3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: An "azaenamine" conjugate addition

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5185-5197

  Ghavtadze, Nugzar ^a   Narayan, Rishikesh ^a   Wibbeling, Birgit ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; CARBON ATOMS; CONJUGATE ADDITION; CYCLIZATION REACTIONS; DIASTEREOSELECTIVE; GOOD YIELD; HYDROGEN SHIFTS; KINETIC CONTROL; LOW TEMPERATURES; MICHAEL SYSTEMS; NITROGEN ATOM; QUANTUM CHEMICAL CALCULATIONS; UMPOLUNG;

DICHLOROMETHANE; QUANTUM CHEMISTRY; REDOX REACTIONS; STEREOSELECTIVITY;

CYCLIZATION;

CARBON; CARBONYL DERIVATIVE; DICHLOROMETHANE; ENAMINE; HETEROCYCLIC COMPOUND; HYDROGEN; INDOLE; NITROGEN; TETRALIN DERIVATIVE;

ADDITION REACTION; ARTICLE; ATOM; CALCULATION; CHEMICAL REACTION KINETICS; CIS ISOMER; COMPARATIVE STUDY; CYCLIZATION; DIASTEREOISOMER; LOW TEMPERATURE; MICHAEL ADDITION; OXIDATION REDUCTION REACTION; QUANTUM CHEMISTRY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; TRANS ISOMER;

EID: 79959666016     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200896y     Document Type: Article

References (60)

1. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2008, 3656
2. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2010, 1787
3. Alickmann, D.; Fröhlich, R.; Maulitz, A. H.; Würthwein, E.-U. Eur. J. Org. Chem. 2002, 1523-1537
4. Ghavtadze, N.; Fröhlich, R.; Bergander, K.; Würthwein, E.-U. Synthesis 2008, 3397
5. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2009, 1228
6. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. J. Org. Chem. 2009, 74, 4584
7. Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049
8. Matoba, K.; Itoh, K.; Yamazaki, T.; Nagata, M. Chem. Pharm. Bull. 1981, 29, 2442
9. Matoba, K.; Miyata, Y.; Yamazaki, T. Chem. Pharm. Bull. 1983, 31, 476
10. Matoba, K.; Terada, T.; Sugiuara, M.; Yamazaki, T. Heterocycles 1987, 26, 55
11. Aftfah, A.; Abu-Shuheil, M. Y.; Hill, J. Tetrahedron 1990, 46, 6483
12. Kumaraswamy, E.; Rees, C. W. Bull. Soc. Chim. Belg. 1997, 106, 605
13. Dieker, J.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2006, 5339
14. Klumpp, D. A.; Zhang, Y.; O'Connor, M. J.; Estevens, P. M.; Almeida, L. S. Org. Lett. 2007, 9, 3085
15. Nakanishi, W.; West, F. G. Curr. Opin. Drug Discovery Dev. 2009, 12 (6) 732
16. Rieder, C. J.; Winberg, K. J.; West, F. G. J. Am. Chem. Soc. 2009, 131, 7504
17. Gaenzler, F. C.; Guo, C. (L.); Zhang, Y.-W.; Azab, M. E.; Salem, M. A. I.; Fan, D. P.; Smith, M. B. Tetrahedron 2009, 65, 8781
18. N -Aminoindoline was prepared from commercially available indoline similar to the procedure described. Smith, A. B., III; Kürti, L.; Davulcu, A. H. Org. Lett. 2006, 8, 2167
19. Neidlein, R.; Feistauer, H. Helv. Chim. Acta 1996, 79, 895
20. Horner, L.; Hoffmann, H.; Wippel, H. G. Chem. Ber. 1958, 91, 61
21. Horner, L.; Hoffmann, H.; Wippel, H. G.; Klahre, G. Chem. Ber. 1959, 92, 2499
22. Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733
23. Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87
24. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73
25. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863
26. 2 values for all reflections. CCDC 816598 (1e) and 816599 (10d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (int.) +44(1223)336-033, E-mail: deposit@ccdc.cam.ac.uk ].
27. Zhu, J.; Zhong, C.; Lu, H.-F.; Li, G.-Y.; Sun, X. Synlett 2008, 3, 458
28. Breit, B.; Winde, R.; Mackewitz, T.; Paciello, R.; Harms, K. Chem.-Eur. J. 2001, 7, 3106
29. Marco, J. L. Synth. Commun. 1996, 26 (22) 4225
30. Satyanarayana, J.; Basaveswara Rao, M. V.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1996, 37 (20) 3565
31. Ferraris, D.; Drury, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568
32. Kobayashi, S.; Busujima, T.; Nagayama, S. Chem.-Eur. J. 2000, 6, 3491
33. Trybulski, E. J.; Benjamin, L. E.; Earley, J. V.; Ian Fryer, R.; Gilman, N. W.; Reeder, E.; Walser, A.; Davidson, A. B.; Dale Horst, W. J. Med. Chem. 1983, 26, 1589
34. Snyder, J. P.; Heyman, M. L.; Gundestrup, M. J. Chem.Soc., Perkin Trans. 1 1977, 13, 1551
35. Wirschun, W. G.; Al-Soud, Y. A.; Nusser, K. A.; Orama, O.; Maier, G.-M.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 2000, 24, 4356
36. Brehme, R.; Nikolajewski, H. E. Z. Chem. 1968, 226
37. Brehme, R.; Enders, D.; Fernandez, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2007, 5629
38. Monge, D.; Martín-Zamora, E.; Vázquez, J.; Alcarazo, M.; Álvarez, E.; Fernández, R.; Lassaletta, J. M. Org. Lett. 2007, 9, 2867
39. Barluenga, J.; Fernandez, A.; Rodriguez, F.; Fananas, F. J. Chem.-Eur. J. 2009, 15, 8121
40. Yeom, H.-S.; Lee, J.-E.; Shin, S. Angew. Chem., Int. Ed. 2008, 47, 7040
41. Mao, H.; Wang, S.; Yu, P.; Lv, H.; Xu, R.; Pan, Y. J. Org. Chem. 2011, 76, 1167
42. Deb, I.; Das, D.; Siedel, D. Org. Lett. 2011, 13, 812
43. Gaussian 09, Revision A.02: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford CT, 2009.
44. 3 complexation at the oxygen atom of 1 is favored by approximately 4 kcal/mol over complexation at either one of the two nitrogen atoms.
45. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
46. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404
47. Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70
48. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297
49. Weigend, F.; Furche, F.; Ahlrichs, R. J. Chem. Phys. 2003, 119 (24) 12753
50. Feller, D. J. Comput. Chem. 1996, 17 (13) 1571
51. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47 (3) 1045
52. Geometry optimizations using the CPCM model failed (no convergence).
53. NBO Version 3.1: Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
54. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211
55. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066
56. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735
57. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736
58. Carpenter, J. E.; Weinhold, F. THEOCHEM 1988, 46, 41
59. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
60. Szekeres, H. J.; Atack, J. R.; Chambers, M. S.; Cook, S. M.; Macaulay, A. J.; Pillai, G. V.; MacLeod, A. M. Bioorg. Med. Chem. Lett. 2004, 14, 2871