Synthesis of indolyl imidazole derivatives via base-promoted tandem reaction of N-[2-(1-alkynyl)phenyl]carbodiimides with isocyanides

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3634-3640

  Hao, Wenyan ^a   Jiang, Yuanyuan ^a   Cai, Mingzhong ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

CARBODIIMIDES; IMIDAZOLE DERIVATIVES; ISOCYANIDES; TANDEM PROCESS; TANDEM REACTION;

CYANIDES;

BASE; CYANAMIDE; CYANIDE; DIMETHYL SULFOXIDE; IMIDAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; CYCLOADDITION; ISOMERIZATION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

CARBODIIMIDES; CYANIDES; DIMETHYL SULFOXIDE; IMIDAZOLES; INDOLES; MOLECULAR STRUCTURE;

EID: 84899008660     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402552c     Document Type: Article

References (93)

1. Sundberg, R. J. In The Chemistry of Indoles; Academic Press, New York, 1970.
2. Brown, R. K. In Indoles; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972.
3. Sharma, V.; Kumar, P. D. J. Heterocycl. Chem. 2010, 47, 491
4. Kaushik, N. K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C. H.; Verma, A. K.; Choi, E. H. Molecules 2013, 18, 6620
5. Marco, B.; Astrid, E. Angew. Chem., Int. Ed. 2009, 48, 9608
6. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195
7. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Org. React. 2012, 76, 281
8. Fischer, E.; Jourdan, F. Chem. Ber. 1883, 16, 2241
9. Hegedus, L. S.; Allen, G. F.; Olsen, D. J. J. Am. Chem. Soc. 1980, 102, 3583
10. Kondo, Y.; Sakamoto, T.; Yamanaka, H. Heterocycles 1989, 48, 1013
11. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689
12. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652
13. Yasuhara, A.; Kaneko, M.; Sakamoto, T. Heterocycles 1998, 48, 1793
14. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671
15. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Adv. Synth. Catal. 2006, 348, 130
16. Lu, B. Z.; Zhao, W.; Wei, H.-X.; Dufour, M.; Farina, V.; Senanayake, C. H. Org. Lett. 2006, 8, 3271
17. Han, X.; Lu, X. Org. Lett. 2010, 12, 3336
18. álvarez, R.; Mart́nez, C.; Madich, Y.; Denis, J. G.; Aurrecoechea, J. M.; de Lera, A. R. Chem. - Eur. J. 2010, 16, 12746
19. Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew. Chem., Int. Ed. 2007, 46, 2295
20. Ohta, Y.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 7052
21. Ohta, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 1979
22. Cai, Q.; Li, Z.; Wei, J.; Ha, C.; Pei, D.; Ding, K. Chem. Commun. 2009, 7581
23. Chen, Z.; Zheng, D.; Wu, J. Org. Lett. 2011, 13, 848
24. Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org. Lett. 2010, 12, 3736
25. Nguyen, Q.; Nguyen, T.; Driver, T. G. J. Am. Chem. Soc. 2013, 135, 620
26. Stokes, B. J.; Dong, H.; Leslie, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500
27. Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem., Int. Ed. 2008, 47, 5056
28. Stokes, B. J.; Richert, K. J.; Driver, T. G. J. Org. Chem. 2009, 74, 6442
29. Sun, K.; Liu, S.; Bec, P. M.; Driver, T. G. Angew. Chem., Int. Ed. 2011, 50, 1702
30. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702
31. Jordaan, A.; Arndt, R. R. J. Heterocycl. Chem. 1968, 5, 723
32. Abu Safieh, K. A.; Darras, F. H.; Ayoub, M. T.; El-Abadelah, M. M.; Sabri, S. S.; Voelter, W. Heterocycles 2007, 71, 2681
33. Pidlypnyi, N.; Uhrner, F.; Nieger, M.; Drafz, M. H. H.; Huebner, E. G.; Namyslo, J. C.; Schmidt, A. Eur. J. Org. Chem. 2013, 34, 7739
34. Lipshutz, B. H.; Vaccaro, W.; Huff, B. Tetrahedron Lett. 1986, 27, 4095
35. Lipshutz, B. H.; Huff, B.; Hagen, W. Tetrahedron Lett. 1988, 29, 3411
36. Lipshutz, B. H.; Hagen, W. Tetrahedron Lett. 1992, 33, 5865
37. Delest, B.; Nshimyumukiza, P.; Fasbender, O.; Tinant, B.; Marchand-Brynaert, J.; Darro, F.; Robiette, R. J. Org. Chem. 2008, 73, 6816
38. Joo, J. M.; Tour, B. B.; Sames, D. J. Org. Chem. 2010, 75, 4911
39. Shibahara, F.; Yamauchi, T.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2012, 77, 8815
40. Lipshutz, B. H. Chem. Rev. 1986, 86, 795
41. Schnrch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283
42. Du, H.; He, Y.; Sivappa, R.; Lovely, C. J. Synlett 2006, 7, 965
43. Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200
44. Bellina, F.; Rossi, R. Adv. Synth. Catal. 2010, 352, 1223
45. Zheng, D.; Li, S.; Luo, Y.; Wu, J. Org. Lett. 2011, 13, 6402
46. Qiu, G.; Wu, J. Chem. Commun. 2012, 48, 6046
47. Zheng, D.; Li, S.; Wu, J. Chem. Commun. 2012, 48, 8568
48. Zheng, D.; Li, S.; Wu, J. Org. Lett. 2012, 14, 2655
49. Li, S.; Wu, J. Chem. Commun. 2012, 48, 8973
50. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168
51. Suginome, M.; Ito, Y. In Science of Synthesis; Murahashi, S.-I., Ed.; Thieme: Stuttgart, 2004; Vol. 19, p 445.
52. Dömling, A. Chem. Rev. 2006, 106, 17
53. Lygin, A. V.; Meijere, A. D. Angew. Chem., Int. Ed. 2010, 49, 9094
54. Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235
55. Schöllkopf, U. Angew. Chem., Int. Ed. 1977, 16, 339
56. Takaya, H.; Kojima, S.; Murahashi, S. Org. Lett. 2001, 3, 421
57. Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664
58. Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260
59. Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2006, 128, 10662
60. Benito-Garagorri, D.; Bocokiae, V.; Kirchner, K. Tetrahedron Lett. 2006, 47, 8641
61. Bonin, M.-A.; Giguere, D.; Roy, R. Tetrahedron 2007, 63, 4912
62. Lygin, A. V.; Larionov, O. V.; Korotkov, V. S.; de Meijere, A. Chem. - Eur. J. 2009, 15, 227
63. Zhou, H.; Zhang, W.; Yan, B. J. Comb. Chem. 2010, 12, 206
64. Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. Soc. 2011, 133, 1775
65. Monge, D.; Jensen, K. L.; Marín, I.; Jørgensen, K. A. Org. Lett. 2011, 13, 328
66. Cai, Q.; Tao, Z.; Xu, T.; Fu, L.; Ding, K. Org. Lett. 2011, 13, 340
67. Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 3633
68. Fayol, A.; Zhu, J. Org. Lett. 2004, 6, 115
69. Bonne, D.; Dekhane, M.; Zhu, J. Angew. Chem., Int. Ed. 2006, 45, 2485
70. Fayol, A.; Zhu, J. Org. Lett. 2007, 7, 239
71. Wang, S.; Wang, M.; Wang, D.; Zhu, J. Org. Lett. 2007, 9, 3615
72. Yue, T.; Wang, M.; Wang, D.; Masson, G.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 6717
73. Mossetti, R.; Pirali, T.; Tron, G. C.; Zhu, J. Org. Lett. 2010, 12, 820
74. Lalli, C.; Bouma, M. J.; Bonne, D.; Masson, G.; Zhu, J. Chem. - Eur. J. 2011, 17, 880
75. Khorana, H. G. Chem. Rev. 1953, 67, 145
76. Kurzer, F.; Douraghi-Zadeh, K. Chem. Rev. 1967, 67, 107
77. Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589
78. Schmittel, M.; Steffen, J.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. 1998, 37, 2371
79. Li, H.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2003, 68, 5512
80. Zhang, W.; Nishiura, M.; Hou, Z. J. Am. Chem. Soc. 2005, 127, 1678
81. Shen, H.; Chan, H.-S.; Xie, Z. Organometallics 2006, 25, 5515
82. Saito, T.; Sugizaki, K.; Otani, T.; Suyama, T. Org. Lett. 2007, 9, 1239
83. Zhang, W.; Nishiura, M.; Hou, Z. Chem. - Eur. J. 2007, 13, 4037
84. Zhang, W.; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720
85. Wang, Y.; Chi, Y.; Zhang, W.; Wang, Z.; Xi, Z. J. Am. Chem. Soc. 2012, 134, 2926
86. Hoogenboom, B. E.; Oldenziel, O. H.; Van Leusen, A. M. Org. Synth. 1977, 57
87. Ten Have, R.; Leusink, F. R.; Van Leusen, A. M. Synthesis 1996, 7, 871
88. Ten Have, R.; Huisman, M.; Meetsma, A.; Van Leusen, A. M. Tetrahedron 1997, 53, 11355
89. Van Leusen, A. M.; Van Leusen, D. e-EROS Encycl. Reagents Org. Synth. 2001, 10.1002/047084289X.rd197
90. Van Leusen, D.; Van Leusen, A. M. Org. React. 2001, 57, 417
91. Van Leusen, A. M.; Van Leusen, D.; Czako, B. e-EROS Encycl. Reagents Org. Synth. 2007, 10.1002/047084289X.rt150.pub2
92. Saito, T.; Shiotani, M.; Otani, T.; Hasaba, S. Heterocycles 2003, 60, 1045
93. Schmittel, M.; Steffen, J.-P.; Rodríguez, D.; Engelen, B.; Neumann, E.; Emin Cinar, M. J. Org. Chem. 2008, 73, 3005