Synthesis of substituted indole from 2-aminobenzaldehyde through [1,2]-aryl shift

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 7033-7036

  Levesque, Patrick ^a   Fournier, Pierre André ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRANILIC ACID; BUILDING BLOCKES; ETHYL DIAZOACETATE; REGIOCHEMICAL CONTROL; SIMPLE METHOD; SUBSTITUTED INDOLES;

ACIDS;

FUNCTIONAL GROUPS;

3 ETHOXYCARBONYLINDOLE DERIVATIVE; AMINOBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; ETHYL 1 BENZYLINDOLE 3 CARBOXYLIC ACID; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; SYNTHESIS;

ALDEHYDES; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77957919304     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1016713     Document Type: Article

References (47)

1. Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278-311
2. Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73-103
3. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930
4. Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2007, 24, 843-868
5. Rahman, A.; Basha, A. Indole Alkaloids; Harwood Academic Publishers: Amsterdam, The Netherlands, 1998; p 141.
6. Gupta, R. R. Heterocyclic Chemistry; Springer Publishing: New York, 1999; Vol. 2, p 193.
7. For a general review on indole synthesis, see: Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911
8. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075
9. For some recent methods, see: Du, Y.; Liu, R.; Linn, G.; Zhao, K. Org. Lett. 2006, 8, 5919-5922
10. Du, Y.; Chang, J.; Reiner, J.; Zhao, K. J. Org. Chem. 2008, 73, 2007-2010
11. Schlosser, M.; Ginanneschi, A.; Leroux, F. Eur. J. Org. Chem. 2006, 2956-2969
12. Kraus, G. A.; Guo, H. Org. Lett. 2008, 10, 3061-3063
13. Robinson, B. The Fisher Indole Synthesis; John Wiley and Sons: Chichester, UK, 1982.
14. For a review on metal-catalyzed synthesis of indoles, see: Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2210
15. Cacchi, A.; Fabrizi, G. Chem. Rev. 2005, 105, 2873-2920
16. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160 For recent variants of the Larock indole synthesis
17. see: Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474-16475
18. Leogane, O.; Lebel, H. Angew. Chem., Int. Ed. 2008, 47, 350-352
19. Wurtz, S.; Neumann, J. J.; Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230-7233
20. Jia, Y.; Zhu, J. J. Org. Chem. 2006, 71, 7826-7834
21. Nakamura, Y.; Ukita, T. Org. Lett. 2002, 4, 2317-2320
22. Pei, T.; Chen, C.-Y.; Dormer, P. G.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4231-4233
23. Pei, T.; Tellers, D. M.; Streckfuss, E. C.; Chen, C.-Y.; Davies, I. W. Tetrahedron 2009, 65, 3285-3291
24. Islam, M. S.; Brennan, C.; Wang, Q.; Hossain, M. M. J. Org. Chem. 2006, 71, 4675-4C677
25. Dudley, M. E.; Morshed, Md. M.; Brennan, C. L.; Islam, M. S.; Ahmad, M. S.; Atuu, M.-R.; Branstetter, B.; Hossain, M. M. J. Org. Chem. 2004, 69, 7599-7608
26. For leading references on acid-catalyzed reactions of substituted diazomethanes and carbonyls, see: Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434-2435
27. Hashimoto, T.; Miyamoto, H.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 11280-11281
28. Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 6614-6617
29. Moebius, D. C.; Kingsbury, J. S. J. Am. Chem. Soc. 2009, 131, 878-879
30. Wommack, A. J.; Moebius, D. C.; Travis, A. L.; Kingsbury, J. S. Org. Lett. 2009, 11, 3202-3205
31. Li, W.; Wang, J.; Hu, X.; Shen, K.; Wang, W.; Chu, Y.; Lin, L.; Liu, X.; Feng, X. J. Am. Chem. Soc. 2010, 132, 8532-8533
32. Opie, J. W.; Smith, L. I. Organic Synthesis; Wiley: New York, 1955; Vol. III, pp 56 - 58.
33. Li, J.-F.; Zhao, Y.; Cai, M.-M.; Li, X.-F.; Li, J.-X. Eur. J. Med. Chem. 2009, 44, 2796-2806
34. Haddach, A. A.; Kelleman, A.; Deaton-Rewolinski, M. V. Tetrahedron Lett. 2002, 43, 399-402
35. Yu, H.; Yu, Z. Angew. Chem., Int. Ed. 2009, 48, 2929-2933
36. Sanz, R.; Castroviejo, M. P.; Guilarte, V.; Perez, A.; Fananas, F. J. J. Org. Chem. 2007, 72, 5113-5118
37. Murakami, Y.; Watanabe, T.; Kobayashi, A.; Yokoyama, Y. Synthesis 1984, 738-740
38. Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1996, 61, 1916-1917
39. Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609
40. Malapel-Andrieu, B.; Merour, J.-Y. Tetrahedron 1998, 54, 11079-11094
41. Stearman, C. J.; Wilson, M.; Padwa, A. J. Org. Chem. 2009, 74, 3491-3499
42. Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujvary, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984-3999
43. Pedras, M. S. C.; Zheng, Q.-A.; Gadagi, R. A. Chem Commun. 2007, 368-370
44. Performing the reaction at a lower temperature or at various concentrations had no effect on reaction yield.
45. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726
46. Benzaldehydes 1 were readily prepared on gram scale from the corresponding anthranilic acids. See the Supporting Information for details.
47. Further investigations revealed that the desired addition/1,2-aryl shift step occurred quite rapidly (less than 2 h), but the subsequent condensation was very long.