Synthesis of 3-amino-3-hydroxymethyloxindoles and 3-hydroxy-3- hydroxymethyloxindoles by Rh2(OAc)4-catalyzed three-component reactions of 3-diazooxindoles with formaldehyde and anilines or water

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 3908-3916

  Wang, Chengjin ^a   Xing, Dong ^a   Wang, Dongwei ^a   Wu, Xiang ^a   Hu, Wenhao ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CATALYSIS; RHODIUM;

AMMONIUM YLIDES; CATALYZED DECOMPOSITIONS; OXONIUM; THREE COMPONENT REACTIONS; TITLE COMPOUNDS;

FORMALDEHYDE;

3 AMINO 3 HYDROXYMETHYLOXINDOLE DERIVATIVE; 3 DIAZOOXINDOLE DERIVATIVE; 3 HYDROXY 3 HYDROXYMETHYLOXINDOLE DERIVATIVE; AMMONIA; ANILINE; FORMALDEHYDE; INDOLE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG; WATER; 3-AMINO-3-HYDROXYMETHYLOXINDOLE; 3-HYDROXY-3-HYDROXYMETHYLOXINDOLE; ANILINE DERIVATIVE; ORGANOMETALLIC COMPOUND; RHODIUM TETRAACETATE;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; DECOMPOSITION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION OPTIMIZATION; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; FORMALDEHYDE; INDOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; WATER;

EID: 84899789320     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500307n     Document Type: Article

References (66)

1. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758
2. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381-1407
3. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20-38
4. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2963
5. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219
6. Trost, B. M.; Brennan, M. K. Synthesis 2009, 18, 3003-3025
7. Antonchick, A. P.; Gerding-Reimers, C.; Catarinella, M.; Schürmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735-740
8. Nicolaou, K. C.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Bella, M.; Snyder, S. A. J. Am. Chem. Soc. 2004, 126, 12888-12896
9. Netz, A.; Oost, T.; Geneste, H.; Braje, W. M.; Wernet, W.; Unger, L.; Hornberger, W.; Lubisch, W. PCT Int. Appl. WO2008080971.
10. Lin, X.-C.; Weinreb, S. M. Tetrahedron Lett. 2001, 42, 2631-2633
11. Silverio, D. L.; Torker, S.; Pilyugina, T.; Vieira, E. M.; Snapper, M. L.; Haeffner, F.; Hoveyda, A. H. Nature 2013, 494, 216-221
12. Bergonzini, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 971-974
13. Kitamura, H.; Kato, A.; Esaki, T. Eur. J. Pharmacol. 2001, 418, 225-230
14. Ochi, M.; Kawasaki, K.; Kataoka, H.; Uchio, Y. Biochem. Biophys. Res. Commun. 2001, 283, 1118-1123
15. Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159-3166
16. Erkizan, H. V.; Kong, Y.; Merchant, M.; Schlottmann, S.; Barber-Rotenberg, J. S.; Yuan, L.; Abaan, O. D.; Chou, T. H.; Dakshanamurthy, S.; Brown, M. L.; Uren, A.; Toretsky, J. A. Nat. Med. 2009, 15, 750-756
17. Kamano, Y.; Zhang, H.-P.; Ichhara, Y.; Kizu, H.; Komiyama, K.; Itokawa, H.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783-2784
18. Qiu, J.; Zhang, J.-X.; Liu, S.; Hao, X.-J. Tetrahedron Lett. 2013, 54, 300-302
19. Wang, C. H.; White, A. R.; Schwartz, S. N.; Alluri, S.; Cattabiani, T. M.; Zhang, L. K.; Buevich, A. V.; Ganguly, A. K.; Chan, T. M. Tetrahedron 2012, 68, 9750-9762
20. Guo, Q.-X.; Liu, Y.-W.; Li, X.-C.; Zhong, L.-Z.; Peng, Y.-G. J. Org. Chem. 2012, 77, 3589-3594
21. Alcaide, B.; Almendros, P.; Aragoncillo, C. Eur. J. Org. Chem. 2010, 2845-2848
22. Shi, Y. H.; Wang, Z.; Shi, Y.; Deng, W. P. Tetrahedron 2012, 68, 3649-3653
23. Zhou, F.; Ding, M.; Zhou, J. Org. Biomol. Chem. 2012, 10, 3178-3181
24. Emura, T.; Esaki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559-8564
25. Zhao, H.; Thurkauf, A.; Braun, J.; Brodbeck, R.; Kieltyka, A. Bioorg. Med. Chem. Lett. 2000, 10, 2119-2122
26. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255-1257
27. Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kundig, E. P. Chem. Commun. 2008, 4040-4042
28. Marsden, S. P.; Watson, E. L.; Raw, S. A. Org. Lett. 2008, 10, 2905-2908
29. Thakur, P. B.; Meshram, H. M. RSC Adv. 2014, 4, 5343-5350
30. Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem. 2006, 118, 3431-3434
31. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946-6948
32. Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Angew. Chem. 2010, 122, 756-759
33. Itoh, T.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2009, 11, 3854-3857
34. Liu, Y.-L.; Wang, B.-L.; Cao, J.-J.; Chen, L.; Zhang, Y.-X.; Wang, C.; Zhou, J. J. Am. Chem. Soc. 2010, 132, 15176-15178
35. Nakamura, T.; Shirokawa, S. I.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2006, 8, 677-679
36. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919-934
37. Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488-16489
38. Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2005, 70, 3198-3204
39. Alcaide, B.; Almendros, P.; Martínez del Campo, T.; Quirós, M. Chem.-Eur. J. 2009, 15, 3344-3346
40. Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515
41. Ueda, T.; Inada, M.; Okamoto, I.; Morita, N.; Tamura, O. Org. Lett. 2008, 10, 2043-2046
42. Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593-1595
43. Bui, T.; Candeias, N. R.; Barbas, C. F., III J. Am. Chem. Soc. 2010, 132, 5574-5575
44. Zhang, Z.; Zheng, W.; Antilla, C. J. Angew. Chem., Int. Ed. 2011, 50, 1135-1138
45. Yadav, J. S.; Subba Reddy, B. V.; Suresh Reddy, Ch.; Krishna, A. D. Tetrahedron Lett. 2007, 48, 2029-2032
46. Guo, X.; Hu, W.-H. Acc. Chem. Res. 2013, 46, 2427-2440
47. Xing, D.; Hu, W.-H. Tetrahedron Lett. 2014, 55, 777-783
48. Wang, Y.-H.; Chen, Z.-Y.; Mi, A.-Q.; Hu, W.-H. Chem. Commun. 2004, 2486-2487
49. Zhu, Y.-G.; Zhai, C.-W.; Yang, L.-P.; Hu, W.-H. Eur. J. Org. Chem. 2011, 1113-1124
50. Zhou, C.-Y.; Wang, J.-C.; Wei, J.; Xu, Z.-J.; Guo, Z.; Low, K.-H.; Che, C.-M. Angew. Chem., Int. Ed. 2012, 51, 11376-11380
51. Ren, L.; Lian, X.-L.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 3315-3318
52. Lu, C.-D.; Liu, H.; Chen, Z.-Y.; Hu, W.-H.; Mi, A.-Q. Org. Lett. 2005, 7, 83-86
53. Guo, X.; Huang, H.-X.; Yang, L.-P.; Hu, W.-H. Org. Lett. 2007, 9, 4721-4723
54. Zhang, X.; Huang, H.-X.; Guo, X.; Guan, X.-Y.; Yang, L.-P.; Hu, W.-H. Angew. Chem., Int. Ed. 2008, 47, 6647-6649
55. Wang, C.-J.; Liu, S.-Y.; Xing, D.; Wang, X.; Wu, X.; Hu, W.-H. Tetrahedron 2013, 69, 11203-11208
56. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Callejo, R.; Ruiz, M. P.; Torres, M. R. Eur. J. Org. Chem. 2012, 2359-2366
57. Ryang, H. S.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 2129-2131
58. Qu, Z.-H.; Shi, W.-F.; Wang, J.-B. J. Org. Chem. 2001, 66, 8139-8144
59. Muthusamy, S.; Gunanathan, C. Synlett 2003, 1599-1602
60. Marti, C.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505-11515
61. Reddy, B. V. S.; Rajasekaran, T.; Karthik, G.; Rao, T. P. Tetrahedron Lett. 2012, 53, 3416-3420
62. Cao, Z.-Y.; Zhou, F.; Yu, Y.-H.; Zhou, J. Org. Lett. 2012, 15, 42-45
63. Awata, A.; Arai, T. Synlett 2013, 29-32
64. Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. J. Am. Chem. Soc. 2013, 135, 8197-8200
65. Muthusamy, S.; Gunanathan, C.; Nethaji, M. J. Org. Chem. 2004, 69, 5631-5637
66. Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701-1705