Solvent-Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles

Chemistry - A European Journal

Volumn 20, Issue 41, 2014, Pages 13217-13225

  Mo, Dong Liang ^a   Wink, Donald J ^a   Anderson, Laura L ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Cascade reaction; dihydrocarbazole; dihydropyridoindole; nitrone; solvent effect

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBONS; SOLVENTS; SYNTHESIS (CHEMICAL);

CASCADE REACTIONS; DIHYDROCARBAZOLE; DIHYDROPYRIDOINDOLE; NITRONES; SOLVENT EFFECTS;

PROCESS CONTROL;

EID: 84941049203     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403268     Document Type: Article

References (87)

1. K. M. G. O'Connell, W. R. J. D. Galloway, D. R. Spring, The Basics of Diversity-Oriented Synthesis. In, Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis Drug Discovery, and Chemical Biology, 1ed st ed(Ed.:, A. Trabocchi,), Wiley, Hoboken, 2013, pp. 1-26;
2. R. J. Spandl, M. Díaz-Gavilán, K. M. G. O'Connel, G. L. Thomas, D. R. Spring, Chem. Rec. 2008, 8, 129;
3. C. J. O'Connor, H. S. G. Beckmann, D. R. Spring, Chem. Soc. Rev. 2012, 41, 4444;
4. W. R. J. D. Galloway, A. Isidro-Llobet, D. R. Spring, Nat. Commun. 2010, 1, 80.
5. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
6. Angew. Chem. Int. Ed. 2006, 45, 7134;
7. A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341;
8. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993;
9. L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc. Chem. Res. 2012, 45, 1278;
10. F.-Z. Peng, Z.-H. Shao, Curr. Org. Chem. 2011, 15, 4144.
11. For a review of diversity-oriented natural product synthesis that includes examples of reagent-, substrate-, and catalyst-controlled cascade reactions, see:, C. Serba, N. Winssinger, Eur. J. Org. Chem. 2013, 4195.
12. V. A. Ignatenko, G. P. Tochtrop, J. Org. Chem. 2013, 78, 3821;
13. X. Zhang, X. Song, H. Li, S. Zhang, X. Chen, X. Yu, W. Wang, Angew. Chem. 2012, 124, 7394;
14. Angew. Chem. Int. Ed. 2012, 51, 7282;
15. S. Santra, P. R. Andreana, Angew. Chem. 2011, 123, 9590;
16. Angew. Chem. Int. Ed. 2011, 50, 9418;
17. Y. Zhang, S. Wang, S. Wu, S. Zhu, G. Dong, Z. Miao, J. Yao, W. Zhang, C. Sheng, W. Wang, ACS Comb. Sci. 2013, 15, 298;
18. H.-G. Cheng, C.-B. Chen, F. Tan, N.-J. Chang, J.-R. Chen, W.-J. Xiao, Eur. J. Org. Chem. 2010, 4976;
19. D. Robbins, A. F. Newton, C. Gignoux, J. C. Legeay, A. Sinclair, M. Rejzek, C. A. Laxon, S. K. Yalamanchili, W. Lewis, M. A. O'Connell, R. A. Stockman, Chem. Sci. 2011, 2, 2232;
20. R. Halim, L. Aurelio, P. J. Scammells, B. L. Flynn, J. Org. Chem. 2013, 78, 4708;
21. M. Díaz-Gavilán, W. R. J. D. Galloway, K. M. G. O'Connell, J. T. Hodkingson, D. R. Spring, Chem. Commun. 2010, 46, 776;
22. G. Valot, J. Garcia, V. Duplan, C. Serba, S. Barluenga, N. Winssinger, Angew. Chem. 2012, 124, 5487;
23. Angew. Chem. Int. Ed. 2012, 51, 5391;
24. B. R. Balthaser, M. C. Maloney, A. B. Beeler, J. A. Porco, Jr., J. K. Snyder, Nat. Chem. 2011, 3, 969;
25. N. T. Patil, A. Konala, S. Sravanti, A. Singh, R. Ummanni, B. Sridhar, Chem. Commun. 2013, 49, 10109;
26. A. Shakoori, J. B. Bremmer, A. C. Willis, R. Haritakun, P. A. Keller, J. Org. Chem. 2013, 78, 7639;
27. W. Liu, V. Khedkar, B. Baskar, M. Schürmann, K. Kumar, Angew. Chem. 2011, 123, 7032;
28. Angew. Chem. Int. Ed. 2011, 50, 6900;
29. H. Waldmann, M. Kühn, W. Liu, K. Kumar, Chem. Commun. 2008, 1211.
30. D.-L. Mo, L. L. Anderson, Angew. Chem. 2013, 125, 6854;
31. Angew. Chem. Int. Ed. 2013, 52, 6722.
32. For examples of biologically active, partially saturated carbazoles and pyrido[1,2-a]indoles, see:
33. S. Yokoshima, T. Ueda, S. Kobayashi, A. Sato, T. Kuboyama, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 2137;
34. D. B. C. Martin, L. Q. Nguyen, C. D. Vanderwal, J. Org. Chem. 2012, 77, 17;
35. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183;
36. D. Kato, Y. Sasaki, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 3685;
37. Y. Sasaki, D. Kato, D. L. Boger, J. Am. Chem. Soc. 2010, 132, 13533;
38. D. C. Rogness, N. A. Markina, J. P. Waldo, R. C. Larock, J. Org. Chem. 2012, 77, 2743;
39. I. Jirkovsky, G. Santroch, R. Baudy, G. Oshiro, J. Med. Chem. 1987, 30, 388;
40. O. Khdour, E. B. Skibo, J. Org. Chem. 2007, 72, 8636.
41. B. J. Albert, H. Yamamoto, Angew. Chem. 2010, 122, 2807;
42. Angew. Chem. Int. Ed. 2010, 49, 2747;
43. M. Xia, G.-F. Xiang, B. Wu, Y.-F. Han, Adv. Synth. Catal. 2008, 350, 817.
44. M. Hesse, Alkaloids, Nature's Curse or Blessing, Wiley-VCH, New York, 2002;
45. J. Bosch, J. Bonjoch, M. Amat, in The Alkaloids (Ed.:, G. A. Cordell,), Academic Press, New York, 1996, Vol. 48, pp. 75-189;
46. A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193;
47. W. Maneerat, T. Ritthiwigrom, S. Cheenpracha, T. Promgool, K. Yossathera, S. Deachathai, W. Phakhode, S. Laphookhieo, J. Nat. Prod. 2012, 75, 741;
48. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045;
49. C. R. Edwankar, R. V. Edwankar, O. A. Namjoshi, S. K. Rallapappi, S. J. Yang, J. M. Cook, Curr. Opin. Drug Discovery Dev. 2009, 12, 752;
50. D. F. Taber, P. K. Tirunahari, Tetrahedron 2011, 67, 7195.
51. C. S. Shanahan, P. Truong, S. M. Mason, J. S. Leszczynski, M. P. Doyle, Org. Lett. 2013, 15, 3642;
52. M. Hussain, S.-M. T. Toguem, R. Ahmad, D. T. Tùng, I. Knepper, A. Villinger, P. Langer, Tetrahedron 2011, 67, 5304;
53. F. Inagaki, M. Mizutani, N. Kuroda, C. Mukai, J. Org. Chem. 2009, 74, 6402;
54. N. Kuroda, Y. Takahashi, K. Yoshinaga, C. Mukai, Org. Lett. 2006, 8, 1843;
55. C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358;
56. R. A. Jones, P. M. Fresneda, T. A. Saliente, J. S. Arques, Tetrahedron 1984, 40, 4837;
57. C. Exon, T. Gallagher, P. Magnus, J. Chem. Soc. Chem. Commun. 1982, 613.
58. 2 was excluded from the reaction of 3 n with 4 a to minimize competing hydrolysis of the aldehyde-derived nitrone.
59. See Supporting Information for copper-mediated nitrone synthesis. See the following for related examples of CN bond coupling to form nitrones:, D.-L. Mo, D. J. Wink, L. L. Anderson, Org. Lett. 2012, 14, 5180 and ref. [5].
60. J. Wilkens, A. Kühling, S. Blechert, Tetrahedron 1987, 43, 3237;
61. A. Padwa, W. H. Bullock, D. N. Kline, J. Perumattam, J. Org. Chem. 1989, 54, 2862;
62. T. Wirth, S. Blechert, Synlett 1994, 717.
63. A. Padwa, S. P. Carter, Y. Chiacchio, D. N. Kline, Tetrahedron Lett. 1986, 27, 2683;
64. A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909;
65. A. Padwa, M. Matzinger, Y. Tomioka, M. K. Venkatramanan, J. Org. Chem. 1988, 53, 955.
66. S. P. Modi, A. H. Zayed, S. Archer, J. Org. Chem. 1989, 54, 3084;
67. M. L. Bennasar, M. Alvarez, R. Lavilla, E. Zulaica, J. Bosch, J. Org. Chem. 1990, 55, 1156;
68. J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
69. J. Zhou, M.-C. Ye, Z.-Z. Huang, Y. Tang, J. Org. Chem. 2004, 69, 1309;
70. J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030.
71. 4 to prevent hydrolysis of the aldehyde-derived nitrones.
72. M. Takemoto, Y. Iwakiri, Y. Suzuki, K. Tanaka, Tetrahedron Lett. 2004, 45, 8061;
73. F. Sigaut, J. Levy, Tetrahedron Lett. 1989, 30, 2937;
74. J. L. Rogers, J. B. MacMillan, J. Am. Chem. Soc. 2012, 134, 12378;
75. C. A. Mateo, A. Urrutia, J. G. Rodriguez, I. Fonseca, F. H. Cano, J. Org. Chem. 1996, 61, 810;
76. D. Stoermer, C. H. Heathcock, J. Org. Chem. 1993, 58, 564.
77. M. P. S. Ishar, K. Kumar, Tetrahedron Lett. 1999, 40, 175;
78. A. Kapur, K. Kumar, L Singh, P. Singh, M. Elango, V. Subramanian, V. Gupta, P. Kanwal, M. P. S. Ishar, Tetrahedron 2009, 65, 4593.
79. C. F. Gürtler, S. Blechert, E. Steckhan, Chem. Eur. J. 1997, 3, 447;
80. H. Li, N. Boonnak, A. Padwa, J. Org. Chem. 2011, 76, 9488;
81. S. Chitra, N. Paul, S. Muthusubramanian, P. Manisankar, Green Chem. 2011, 13, 2777.
82. Less than 5 % 1 a-1 n were separated during purification of 2 a-2 n indicating that the 2: 1 ratios for all of these reactions were greater than or equal to 10:1.
83. Less than 5 % 1 o-1 x, 1 bb were separated during purification of 2 o-2 x, 2 bb indicating that the 2: 1 ratios for all of these reactions were greater than or equal to 10:1.
84. Less than 5 % 6-8 were separated during purification of 25-27 and less than 5 % of the corresponding dihydrocarbazoles were separated from 28-32 indicating that the 2: 1 ratios for all of these reactions were greater than or equal to 10:1.
85. Irrespective of the reaction media, amide substitution on the allene strongly favors the formation of dihydropyridoindoles, and mixtures of 1 and 2 were even observed when these reagents were subjected to toluene-mediated reaction conditions previously optimized for dihydrocarbazole synthesis.
86. For examples of 1,4-additions of β-diesters to α,β-unsaturated imines, see:, F. Palacios, A. M. Ochoa de Retana, S. Pascual, G. Fernández de Trocõniz, J. M. Ezpeleta, Eur. J. Org. Chem. 2010, 6618.
87. 1H NMR spectrum. Dihydrocarbazoles 1 that have been prepared from ketone-derived nitrones are stable in air at 25 °C and only begin to oxidize slowly to the corresponding carbazoles at higher temperatures (5-10 % after 18 h at 80 °C). Dihydrocarbazoles 1 that have been prepared from aldehyde-derived nitrones are stable at -40 °C but slowly oxidize at 25 °C in air and more quickly at higher temperatures (∼50 % after 18 h at 80 °C). Dihydropyridoindoles 2 show no sign of oxidation when heated in air for 18 h at 80 °C.