Microwave-assisted facile synthesis of [a]-annelated pyrazolopyrroloindoles via intramolecular azomethine imine 1,3-dipolar cycloaddition

Tetrahedron Letters

Volumn 55, Issue 19, 2014, Pages 3064-3069

  Shinde, Anand H ^a   Vidyacharan, Shinde ^a   Sharada, Duddu S ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY HYDERABAD   (India)

Author keywords

1,3 Dipolar cycloaddition; Azomethine imine; Microwave assisted; Pyrazolopyrroloindole; Stereoselective

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRAZOLOPYRROLOINDOLE DERIVATIVE; UNCLASSIFIED DRUG; IMINE;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION TIME; COLUMN CHROMATOGRAPHY; MICROWAVE RADIATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84899621920     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.03.134     Document Type: Article

References (70)

1. C.R. Kodihalli, M.V. Hosadu, and V.P. Vaidya ARKIVOC xi 2008 1
2. M.N. Kumaraswamy, C. Chandrashekhar, H. Shivakumar, D.A. Prathima Mathias, K.M. Mahadevan, and V.P. Vaidya Indian J. Pharm. Sci. 70 2008 715
3. For a seminal review on pyrrolo[1,2-a]indoles, see: W. Verboom, and D.N. Reinhoudt Recl. Trav. Chim. Pays-Bas 105 1986 199
4. For recent syntheses of pyrrolo[1,2-a]indoles, see: D.V. Patil, M.A. Cavitt, and S. France Org. Lett. 13 2011 5820
5. L. Li, D. Du, J. Ren, and Z. Wang Eur. J. Org. Chem. 2011 614
6. H.-Y. Pyeon, S.-H. Pyo, J.-K. Ahn, and G.-C. Kim Bull. Korean Chem. Soc. 2011 735
7. D.M. Schultz, and J.P. Wolfe Org. Lett. 12 2010 1028
8. W. He, K.-T. Yip, N.-Y. Zhu, and D. Yang Org. Lett. 11 2009 5626
9. D. Enders, C. Wang, and G. Raabe Synthesis 2009 4119
10. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, and Y.-C. Chen Angew. Chem., Int. Ed. 48 2009 5737
11. D.H. Dethe, R.D. Erande, and A. Ranjan J. Am. Chem. Soc. 133 2011 2864
12. L.S. Fernandez, M.S. Buchanan, A.R. Carroll, Y.J. Feng, R.J. Quinn, and V.M. Avery Org. Lett. 11 2009 329
13. S.E. Wolkenberg, and D.L. Boger Chem. Rev. 102 2002 2477
14. J.-F. Liu, Z.-Y. Jiang, R.-R. Wang, Y.-T. Zheng, J.-J. Chen, X.-M. Zhang, and Y.-B. Ma Org. Lett. 9 2007 4127
15. J.J. Vepsalainen, S. Auriola, M. Tukiainen, N. Ropponen, and J.C. Callaway Planta Med. 71 2005 1053
16. A. Padwa 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York, NY
17. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev. 106 2006 4484
18. I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765
19. Y. Kong, M. Tang, and Y. Wang Org. Lett. 16 2014 576
20. J.M. Lopchuk, R.P. Hughes, and G.W. Gribble Org. Lett. 15 2013 5218
21. V.Y. Korotaev, A.Y. Barkov, V.S. Moshkin, E.G. Matochkina, M.I. Kodess, and V.Y. Sosnovskikh Tetrahedron 69 2013 8602
22. J. Takaya, Y. Miyashita, H. Kusama, and N. Iwasawa Tetrahedron 67 2011 4455
23. J. Pospíšil, and M. Potáček Tetrahedron 63 2007 337
24. L.-L. Xu, C.-J. Zheng, L.-P. Sun, J. Miao, and H.-R. Piao Eur. J. Med. Chem. 48 2012 174
25. I. Vujasinovic, A. Paravic-Radicevic, K. Mlinaric-Majerski, K. Brajsa, and B. Bertosa Bioorg. Med. Chem. 20 2012 2101
26. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, and J. Yamagishi J. Med. Chem. 47 2004 3693
27. A. Geronikaki, E. Babaev, J. Dearden, W. Dehaen, D. Filimonov, I. Galaeva, V. Krajneva, A. Lagunin, F. Macaev, G. Molodavkin, V. Poroikov, S. Pogrebnoi, V. Saloutin, A. Stepanchikova, E. Stingaci, N. Tkach, L. Vlad, and T. Voronina Bioorg. Med. Chem. 12 2004 6559
28. G. Theodoridis Modern Crop Protection Compounds W. Krämer, U. Schirmer, vol. 1 2007 Wiley-VCH Weinheim, Germany 153
29. Y. Shiga, I. Okada, Y. Ikeda, E. Takizawa, and T. Fukuchi J. Pestic. Sci. 28 2003 313
30. L.A. Sviridova, G.A. Golubeva, A.N. Tavtorkin, and K.A. Kochetkov Amino Acids 43 2012 1225
31. S.A.J. Lang, and Y.I. Lin Comprehensive Heterocyclic Chemistry A.R. Katritzky, C.W. Rees, vol. 6 1984 Pergamon Oxford
32. K. Kotera, Y. Takano, A. Matsuura, and K. Kitahonoki Tetrahedron 26 1970 539
33. S.K. Mishra, P. Majumdar, R.K. Behera, and A.K. Behera Synth. Commun. 44 2014 32
34. G. Zhang, H. Ni, W. Chen, J. Shao, H. Liu, B. Chen, and Y. Yu Org. Lett. 15 2013 5967
35. S. Arepally, and R. Nagarajan Synthesis 45 2013 1235
36. S.H. Kim, J.W. Lim, J. Yu, and J.N. Kim Bull. Korean Chem. Soc. 34 2013 2915
37. D. Verma, S.M. Mobin, and I.N.N. Namboothiri J. Org. Chem. 76 2011 4764
38. A.R. Martin, K. Mohanan, L. Toupet, J.J. Vasseur, and M. Smietana Eur. J. Org. Chem. 2011 3184
39. R. Muruganantham, and I.N.N. Namboothiri J. Org. Chem. 75 2010 2197
40. K. Mohanan, A.R. Martin, L. Toupet, M. Smietana, and J. Vasseur Angew. Chem., Int. Ed. 49 2010 3196
41. J.-W. Xie, Z. Wang, W.-J. Yang, L.-C. Kong, and D.-C. Xu Org. Biomol. Chem. 7 2009 4352
42. R. Muruganantham, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 9 2007 1125
43. R. Na, H. Liu, Z. Li, B. Wang, J. Liu, M.A. Wang, M. Wang, J. Zhong, and H. Guo Tetrahedron 68 2012 2349
44. D.K. Maiti, N. Chatterjee, P. Pandit, and S.K. Hota Chem. Commun. 2010 2022
45. X. Deng, and N.S. Mani J. Org. Chem. 73 2008 2412
46. K.M. Dawood, and T. Fuchigami J. Org. Chem. 70 2005 7537
47. G. Molteni, and A. Ponti Chem. Eur. J. 9 2003 2770
48. B. Liu, M. Wang, and Z. Huang Tetrahedron Lett. 40 1999 7399
49. J.L. Valle, C. Polo, T. Torroba, and S. Marcaccini J. Heterocycl. Chem. 32 1995 899
50. M. Nayak, N. Rastogi, and S. Batra Tetrahedron 69 2013 5029
51. Y. Li, Y. Meng, X. Mengand, and Z. Li Tetrahedron 67 2011 4002
52. W. Oppolzer Tetrahedron Lett. 11 1970 3091
53. W. Oppolzer Angew. Chem., Int. Ed. Engl. 16 1977 10
54. D. Helene, S. Guerrand, H. Adams, and I. Coldham Org. Biomol. Chem. 9 2011 7921
55. J. Galeta, S. Man, J.-P. Bouillon, and M. Potacek Eur. J. Org. Chem. 2011 392
56. H. Ren, S. Ye, F. Liu, and J. Wu Tetrahedron 66 2010 8242
57. S. Ye, X. Yang, and J. Wu Chem. Commun. 2010 5238
58. J.J. Neumann, M. Suri, and F. Glorius Angew. Chem., Int. Ed. 49 2010 7790
59. T. Hashimoto, H. Kimura, Y. Kawamata, and K. Maruoka Nat. Chem. 3 2011 642
60. T. Hashimoto, Y. Maeda, M. Omote, H. Nakatsu, and K. Maruokajacs J. Am. Chem. Soc. 132 2010 4076
61. S. Kanemasa, N. Tomoshige, E. Wada, and O. Tsuge Bull. Chem. Soc. Jpn 62 1989 3944
62. A. Loupy Microwaves in Organic Synthesis 2nd ed. 2006 Wiley-VCH Weinheim, Germany
63. J.D. Moseley, and C.O. Kappe Green Chem. 13 2011 794
64. C.O. Kappe Chem. Soc. Rev. 37 2008 1127
65. D. Prajapati, and S. Gadhwal Tetrahedron 60 2004 4909
66. Y. Zhu, S. Wen, G. Yin, D. Hong, P. Lu, and Y. Wang Org. Lett. 13 2011 3553
67. M. Srivastava, P. Rai, J. Singh, and J. Singh J. New Chem. 38 2014 302
68. E.T. Kool, D.-H. Park, and P. Crisalli J. Am. Chem. Soc. 135 2013 17663
69. B.M. Anderson, and W.P. Jencks J. Am. Chem. Soc. 82 1960 1773
70. For similar kind of autoxidation see: B. Sun, K. Adachi, and Noguchi Tetrahedron 52 1996 901