Morita-Baylis-Hillman reaction of indole-2-carboxaldehyde: New vistas for indole-annulated systems

Tetrahedron

Volumn 66, Issue 39, 2010, Pages 7781-7786

  Biswas, Subhasish ^a   Singh, Virender ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Heck reaction; Indole 2 carboxaldehyde; Morita Baylis Hillman; RCM; Reductive cyclization

Indexed keywords

ALDEHYDE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 77956394438     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.07.078     Document Type: Article

References (72)

1. Morita, K. Japan Patent 6,803,364, 1968;
2. Chem. Abstr. 69 1968 58828s
3. Baylis, A.B.; Hillman, M.E.D. German Patent 2,155,113, 1972;
4. Chem. Abstr. 77 1972 34174q
5. Only a few citations
6. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48 and references cited therein
7. S. Gowrisankar, H.S. Lee, S.H. Kim, K.Y. Lee, and J.N. Kim Tetrahedron 65 2009 8769 8780
8. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574 and references cited therein
9. D. Basavaiah, K.V. Rao, and R.J. Reddy Chem. Soc. Rev. 36 2007 1581 1588 and references cited therein
10. D. Basavaiah, J.R. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 892
11. D. Basavaiah, B. Devendar, K. Aravindu, and A. Veerendhar Chem. - Eur. J. 16 2010 2031 2035
12. G.W. Amarante, M. Benassi, R.N. Pascoal, M.N. Eberlin, and F. Coelho Tetrahedron 66 2010 4370 4376
13. R. Barth, and W.R. Roush Org. Lett. 12 2010 2342 2345
14. P.R. Krishna, and R.R. Kadiyala Tetrahedron Lett. 51 2010 2586 2588
15. G.W. Amarante, M. Cavallaro, and F. Coelho Tetrahedron Lett. 51 2010 2597 2599
16. D. Basavaiah, and K.R. Reddy Tetrahedron 66 2010 1215 1219
17. V. Singh, S. Hutait, and S. Batra Eur. J. Org. Chem. 19 2010 3684 3691
18. B.A. Trofimov, and N.A. Nedolya A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III 3 2008 Elsevier Oxford 88 167
19. A.J. Kochanowska-Karamyan, and M.T. Hamann Chem. Rev. 110 2010 4489 4497
20. R.J. Sundberg, and S.Q. Smith Alkaloids 59 2002 281 376
21. J.C. Menendez Top. Heterocycl. Chem. 11 2007 63 101
22. S. Suezen Top. Heterocycl. Chem. 11 2007 145 178
23. T. Newhouse, C.A. Lewis, K.J. Eastman, and P.S. Baran J. Am. Chem. Soc. 132 2010 7119 7137
24. S.-M. Li Nat. Prod. Rep. 27 2010 57 78
25. A few citations only
26. G.W. Gribble, M.G. Saulnier, E.T. Pelkey, T.L.S. Kishbaugh, Y.B. Liu, J. Jiang, H.A. Trujillo, D.J. Keavy, D.A. Davis, S.C. Conway, F.L. Switzer, S. Roy, R.A. Silva, J.A. Obaza-Nutaitis, M.P. Sibi, N.V. Moskalev, T.C. Barden, L. Chang, W.M. Habeski, B. Pelcman, W.R. Sponholtz, R.W. Chau, B.D. Allison, S.D. Garaas, M.S. Sinha, M.A. McGowan, M.R. Reese, and K.S. Harpp Curr. Org. Chem. 9 2005 1493 1519
27. G.R. Humphrey, and J.T. Kuethe Chem. Rev. 106 2006 2875 2911
28. S. Cacchi, and G. Fabrizi Chem. Rev. 105 2005 2873 2920
29. P. Thansandote, and M. Lautens Chem. - Eur. J. 15 2009 5874 5883
30. C.A. Baxter, E. Cleator, M. Alam, A.J. Davies, A. Goodyear, and M. O'Hagan Org. Lett. 12 2010 668-671
31. B. Wahab, G. Ellames, S. Passey, and P. Watts Tetrahedron 66 2010 3861 3865
32. R. Sanz, V. Guilarte, and A. Perez Tetrahedron Lett. 50 2009 4423 4426
33. S. Sasaki, T. Yamauchi, and K. Higashiyama Tetrahedron Lett. 51 2010 2326 2328 and references cited therein
34. W. Wang, E. Herdtweckb, and A. Domling Chem. Commun. 46 2010 770 772
35. Z.H. Guan, Z.Y. Yan, Z.H. Ren, X.Y. Liua, and Y.M. Liang Chem. Commun. 46 2010 2823 2825
36. N.R. Candeias, L.C. Branco, P.M.P. Gois, C.A.M. Afonso, and A.F. Trindade Chem. Rev. 109 2009 2703 2802
37. T.J. Donohoe, L.P. Fishlock, and P.A. Procopiou Chem. - Eur. J. 14 2008 5716 5726
38. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, and Y.-C. Chen Angew. Chem., Int. Ed. 48 2009 5737 5740
39. G. Li, X. Huang, and L. Zhang Angew. Chem., Int. Ed. 47 2008 346 349
40. A few recent citations for annulated heterocycles using MBH chemistry from this lab
41. A. Mishra, and S. Batra Eur. J. Org. Chem. 2010 10.1002/ejoc.201000355
42. S. Nag, S. Bhowmik, H.M. Gauniyal, and S. Batra Eur. J. Org. Chem. 2010 10.1002/ejoc.201000586
43. A. Mishra, S. Hutait, S. Bhowmik, N. Rastogi, R. Roy, and S. Batra Synthesis 2010 2731 2748
44. M. Nayak, and S. Batra Tetrahedron Lett. 51 2010 510 516
45. V. Singh, S. Hutait, and S. Batra Eur. J. Org. Chem. 2009 6211 6216
46. S. Nag, M. Nayak, and S. Batra Adv. Synth. Catal. 351 2009 2715 2723
47. V. Singh, S. Hutait, and S. Batra Eur. J. Org. Chem. 2009 3454 3466
48. Friary, R.J.; Kozlowski, J.A.; Shankar, B.B.; Wong, M.K.C.; Zhou, G.; Lavey, B.J.; Shih, N.-Y.; Tong, L.; Chen, L.; Shu, Y. World Patent WO 2,003,042,174, 2003;
49. Chem. Abstr. 138 2003 401607g
50. J.C. McKew, K.L. Lee, M.W.H. Shen, P. Thakker, M.A. Foley, M.L. Behnke, B. Hu, F.-W. Sum, S. Tam, Y. Hu, L. Chen, S.J. Kirincich, R. Michalak, J. Thomason, M. Ipek, K. Wu, L. Wooder, M.K. Ramarao, E.A. Murphy, D.G. Goodwin, L. Albert, X. Xu, F. Donahue, M.S. Ku, J. Keith, C.L. Nickerson-Nutter, W.M. Abraham, C. Williams, M. Hegen, and J.D. Clark J. Med. Chem. 51 2008 3388 3413
51. U. Jacquemard, V. Beneteau, M. Lefoix, S. Routier, J.-Y. Merour, and G. Coudert Tetrahedron 60 2004 10039 10047
52. J.R. Davies, P.D. Kane, C.J. Moody, and A.M.Z. Slawin J. Org. Chem. 70 2005 5840 5851
53. W. Wang, C. Xiong, J. Zhang, and V.J. Hruby Tetrahedron 58 2002 3101 3110
54. O.R. Suarez-Castillo, L.A. Montiel-Ortega, M. Melendez-Rodrguez, and M. Sanchez-Zavala Tetrahedron Lett. 48 2007 17 20
55. A.K. Mohanakrishnan, R. Balamurugan, N. Ramesh, M. Mathiselvam, and S. Manavalan Synth. Commun. 37 2007 4343 4352
56. S.E. Kazzouli, J. Koubachi, S. Berteina-Raboin, A. Mouaddibb, and G. Guillaumet Tetrahedron Lett. 47 2006 8575 8577
57. S. Routier, L. Sauge, N. Ayerbe, G. Coudert, and J.-Y. Merour Tetrahedron Lett. 43 2002 589 591
58. M. Chakrabarty, T. Kundu, and Y. Harigaya Synth. Commun. 36 2006 2069 2077
59. K. Ravinder, A.V. Reddy, K.C. Mahesh, M. Narasimhulu, and Y. Venkateswarlu Synth. Commun. 37 2007 281 287
60. D.K. Mohapatra, and K.A. Durugkar ARKIVOC xiv 2005 20 28
61. G.B. Jones, and C.J. Moody J. Chem. Soc., Perkin Trans. 1 12 1989 2449 2454
62. G.C. Vougioukalakis, and R.H. Grubbs Chem. Rev. 110 2010 1746 1787 and references cited therein
63. S. Monfette, and D.E. Fogg Chem. Rev. 109 2009 3783 3816 and references cited therein
64. K. Wood, D. StC Black, I.N.N. Namboothiri, and N. Kumar Tetrahedron Lett. 51 2010 1606 1608
65. M.-L. Bennasar, E. Zulaica, and S. Tummers Tetrahedron Lett. 45 2004 6283 6285
66. P. Evans, R. Grigg, and M. York Tetrahedron Lett. 41 2000 3967 3970
67. P.-Y. Chen, H.-M. Chen, L.-Y. Chen, J.-Y. Tzeng, J.-C. Tsai, P.-C. Chi, S.-R. Lic, and E.-C. Wanga Tetrahedron 63 2007 2824 2828
68. Y.-Q. Ge, J. Jia, H. Yang, G.-L. Zhao, F.-X. Zhan, and J. Wang Heterocycles 78 2009 725 736
69. Y.-Q. Ge, J. Jia, Y. Li, L. Yin, and J. Wang Heterocycles 78 2009 197 206
70. T.L. Gilchrist, P.D. Kemmitt, and A.L. Germain Tetrahedron 53 1997 4447 4456
71. J.A. Brekan, T.E. Reynolds, and K.A. Scheidt J. Am. Chem. Soc. 132 2010 1472 1473
72. Y. Murakami, N. Imai, T. Miura, T. Sugimura, K. Wakabayashi, Y. Totsuka, N. Hada, Y. Yokoyama, H. Suzuki, and K. Mitsunaga Heterocycles 80 2010 455 462