Scandium triflate-catalyzed nucleophilic additions to indolylmethyl Meldrum's acid derivatives via a gramine-type fragmentation: Synthesis of substituted indolemethanes

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10534-10540

  Armstrong, Erin L ^a   Grover, Huck K ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; MELDRUM'S ACIDS; MOLECULAR COMPLEXITY; NUCLEOPHILIC ADDITIONS; NUCLEOPHILIC DISPLACEMENT; SCANDIUM TRIFLATE;

CHEMICAL COMPOUNDS;

SCANDIUM;

ELECTROPHILE; GRAMINE; INDOLE DERIVATIVE; INDOLEMETHANE DERIVATIVE; INDOLYLMETHYL MELDRUM ACID DERIVATIVE; NUCLEOPHILE; SCANDIUM; SCANDIUM TRIFLATE; SOLVENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; FRAGMENTATION REACTION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; REACTION TIME; SOLVENT EFFECT; STOICHIOMETRY; TEMPERATURE;

CATALYSIS; DIOXANES; HETEROCYCLIC COMPOUNDS; INDOLES; MESYLATES; MOLECULAR STRUCTURE; SCANDIUM;

EID: 84886423681     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4017524     Document Type: Article

References (49)

1. Kam, T. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Eds.; Pergamon Press: Amsterdam, 1999; Vol. 4.
2. Veluri, B.; Oka, I.; Wagner-Dobler, I.; Laatsch, H. J. Nat. Prod. 2003, 66, 1520
3. Bell, R.; Carmeli, S. J. Nat. Prod. 1994, 57, 1587
4. Zhu, Y.-p.; Liu, M.-c.; Jia, F.-c.; Yuan, J.-j.; Gao, Q.-h.; Lian, M.; Wu, A.-x. Org. Lett. 2012, 14, 3392
5. Xia, D.; Wang, Y.; Du, Z.; Zheng, Q.-Y.; Wang, C. Org. Lett. 2012, 14, 588
6. Das, P. J.; Das, J. Tetrahedron Lett. 2012, 53, 4718
7. Mendes, S. R.; Thurow, S.; Fortes, M.; Penteado, F.; Lenardão, E. J.; Alves, D.; Perin, G.; Jacob, R. G. Tetrahedron Lett. 2012, 53, 5402
8. Pathak, T. P.; Osiak, J. G.; Vaden, R. M.; Welm, B. E.; Sigman, M. S. Tetrahedron 2012, 68, 5203
9. Yang, H.; Cui, B.; Wu, G.; Miao, Z.; Chen, R. Tetrahedron Lett. 2012, 68, 4830
10. Kamble, S.; Rashinkar, G.; Kumbhar, A.; Salunkhe, R. Synth. Commun. 2012, 42, 756
11. Rani, V. J.; Vani, K. V.; Rao, C. V. Synth. Commun. 2012, 42, 2048
12. Reddy, B. V. S.; Rajeswari, N.; Sarangapani, M.; Prashanthi, Y.; Ganji, R. J.; Addlagatta, A. Bioorg. Med. Chem. Lett. 2012, 22, 2460
13. Yang, Q.; Wang, L.; Guo, T.; Yu, Z. J. Org. Chem. 2012, 77, 8355
14. Bianchi, L.; Giorgi, G.; Maccagno, M.; Petrillo, G.; Scapolla, C.; Tavani, C. Tetrahedron Lett. 2012, 53, 752
15. Sapeta, K.; Lebold, T. P.; Kerr, M. A. Synlett 2011, 1495
16. England, D. B.; Kerr, M. A. J. Org. Chem. 2005, 70, 6519
17. Banfield, S. C.; England, D. B.; Kerr, M. A. Org. Lett. 2001, 3, 3325
18. Emmett, M. R.; Kerr, M. A. Org. Lett. 2011, 13, 4180
19. Grover, H. K.; Lebold, T. P.; Kerr, M. A. Org. Lett. 2011, 13, 220
20. Johansen, M. B.; Kerr, M. A. Org. Lett. 2010, 12, 4956
21. Magolan, J.; Kerr, M. A. Org. Lett. 2006, 8, 4561
22. Gibe, R.; Kerr, M. A. J. Org. Chem. 2002, 67, 6247
23. England, D. B.; Kerr, M. A. Can. J. Chem. 2002, 80, 992
24. Karadoelian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2010, 49, 1133
25. Lebold, T. P.; Kerr, M. A. Org. Lett. 2008, 10, 997
26. Lebold, T. P.; Kerr, M. A. Org. Lett. 2007, 9, 1883
27. Mahoney, S. J.; Lou, T.; Bondarenko, G.; Fillion, E. Org. Lett. 2012, 14, 3474
28. Lou, T.; Liao, E.-T.; Wilsily, A.; Fillion, E. Org. Synth. 2012, 89, 115
29. Dumas, A. M.; Fillion, E. Acc. Chem. Res. 2010, 43, 440
30. Mahoney, S. J.; Dumas, A. M.; Fillion, E. Org. Lett. 2009, 11, 5346
31. Wilsily, A.; Fillion, E. J. Org. Chem. 2009, 74, 8583
32. Fillion, E.; Zorzitto, A. K. J. Am. Chem. Soc. 2009, 131, 14608
33. Mahoney, S. J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50, 4706
34. Fillion, E.; Fishlock, D. Tetrahedron 2009, 65, 6682
35. Dumas, A. M.; Fillion, E. Org. Lett. 2009, 11, 1919
36. Fillion, E.; Wilsily, A.; Fishlock, D. J. Org. Chem. 2009, 74, 1259
37. Wilsily, A.; Fillion, E. Org. Lett. 2008, 10, 2801
38. Fillion, E.; Dumas, A. M. J. Org. Chem. 2008, 73, 2920
39. Janikowska, K.; Makowiec, S.; Rachoń, J. Helv. Chim. Acta 2013, 96, 978
40. Allen, J. C.; Kociok-Kohn, G.; Frost, C. G. Org. Biomol. Chem. 2012, 10, 32
41. Li, H.; Wen, Z.; Jin, L.; Kan, Y.; Yin, B. Chem. Commun. 2012, 48, 11659
42. Chandan, N.; Thompson, A. L.; Moloney, M. G. Org. Biomol. Chem. 2012, 10, 7863
43. Trost, B. M.; Morris, P. J.; Sprague, S. J. J. Am. Chem. Soc. 2012, 134, 17823
44. Kimmel, K. L.; Weaver, J. D.; Lee, M.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 9058
45. Krabbe, S. W.; Do, T. D.; Johnson, J. S. Org. Lett. 2012, 14, 5932
46. Sautler, B.; Lyons, S. E.; Webb, M. R.; Procter, D. J. Org. Lett. 2012, 14, 146
47. This work is complementary to the work of Deb and Bhuyan, who reported a similar reaction using barbituric acid derivatives. See: Deb, L.; Bhuyan, P. J. Synthesis 2008, 2891
48. Oikawa, Y.; Hirasawa, H.; Yonemitsu, O. Tetrahedron Lett. 1978, 19, 1759
49. We have observed the deactivation of such catalysts by DMF previously. See: England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704