Synthesis of 2,5-disubstituted 6-azaindoles from substituted aziridines via intramolecular cyclization

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3120-3122

  Lee, Hogyu ^a   Kim, Jun Hee ^a   Lee, Won Koo ^a   Jung, Jae Hoon ^b   Ha, Hyun Joon ^b  

^a Sogang University   (South Korea)

^b Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

6 AZAINDOLE; 6-AZAINDOLE; AZIRIDINE DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; AZIRIDINES; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; PYRROLES;

EID: 84862508355     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301187s     Document Type: Article

References (23)

1. Badarau, E.; Putey, A.; Suzenet, F.; Joseph, B.; Bojarski, A.; Finaru, A.; Guillaumet, G. J. Enzyme Inhib. Med. Chem. 2010, 25, 301-305
2. Popowycz, F.; Mérour, J.-Y.; Joseph, B. Tetrahedron 2007, 63, 8689-8707
3. Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120
4. Jeanty, M.; Blu, J.; Suzenet, F.; Guillaumet, G. R. Org. Lett. 2009, 11, 5142-5145
5. McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3307-3310
6. Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 3651-3653
7. Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162
8. Fang, Y.-Q.; Yuen, J.; Lautens, M. J. Org. Chem. 2007, 72, 5152-5160
9. Song, J. J.; Tan, Z.; Gallou, F.; Xu, J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2005, 70, 6512-6514
10. Plewe, M. B.; Butler, S. L.; R. Dress, K.; Hu, Q.; Johnson, T. W.; Kuehler, J. E.; Kuki, A.; Lam, H.; Liu, W.; Nowlin, D.; Peng, Q.; Rahavendran, S. V.; Tanis, S. P.; Tran, K. T.; Wang, H.; Yang, A.; Zhang, J. J. Med. Chem. 2009, 52, 7211-7219
11. Wang, T.; Yin, Z.; Zhang, Z.; Bender, J. A.; Yang, Z.; Johnson, G.; Yang, Z.; Zadjura, L. M.; D'Arienzo, C. J.; DiGiugno Parker, D.; Gesenberg, C.; Yamanaka, G. A.; Gong, Y.-F.; Ho, H.-T.; Fang, H.; Zhou, N.; McAuliffe, B. V.; Eggers, B. J.; Fan, L.; Nowicka-Sans, B.; Dicker, I. B.; Gao, Q.; Colonno, R. J.; Lin, P.-F.; Meanwell, N. A.; Kadow, J. F. J. Med. Chem. 2009, 52, 7778-7787
12. Twine, S. M.; Murphy, L.; Phillips, R. S.; Callis, P.; Cash, M. T.; Szabo, A. G. J. Phy. Chem. B 2002, 107, 637-645
13. Whelligan, D. K.; Thomson, D. W.; Taylor, D.; Hoelder, S. J. J. Org. Chem. 2010, 75, 11-15
14. Debenham, S. D.; Chan, A.; Liu, K.; Price, K.; Wood, H. B. Tetrahedron Lett. 2005, 46, 2283-2285
15. Kim, J. H.; Lee, S. B.; Lee, W. K.; Yoon, D.-H.; Ha, H.-J. Tetrahedron 2011, 67, 3553-3558
16. Stankovic, S.; D'hooghe, M.; Catak, S.; Eum, H.; Waroquier, M.; Van Speybroeck, V.; De Kimpe, N.; Ha, H.-J. Chem. Soc. Rev. 2012, 41, 643-665
17. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260-11261
18. Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 3651-3653
19. Dekhane, M.; Potier, P.; Dodd, R. H. Tetrahedron 1993, 49, 8139-8146
20. Mahadevan, I.; Rasmussen, M. J. Heterocycl. Chem. 1992, 29, 359-367
21. Niu, Y.-N.; Yan, Z.-Y.; Gao, G.-L.; Wang, H.-L.; Shu, X.-Z.; Ji, K.-G.; Liang, Y.-M. J. Org. Chem. 2009, 74, 2893-2896
22. Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 3651-3653
23. Haddach, A. A.; Kelleman, A.; Deaton-Rewolinski, M. V. Tetrahedron Lett. 2002, 43, 399-402