSITY   (China)

Author keywords

3,5 Dicyanopyridine; Bisindole; Microwave irradiation; Multicomponent reactions

Indexed keywords

2,4 BIS(3 INDOLYL)PYRIMIDINE DERIVATIVE; 2,5 BIS(3 INDOLYL)THIOPHENE DERIVATIVE; 3 CYANOACETYL INDOLE DERIVATIVE; 3,5 DICYANO 2,6 DI(3' INDOLYL)PYRIDINE DERIVATIVE; ALDEHYDE; AMMONIUM ACETATE; BIS(3' INDOLYL)PYRIDINE DERIVATIVE; HAMACANTHIN B; INDOLE DERIVATIVE; NORTOPSENTIN A; NORTOPSENTIN B; NORTOPSENTIN C; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; MELTING POINT; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS;

EID: 38949115627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.054     Document Type: Article

References (34)

1. Houlihan W.J., Remers W.A., and Brown R.K. Indoles: Part I (1992), Wiley, New York, NY
2. Sundberg R.J. The Chemistry of Indoles (1996), Academic Press, New York
3. Casapullo A., Bifulco G., Bruno I., and Riccio R. J. Nat. Prod. 63 (2000) 447
4. Bao B., Sun Q., Yao X., Hong J., Lee C.O., Sim C.J., Im K.S., and Jung J.H. J. Nat. Prod. 68 (2005) 711
5. Skibo E.B., Xing C., and Dorr R.T. J. Med. Chem. 44 (2001) 3545
6. Gupta L., Talwar A., Palne N.S., Gupta S., and Chauhan P.M.S. Bioorg. Med. Chem. Lett. 17 (2007) 4075
7. Kaniwa K., Arai M.A., Li X., and Ishibashi M. Bioorg. Med. Chem. Lett. 17 (2007) 4254
8. Sakemi S., and Sun H.H. J. Org. Chem. 56 (1991) 4304
9. Kawasaki I., Yamashita M., and Ohta S. Chem. Pharm. Bull. 44 (1996) 1831
10. Kouko T., Matsumura K., and Kawasaki T. Tetrahedron 61 (2005) 2309
11. Higuchi K., Takei R., Kouko T., and Kawasaki T. Synthesis (2007) 669
12. Jiang B., Xiong X., and Yang C. Bioorg. Med. Chem. Lett. 11 (2001) 475
13. Jiang B., and Gu X. Bioorg. Med. Chem. Lett. 10 (2000) 363
14. Gu X., Wan X., and Jiang B. Bioorg. Med. Chem. Lett. 9 (1999) 569
15. Jiang B., Xiong X., and Yang C. Bioorg. Med. Chem. 9 (2001) 1149
16. Xiong W., Yang C., and Jiang B. Bioorg. Med. Chem. 9 (2001) 1773
17. Diana P., Carbone A., Barraja P., Montalbano L., Martorana A., Dattolo G., Gia O., Via D.L., and Cirrincione G. Bioorg. Med. Chem. Lett. 17 (2007) 2342
18. Tietze L.F. Chem. Rev. 96 (1996) 115
19. Dömling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3169
20. Weber L. Drug Discovery Today 7 (2002) 143
21. Dömling A. Curr. Opin. Chem. Biol. 6 (2002) 306
22. Ji S.-J., Wang S.-Y., Zhang Y., and Loh T.-P. Tetrahedron 60 (2004) 2051
23. Gu D.-G., Ji S.-J., Jiang Z.-Q., Zhou M.-F., and Loh T.-P. Synlett (2005) 959
24. Wang S.-Y., and Ji S.-J. Tetrahedron 62 (2006) 1527
25. Zeng X.-F., and Ji S.-J. Lett. Org. Chem. 3 (2006) 374
26. Wang S.-Y., and Ji S.-J. Synlett (2007) 2222
27. Zhu S.-L., Ji S.-J., and Zhang Y. Tetrahedron 63 (2007) 9365
28. Labaudiniere R., Dereu N., Cavy F., Guillet M.C., Marquis O., and Terlain B. J. Med. Chem. 35 (1992) 4315
29. Kreher R., and Wagner P.H. Chem. Ber. 113 (1980) 3675
30. Slatt J., Romero I., and Bergman J. Synthesis (2004) 2760
31. Devi I., Kumarb B.S.D., and Bhuyan P.J. Tetrahedron Lett. 44 (2003) 8307
32. Evdokimov N.M., Magedov I.V., Kireev A.S., and Kornienko A. Org. Lett. 8 (2006) 899
33. 5O: M, 467.1746].
34. Crystallographic data for the structures of 3f and 4 reported in this paper have been deposited at the Cambridge Crystallographic Data Centre with No. CCDC 632750 and 632751, respectively.