Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12144-12153

  Kuznetsov, Alexey ^a   Makarov, Anton ^b   Rubtsov, Aleksandr E ^b   Butin, Alexander V ^b   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b PERM STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

C-2 POSITIONS; IN-SITU FORMATIONS; ONE-POT SYNTHESIS; UNSATURATED KETONES;

CARBON DIOXIDE; FUNCTIONAL GROUPS; KETONES; ORGANIC POLLUTANTS; SCAFFOLDS;

AROMATIC COMPOUNDS;

ALCOHOL DERIVATIVE; BRONSTED ACID; FUNCTIONAL GROUP; FURAN DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; REACTION OPTIMIZATION;

ACIDS; BENZYL ALCOHOLS; FURANS; INDOLES; MOLECULAR STRUCTURE;

EID: 84890193863     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402132p     Document Type: Article

References (47)

1. For a review, see: Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777
2. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553
3. Hashmi, A. S. K.; Weyrauch, J. P.; Rudolph, M.; Kurpejovic, E. Angew. Chem., Int. Ed. 2004, 43, 6545
4. Liu, L.; Gao, Y.; Che, C.; Wu, N.; Wang, D. Z.; Li, C.-C.; Yang, Z. Chem. Commun. 2009, 662
5. Chen, Y.; Lu, Y.; Li, G.; Liu, Y. Org. Lett. 2009, 11, 3838
6. Chen, Y.; Li, G.; Liu, Y. Adv. Synth. Catal. 2011, 353, 392
7. Chen, Y.; Liu, Y. J. Org. Chem. 2011, 76, 5274
8. Petronijevic, F. R.; Wipf, P. J. Am. Chem. Soc. 2011, 133, 7704
9. Zubkov, F. I.; Airiyan, I. K.; Ershova, J. D.; Galeev, T. R.; Zaytsev, V. P.; Nikitina, E. V.; Varlamov, A. V. RSC Adv. 2012, 2, 4103
10. Huguet, N.; Lebœuf, D.; Echavarren, A. M. Chem.-Eur. J. 2013, 19, 6581
11. Harris, J. M.; Padwa, A. J. Org. Chem. 2003, 68, 4371
12. Kelly, A. R.; Kerrigan, M. H.; Walsh, P. J. J. Am. Chem. Soc. 2008, 130, 4097
13. Bi, J.; Aggarwal, V. K. Chem. Commun. 2008, 120
14. Zhou, X.; Wu, W.; Liu, X.; Lee, C.-S. Org. Lett. 2008, 10, 5525
15. Fructos, M. R.; Alvarez, E.; Mar Diaz-Requejo, M.; Perez, P. J. J. Am. Chem. Soc. 2010, 132, 4600
16. El Kaïm, L.; Grimaud, L.; Wagschal, S. Chem. Commun. 2011, 1887
17. Yin, B.; Cai, C.; Zeng, G.; Zhang, R.; Li, X.; Jiang, H. Org. Lett. 2012, 14, 1098
18. Uchuskin, M. G.; Pilipenko, A. S.; Serdyuk, O. V.; Trushkov, I. V.; Butin, A. V. Org. Biomol. Chem. 2012, 10, 7262
19. Trushkov, I. V.; Nevolina, T. A.; Shcherbinin, V. A.; Sorotskaya, L. N.; Butin, A. V. Tetrahedron Lett. 2013, 54, 3974
20. Parr, B. T.; Green, S. A.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716
21. Zhang, S.-Y.; Tu, Y.-Q.; Cao, X.-P. Chem.-Eur. J. 2013, 19, 5246
22. Sundberg, R. J., Ed. Indoles; Academic Press: London, 1996.
23. Joule, J. A. Indole and its Derivatives. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme Verlag:: Stuttgart, 2000; Vol. 10, Chapter 10.13.
24. Maes, B. U. W. Heterocyclic Scaffolds II. Reactions and Applications of Indoles. In Topics in Heterocycic Chemistry; Gribble, G. W., Ed.; Springer-Verlag: Berlin, 2010; Vol. 26.
25. Shiri, M. Chem. Rev. 2012, 112, 3508
26. Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250
27. Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538
28. van Putten, R.-J.; van der Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G. Chem. Rev. 2013, 113, 1499
29. Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084
30. Butin, A. V.; Smirnov, S. K.; Stroganova, T. A.; Bender, W.; Krapivin, G. D. Tetrahedron 2007, 63, 474
31. Rhee, J. U.; Krische, M. J. Org. Lett. 2005, 7, 2493
32. Li, Z.; Zhang, J.; Brouwer, C.; Yang, C.-G.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175
33. Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179
34. Hashmi, A. S. K. Catal. Today 2007, 122, 211
35. Crich, D.; Vinogradova, O. J. Org. Chem. 2006, 71, 8473
36. Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440
37. Sun, K.; Liu, S.; Bec, P. M.; Driver, T. G. Angew. Chem., Int. Ed. 2011, 50, 1702
38. Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562
39. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452
40. Fleming, I.; Frackenpohl, J.; Ila, H. J. Chem. Soc., Perkin Trans. 1 1998, 1229
41. Schrader, T. O.; Johnson, B. R.; Lopez, L.; Kasem, M.; Gharbaoui, T.; Sengupta, D.; Buzard, D.; Basmadjian, C.; Jones, R. M. Org. Lett. 2012, 14, 6306
42. For the importance of dihydropyrroloindoles, see: Ding, Z.; Yoshikai, N. Angew. Chem., Int. Ed. 2013, 52, 8574 and references cited therein
43. Haner, J.; Jack, K.; Nagireddy, J. R.; Raheem, M.-A.; Durham, R.; Tam, W. Synthesis 2011, 731
44. Hechavarría Fonseca, M.; Eibler, E.; Zabel, M.; König, B. Tetrahedron: Asymmetry 2003, 14, 1989
45. Fan, C.; Vederas, J. C. Org. Biomol. Chem. 2012, 10, 5815
46. Poloukhtine, A.; Rassadin, V.; Kuzmin, A.; Popik, V. V. J. Org. Chem. 2010, 75, 5953
47. Gao, W.-C.; Jiang, S.; Wang, R.-L.; Zhang, C. Chem. Commun. 2013, 4890