Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides

Organic Letters

Volumn 17, Issue 19, 2015, Pages 4750-4753

  Zhan, Gu ^a   Shi, Ming Lin ^a   He, Qing ^a   Du, Wei ^a   Chen, Ying Chun ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b THIRD MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CHLORINATED HYDROCARBON; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; ISATIN; LEWIS BASE; OXINDOLE; SPIRO COMPOUND;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

AMIDES; CATALYSIS; CYCLOADDITION REACTION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, CHLORINATED; INDOLES; ISATIN; LEWIS BASES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS;

EID: 84942894368     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02279     Document Type: Article

References (69)

1. Harmata, M. Adv. Synth. Catal. 2006, 348, 2297 10.1002/adsc.200600294
2. Jones, D. E.; Harmata, M. Methods and Applications of Cycloaddition Reactions in Organic Syntheses; Nishiwaki, N., Eds; John Wiley & Sons: Hoboken, NJ, 2014; pp 599-630.
3. Harmata, M. Chem. Commun. 2010, 46, 8886 10.1039/c0cc03620j
4. Harmata, M. Chem. Commun. 2010, 46, 8904 10.1039/c0cc03621h
5. Lohse, A. G.; Hsung, R. P. Chem.-Eur. J. 2011, 17, 3812 10.1002/chem.201100260
6. Chung, W. K.; Lam, S. K.; Lo, B.; Liu, L. L.; Wong, W.-T.; Chiu, P. J. Am. Chem. Soc. 2009, 131, 4556 10.1021/ja807566t
7. Lo, B.; Chiu, P. Org. Lett. 2011, 13, 864 10.1021/ol102897d
8. Lam, S.; Lo, B.; Wong, W.-T.; Chiu, P. Asian J. Org. Chem. 2012, 1, 30 10.1002/ajoc.201200038
9. Lo, B.; Lam, S.; Wong, W.-T.; Chiu, P. Angew. Chem., Int. Ed. 2012, 51, 12120 10.1002/anie.201207427
10. Lam, S. K.; Lam, S.; Wong, W.-T.; Chiu, P. Chem. Commun. 2014, 50, 1738 10.1039/c3cc48266a
11. Lv, H.; Jia, W.-Q.; Sun, L.-H.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 8607 10.1002/anie.201303903
12. Guo, C.; Sahoo, B.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2014, 136, 17402 10.1021/ja510737n
13. Liu, K.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2014, 16, 4508 10.1021/ol5020569
14. Hu, X.-Q.; Chen, J.-R.; Gao, S.; Feng, B.; Lu, L.-Q.; Xiao, W.-J. Chem. Commun. 2013, 49, 7905 10.1039/c3cc43888k
15. Li, Z.; Yu, H.; Feng, Y.; Hou, Z.; Zhang, L.; Yang, W.; Wu, Y.; Xiao, Y.; Guo, H. RSC Adv. 2015, 5, 34481 10.1039/C5RA04374C
16. Xu, H.; Hu, J.-L.; Wang, L.; Liao, S.; Tang, Y. J. Am. Chem. Soc. 2015, 137, 8006 10.1021/jacs.5b04429
17. Hu, J.-L.; Wang, L.; Xu, H.; Tang, Y. Org. Lett. 2015, 17, 2680 10.1021/acs.orglett.5b01077
18. Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244 10.1021/ja803890t
19. Shu, D.; Song, W.; Li, X.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 3237 10.1002/anie.201209266
20. Guzmán, P. E.; Lian, Y.; Davies, H. M. L. Angew. Chem., Int. Ed. 2014, 53, 13083 10.1002/anie.201406440
21. Liu, T.-Y.; Xie, M.; Chen, Y.-C. Chem. Soc. Rev. 2012, 41, 4101 10.1039/c2cs35017c
22. Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659 10.1021/cr300192h
23. Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578 10.1039/C5OB00865D
24. Du, Y.; Lu, X.; Zhang, C. Angew. Chem., Int. Ed. 2003, 42, 1035 10.1002/anie.200390266
25. Feng, J.; Lu, X.; Kong, A.; Han, X. Tetrahedron 2007, 63, 6035 10.1016/j.tet.2007.02.115
26. Zheng, S.; Lu, X. Org. Lett. 2008, 10, 4481 10.1021/ol801661y
27. Selvakumar, K.; Vaithiyanathan, V.; Shanmugam, P. Chem. Commun. 2010, 46, 2826 10.1039/b924066g
28. Wang, Q.-G.; Zhu, S.-F.; Ye, L.-W.; Zhou, C.-Y.; Sun, X.-L.; Tang, Y.; Zhou, Q.-L. Adv. Synth. Catal. 2010, 352, 1914 10.1002/adsc.201000129
29. Deng, H. P.; Wei, Y.; Shi, M. Org. Lett. 2011, 13, 3348 10.1021/ol201094f
30. Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837 10.1002/anie.201102094
31. Tan, B.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2011, 133, 4672 10.1021/ja110147w
32. Wang, D.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 2764 10.1039/c2cc17709a
33. Zhong, F.; Chen, G.; Han, X.; Yao, W.; Lu, Y. Org. Lett. 2012, 14, 3764 10.1021/ol301647g
34. Deng, H.-P.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2012, 354, 783 10.1002/adsc.201101012
35. Wang, Y.; Liu, L.; Zhang, T.; Zhong, N.-J.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2012, 77, 4143 10.1021/jo3002535
36. Hu, F.-L.; Wei, Y.; Shi, M. Chem. Commun. 2014, 50, 8912 10.1039/C4CC03479A
37. Liu, Y.-L.; Wang, X.; Zhao, Y.-L.; Zhu, F.; Zeng, X.-P.; Chen, L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Angew. Chem., Int. Ed. 2013, 52, 13735 10.1002/anie.201307250
38. Wei, F.; Huang, H.-Y.; Zhong, N.-J.; Gu, C.-L.; Wang, D.; Liu, L. Org. Lett. 2015, 17, 1688 10.1021/acs.orglett.5b00456
39. Basavaiah, D.; Roy, S. Org. Lett. 2008, 10, 1819 10.1021/ol800424v
40. Zhang, L.; Liu, H.; Qiao, G.; Hou, Z.; Liu, Y.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2015, 137, 4316 10.1021/jacs.5b01138
41. Zheng, S.; Lu, X. Org. Lett. 2009, 11, 3978 10.1021/ol901618h
42. Steinhagen, H.; Corey, E. J. Angew. Chem., Int. Ed. 1999, 38, 1928 10.1002/(SICI)1521-3773(19990712)38:13/14<1928::AID-ANIE1928>3.0.CO;2-1
43. Avemaria, F.; Vanderheiden, S.; Bräse, S. Tetrahedron 2003, 59, 6785 10.1016/S0040-4020(03)00915-3
44. Yang, Q.-Q.; Xiao, C.; Lu, L.-Q.; An, J.; Tan, F.; Li, B.-J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 9137 10.1002/anie.201203657
45. Yang, Q.-Q.; Wang, Q.; An, J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Chem.-Eur. J. 2013, 19, 8401 10.1002/chem.201300988
46. Lee, A.; Younai, A.; Price, C. K.; Izquierdo, J.; Mishra, R. K.; Scheidt, K. A. J. Am. Chem. Soc. 2014, 136, 10589 10.1021/ja505880r
47. Hovey, M. T.; Check, C. T.; Sipher, A. F.; Scheidt, K. A. Angew. Chem., Int. Ed. 2014, 53, 9603 10.1002/anie.201405035
48. Peng, J.; Huang, X.; Jiang, L.; Cui, H.-L.; Chen, Y.-C. Org. Lett. 2011, 13, 4584 10.1021/ol201776h
49. Peng, J.; Huang, X.; Zheng, P.-F.; Chen, Y.-C. Org. Lett. 2013, 15, 5534 10.1021/ol402694b
50. Cui, H.-L.; Feng, X.; Peng, J.; Lei, J.; Jiang, K.; Chen, Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5737 10.1002/anie.200902093
51. Wang, Q.-G.; Zhou, Q.-Q.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2013, 15, 4786 10.1021/ol402158u
52. Peng, J.; Ran, G.-Y.; Du, W.; Chen, Y.-C. Synthesis 2015, 47, 2538 10.1055/s-0034-1378716
53. Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Curr. Opin. Drug Discovery Dev. 2010, 13, 758
54. Pellegrino, S.; Ruscica, M.; Magni, P.; Vistoli, G.; Gelmi, M. L. Bioorg. Med. Chem. 2013, 21, 5470 10.1016/j.bmc.2013.06.006
55. Mao, Z.; Baldwin, S. W. Org. Lett. 2004, 6, 2425 10.1021/ol0491888
56. Pellegrino, S.; Clerici, F.; Contini, A.; Leone, S.; Pilati, T.; Gelmi, M. L. Tetrahedron 2009, 65, 1995 10.1016/j.tet.2009.01.004
57. Zhang, Y.; Panek, J. S. Org. Lett. 2009, 11, 3366 10.1021/ol901202t
58. Gorokhovik, I.; Neuville, L.; Zhu, J. Org. Lett. 2011, 13, 5536 10.1021/ol202263a
59. Richmond, E.; Duguet, N.; Slawin, A. M. Z.; Lébl, T.; Smith, A. D. Org. Lett. 2012, 14, 2762 10.1021/ol300982f
60. Katayev, D.; Jia, Y.-X.; Sharma, A. K.; Banerjee, D.; Besnard, C.; Sunoj, R. B.; Kúndig, E. P. Chem.-Eur. J. 2013, 19, 11916 10.1002/chem.201301572
61. Zhou, F.; Cheng, G.-J.; Yang, W.; Long, Y.; Zhang, S.; Wu, Y.-D.; Zhang, X.; Cai, Q. Angew. Chem., Int. Ed. 2014, 53, 9555 10.1002/anie.201405575
62. Drouhin, P.; Hurst, T. E.; Whitwood, A. C.; Taylor, R. J. K. Org. Lett. 2014, 16, 4900 10.1021/ol5024129
63. El Bouakher, A.; Massip, S.; Jarry, C.; Troin, Y.; Abrunhosa-Thomas, I.; Guillaumet, G. Eur. J. Org. Chem. 2015, 2015, 556 10.1002/ejoc.201403292
64. Nibbs, A. E.; Montgomery, T. D.; Zhu, Y.; Rawal, V. H. J. Org. Chem. 2015, 80, 4928 10.1021/acs.joc.5b00277
65. For a review of using isatins as templates in synthesis of spirocyclic frameworks, see: Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104 10.1021/cr300135y
66. Viswambharan, B.; Selvakumar, K.; Madhavan, S.; Shanmugam, P. Org. Lett. 2010, 12, 2108 10.1021/ol100591r
67. Lingam, K. A. P.; Mandal, A. B.; Shanmugam, P. Tetrahedron Lett. 2011, 52, 3610 10.1016/j.tetlet.2011.05.009
68. Lingam, K; Shanmugam, P.; Selvakumar, K. Synlett 2012, 2012, 278 10.1055/s-0031-1290077
69. CCDC-1421940 (4a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data