Syntheses of CF2H-containing spirocyclopropyloxindoles from in situ generated CF2HCHN2 and 3-ylideneoxindoles

Tetrahedron

Volumn 73, Issue 39, 2017, Pages 5806-5812

  Han, Wen Yong ^a   Zhao, Jia ^a   Wang, Jian Shu ^a   Cui, Bao Dong ^a   Wan, Nan Wei ^a   Chen, Yong Zheng ^a  

^a ZUNYI MEDICAL UNIVERSITY   (China)

Author keywords

3 Ylideneoxindoles; Difluoromethyl diazomethane; Difluoromethyl group; Spirooxindoles; 3+2 cycloaddition ring contraction

Indexed keywords

3 YLIDENEOXINDOLE DERIVATIVE; CISPLATIN; CYTOTOXIC AGENT; ETHYL 1' BENZYL 3 (DIFLUOROMETHYL) 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 1' ETHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 1' METHYL 2' OXO 5' (TRIFLUOROMETHOXY)SPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 1',5' DIMETHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 2' OXO 1' PHENYLSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 5' FLUORO 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 7' FLUORO 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 3 (DIFLUOROMETHYL) 7' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 5' BROMO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 5' BROMO 3 (DIFLUOROMETHYL) 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 5' CHLORO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 6' BROMO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 6' CHLORO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 7' BROMO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; ETHYL 7' CHLORO 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; METHYL 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; OXINDOLE; PROPYL 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; SPIROCYCLOPROPYLOXINDOLE DERIVATIVE; TERT BUTYL 2 ETHYL 3 (DIFLUOROMETHYL) 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 1',2' DICARBOXYLATE; TERT BUTYL 3 (DIFLUOROMETHYL) 1' METHYL 2' OXOSPIRO[CYCLOPROPANE 1,3' INDOLINE] 2 CARBOXYLATE; UNCLASSIFIED DRUG;

A-549 CELL LINE; ARTICLE; CATALYST; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLOADDITION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; IC50; MALE; PRIORITY JOURNAL; PROSTATE CANCER CELL LINE;

EID: 85028332695     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2017.08.022     Document Type: Article

References (79)

1. For selected reviews on the oxindole unit as an attractive synthetic target in structurally complex and biologically active molecular, see:.
2. Dalpozzo, R., Bartoli, G., Bencivenni, G., Chem Soc Rev 41 (2012), 7247–7290.
3. Liu, Y., Han, S.-J., Liu, W.-B., Stoltz, B.M., Acc Chem Res 48 (2015), 740–751.
4. Yu, J.-S., Zhou, F., Liu, Y.-L., Zhou, J., Synlett 26 (2015), 2491–2504.
5. Mohammadi Ziarani, G., Moradi, R., Lashgari, N., Tetrahedron Asymm 26 (2015), 517–541.
6. Chen, J.-R., Yu, X.-Y., Xiao, W.-J., Synthesis 47 (2015), 604–629.
7. Kaur, M., Singh, M., Chadha, N., Silakari, O., Eur J Med Chem 123 (2016), 858–894.
8. For leading reviews on the spirooxindole core as a key structural feature in pharmaceuticals and natural products, see:.
9. Galliford, C.V., Scheidt, K.A., Angew Chem Int Ed 46 (2007), 8748–8758.
10. Santos, M.M.M., Tetrahedron 70 (2014), 9735–9757.
11. Yu, B., Yu, D.-Q., Liu, H.-M., Eur J Med Chem 97 (2015), 673–698.
12. Ye, N., Chen, H., Wold, E.A., Shi, P.-Y., Zhou, J., ACS Infect Dis 2 (2016), 382–392.
13. Yu, B., Zheng, Y.-C., Shi, X.-J., Qi, P.-P., Liu, H.-M., Anti-Cancer Agent Me 16 (2016), 1315–1324.
14. For recent selected reviews on the syntheses of spirooxindoles, see:.
15. Zhou, F., Liu, Y.-L., Zhou, J., Adv Synth Catal 352 (2010), 1381–1407.
16. Singh, G.S., Desta, Z.Y., Chem Rev 112 (2012), 6104–6155.
17. Ball-Jones, N.R., Badillo, J.J., Franz, A.K., Org Biomol Chem 10 (2012), 5165–5181.
18. Hong, L., Wang, R., Adv Synth Catal 355 (2013), 1023–1052.
19. Cheng, D., Ishihara, Y., Tan, B., Barbas, C.F. III, ACS Catal 4 (2014), 743–762.
20. Han, W.-Y., Zhao, J.-Q., Zuo, J., Xu, X.-Y., Zhang, X.-M., Yuan, W.-C., Adv Synth Catal 357 (2015), 3007–3031.
21. For recent selected examples on the syntheses of spirooxindoles bearing a five-membered ring, see:.
22. Namitharan, K., Zhu, T., Cheng, J., et al. Nat Commun, 5, 2014, 3982.
23. Zhao, J.-Q., Wu, Z.-J., Zhou, M.-Q., Xu, X.-Y., Zhang, X.-M., Yuan, W.-C., Org Lett 17 (2015), 5020–5023.
24. Zhao, J.-Q., Zhou, M.-Q., Wu, Z.-J., et al. Org Lett 17 (2015), 2238–2241.
25. Chen, L., Wu, Z.-J., Zhang, M.-L., et al. J Org Chem 80 (2015), 12668–12675.
26. Wang, H.-J., Pan, B.-W., Zhang, W.-H., et al. Tetrahedron, 71, 2015, 8131.
27. Wang, Z.-H., Wu, Z.-J., Yue, D.-F., et al. Chem Commun 52 (2016), 11708–11711.
28. Liu, X.-W., Yao, Z., Yang, J., et al. Tetrahedron 72 (2016), 1364–1374.
29. Yang, J., Liu, X.-W., Wang, D.-D., et al. Tetrahedron 72 (2016), 8523–8536.
30. Liu, R.-R., Xu, Y., Liang, R.-X., et al. Org Biomol Chem 15 (2017), 2711–2715.
31. Reddi, Y., Sunoj, R.B., ACS Catal 7 (2017), 530–537.
32. For recent selected examples on the syntheses of spirooxindoles bearing a six-membered ring, see:.
33. Ramachary, D.B., Venkaiah, C., Madhavachary, R., Org Lett 15 (2013), 3042–3045.
34. Chatterjee, I., Bastida, D., Melchiorre, P., Adv Synth Catal 355 (2013), 3124–3130.
35. Kim, K.H., Moon, H.R., Lee, J., Kim, J., Kim, J.N., Adv Synth Catal 357 (2015), 1532–1544.
36. Li, C., Lu, H., Sun, X.-X., Mei, G.-J., Shi, F., Org Biomol Chem 15 (2017), 4794–4797.
37. Zhou, Y., Lu, Y., Hu, X., et al. Chem Commun 53 (2017), 2060–2063.
38. Lin, W., Zhan, G., Shi, M., Du, W., Chen, Y., Chin J Chem 35 (2017), 857–860.
39. Jiang, T., Kuhen, K.L., Wolff, K., et al. Bioorg Med Chem Lett 16 (2006), 2105–2108.
40. Fensome, A; Mccomas, C. C; Melenski, E G; Marella, M A; Wrobel, J E; Grubb, G. S. U.S. Pat. Appl. Publ. US 20060030717 A1, 2006;.
41. Sampson, P. B.; Li, S.-W.; Liu, Y.; Pauls, H. W.; Edwards, L. G.; Forrest, B. T.; Feher, M.; Patel, N. K. B.; Pan, G. PCT Int. Appl. WO 2010115279 A1, 2010;.
42. Cockerill, S.; Pilkington, C.; Lumley, J.; Angell, R.; Mathews, N. PCT Int. Appl. WO 2013068769 A1, 2013;.
43. Yu, B., Yu, Z., Qi, P.-P., Yu, D.-Q., Liu, H.-M., Eur J Med Chem 95 (2015), 35–40.
44. Sampson, P.B., Liu, Y., Forrest, B., et al. J Med Chem 58 (2015), 147–169.
45. For a leading review, see:Cao, Z.-Y., Zhou, J., Org Chem Front 2 (2015), 849–858.
46. For selected examples, see:.
47. Dou, X., Lu, Y., Chem-Eur J 18 (2012), 8315–8319.
48. Noole, A., Ošeka, M., Pehk, T., et al. Adv Synth Catal 355 (2013), 829–835.
49. Li, T.-R., Duan, S.-W., Ding, W., et al. J Org Chem 79 (2014), 2296–2302.
50. Zhou, R., Yang, C., Liu, Y., Li, R., He, Z., J Org Chem 79 (2014), 10709–10715.
51. Reddy, C.N., Nayak, V.L., Mani, G.S., et al. Bioorg Med Chem Lett 25 (2015), 4580–4586.
52. Chi, Y., Qiu, L., Xu, X., Org Biomol Chem 14 (2016), 10357–10361.
53. Zhao, J.-Q., Yue, D.-F., Zhang, X.-M., Xu, X.-Y., Yuan, W.-C., Org Biomol Chem 14 (2016), 10946–10952.
54. Guo, J., Liu, Y., Li, X., Liu, X., Lin, L., Feng, X., Chem Sci 7 (2016), 2717–2721.
55. Chowdhury, M.A., Abdellatif, K.R.A., Dong, Y., Das, D., Suresh, M.R., Knaus, E.E., J Med Chem 52 (2009), 1525–1529.
56. Narjes, F., Koehler, K.F., Koch, U., et al. Bioorg Med Chem Lett 12 (2002), 701–704.
57. Xu, Y., Prestwich, G.D., J Org Chem 67 (2002), 7158–7161.
58. Kohl, B., Sturm, E., Senn-Bilfinger, J., et al. J Med Chem 35 (1992), 1049–1057.
59. Prous, J.R., Drugs Fut 20 (1995), 135–138.
60. Giornal, F., Pazenok, S., Rodefeld, L., Lui, N., Vors, J.-P., Leroux, F.R., J Fluor Chem 152 (2013), 2–11.
61. Selected examples for the preparation of difluoroalkylated compounds, see:.
62. Feng, Z., Min, Q.-Q., Xiao, Y.-L., Zhang, B., Zhang, X., Angew Chem, Int Ed 53 (2014), 1669–1673.
63. Xiao, Y.-L., Guo, W.-H., He, G.-Z., Pan, Q., Zhang, X., Angew Chem, Int Ed 53 (2014), 9909–9913.
64. Feng, Z., Min, Q.-Q., Zhang, X., Org Lett 18 (2016), 44–47.
65. Feng, Z., Min, Q.-Q., Fu, X.-P., An, L., Zhang, X., Nat Chem, 2017, 10.1038/nchem.2746.
66. Han, W.-Y., Zhao, J., Wang, J.-S., et al. Org Biomol Chem 15 (2017), 5571–5578.
67. Han, W.-Y., Li, S.-W., Wu, Z.-J., Zhang, X.-M., Yuan, W.-C., Chem Eur J 19 (2013), 5551–5556.
68. Shan, J., Cui, B., Wang, Y., et al. J Org Chem 81 (2016), 5270–5277.
69. For other examples on the construction of CF2H-containing molecules using in situ generated CF2HCHN2, see:.
70. Mykhailiuk, P.K., Angew Chem, Int Ed 54 (2015), 6558–6561.
71. Hock, K.J., Mertens, L., Koenigs, R.M., Chem Commun 52 (2016), 13783–13786.
72. Li, J., Yu, X.-L., Cossy, J., et al. Eur J Org Chem, 2017, 266–270.
73. CCDC 1532672 ((±)-(4a)), 1545278 ((±)-(4g)), 1545279 ((±)-(4r)) and 1557660 ((±)-4t) contain 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_request/cif.
74. For details, see the Supporting Information.
75. Jiang, T., Kuhen, K.L., Wolff, K., et al. Bioorg Med Chem Lett 16 (2006), 2109–2112.
76. Aratani, T., Nakanisi, Y., Nozaki, H., Tetrahedron 26 (1970), 4339–4346.
77. Adam, W., Bottle, S.E., Tetrahedron Lett 32 (1991), 1405–1408.
78. Palumbo, C., Mazzeo, G., Mazziotta, A., et al. Org Lett 13 (2011), 6248–6251.
79. Suman, K., Srinu, L., Thennarasu, S., Org Lett 16 (2014), 3732–3735.