Facile one-pot assembly of imidazotriazolobenzodiazepines via indium(III)-catalyzed multicomponent reactions

Organic Letters

Volumn 15, Issue 17, 2013, Pages 4492-4495

  Nguyen, Huy H ^a   Palazzo, Teresa A ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; AZIDE; FUSED HETEROCYCLIC RINGS; INDIUM; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AMINES; AZIDES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDIUM; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 84883791216     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402045h     Document Type: Article

References (40)

1. Laufer, S. A.; Zimmermann, W.; Ruff, K. J. J. Med. Chem. 2004, 47, 6311-25
2. Jadhav, V. B.; Kulkarni, M. V.; Rasal, V. P.; Biradar, S. S.; Vinay, M. D. Eur. J. Med. Chem. 2008, 43, 1721-29
3. Alkahtani, H. M.; Abbas, A. Y.; Wang, S. Bioorg. Med. Chem. Lett. 2012, 22, 1317-21
4. Seto, M.; Aikawa, K.; Miyamoto, N.; Aramaki, Y.; Kanzaki, N.; Takashima, K.; Kuze, Y.; Iizawa, Y.; Baba, M.; Shiraishi, M. J. Med. Chem. 2006, 49, 2037-48
5. Gupta, P.; Hameed, S.; Jain, R. Eur. J. Med. Chem. 2004, 39, 805-14
6. Raj, R.; Singh, P.; Haberkern, N. T.; Faucher, R. M.; Patel, N.; Land, K. M.; Kumar, V. Eur. J. Med. Chem. 2013, 63, 897-906
7. Cheng, H.; Wan, J.; Lin, M. I.; Liu, Y.; Lu, X.; Liu, J.; Xu, Y.; Chen, J.; Tu, Z.; Cheng, Y. E. J. Med. Chem. 2012, 55, 2144-53
8. Regueiro-Ren, A.; Xue, Q. M.; Swidorski, J. J.; Gong, Y. F.; Mathew, M.; Parker, D. D.; Yang, Z.; Eggers, B.; D'Arienzo, C.; Sun, Y. J. Med. Chem. 2013, 56, 1656-69
9. Keller, O.; Steiger, N.; Sternbach, L. H. U.S. Patent 3,442,946, 1969.
10. Tashma, Z.; Raveh, L.; Liani, H.; Alkalay, D.; Givoni, S.; Kapon, J.; Cohen, G.; Alcalay, M.; Grauer, E. J. Appl. Toxicol. 2001, 21, S115
11. Walser, A. U.S. Patent 4,226,771, 1980.
12. Mohapatra, D. K.; Maity, P. K.; Shabab, M.; Khan, M. I. Bioorg. Med. Chem. Lett. 2009, 19, 5241-45
13. Donald, J. R.; Martin, S. F. Org. Lett. 2011, 13, 852-55
14. Donald, J. R.; Wood, R. R.; Martin, S. F. ACS Comb. Sci. 2012, 14, 135-43
15. Hooyberghs, G.; De Coster, H.; Vachhani, D. D.; Ermolat'ev, D. S.; Van der Eycken, E. V. Tetrahedron 2013, 69, 4331-37
16. Kumar, A.; Li, Z.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Org. Lett. 2013, 15, 1874-77
17. Vachhani, D. D.; Kumar, A.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Eur. J. Org. Chem. 2013, 1223-27
18. Gracias, V.; Darczak, D.; Gasiecki, A. F.; Djuric, S. W. Tetrahedron Lett. 2005, 46, 9053-56
19. Bredereck, H.; Theilig, G. Chem. Ber. 1953, 86, 88-96
20. Japp, F. R.; Robinson, H. H. Ber. Dtsch. Chem. Ges. 1882, 15, 1268-70
21. Radziszewsky, B. Ber. Dtsch. Chem. Ges. 1882, 15, 1493-96
22. Debus, H. Justus Liebigs Ann. Chem. 1858, 107, 199-208
23. Kunckell, F. Ber. Dtsch. Chem. Ges. 1901, 34, 637-42
24. van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153-59
25. Sharma, S. D.; Hazarika, P.; Konwar, D. Tetrahedron Lett. 2008, 49, 2216-20
26. Sangshetti, J. N.; Kokare, N. D.; Kothrkara, S. A.; Shinde, D. B. J. Chem. Sci. 2008, 120, 463-7
27. Samai, S.; Nandi, G. C.; Singh, P.; Singh, M. S. Tetrahedron 2009, 65, 10155-61
28. Sadeghi, B.; Mirjalili, B. B. F.; Hashemi, M. M. Tetrahedron Lett. 2008, 49, 2575-77
29. Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R. K.; Ethayathulla, A. S.; Dey, S.; Singh, T. P. J. Mol. Catal. A: Chem. 2007, 265, 177-182
30. Heravi, M. M.; Derikvand, F.; Haghighi, M. Monatsh. Chem. 2008, 139, 31-33
31. Majumdar, K. C.; Ray, K. Synthesis 2011, 23, 3767-83
32. Arigela, R. K.; Mandadapu, A. K.; Sharma, S. K.; Kumar, B.; Kundu, B. Org. Lett. 2012, 14, 1804-07
33. Mohapatra, D. K.; Maity, P. K.; Shabab, M.; Khan, M. I. Bioorg. Med. Chem. Lett. 2009, 19, 5241-45
34. Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439-41
35. Oliva, A. I.; Christmann, U.; Font, D.; Cuevas, F.; Ballester, P.; Buschmann, H.; Torrens, A.; Yenes, S.; Pericas, M. A. Org. Lett. 2008, 10, 1617-19
36. Conrad, W. E.; Rodriguez, K. X.; Nguyen, H. H.; Fettinger, J. C.; Haddadin, M. J.; Kurth, M. J. Org. Lett. 2012, 14, 3870-73
37. Guggenheim, K. G.; Toru, H.; Kurth, M. J. Org. Lett. 2012, 14, 3732-35
38. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702-5
39. Roy, S.; Anoop, A.; Biradha, K.; Basak, A. Angew. Chem., Int. Ed. 2011, 50, 8316-19
40. Kudo, M.; Perseghini, G.; Fu, C. Angew. Chem., Int. Ed. 2006, 45, 1282-84