Selective synthesis of functionalized spiro[indoline-3,2′-pyridines] and spiro[indoline-3,4′-pyridines] by lewis acid catalyzed reactions of acetylenedicarboxylate, arylamines, and isatins

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 4131-4136

  Gao, Hong ^a   Sun, Jing ^a   Yan, Chao Guo ^a  

^a YANGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DICHLOROMETHANE; SYNTHESIS (CHEMICAL);

ACETYLENEDICARBOXYLATE; ARYL AMINES; CATALYZED REACTIONS; FUNCTIONALIZED; LEWIS ACID-CATALYZED REACTIONS; SELECTIVE SYNTHESIS; THREE COMPONENT REACTIONS;

PYRIDINE;

ACETYLENEDICARBOXYLIC ACID; AROMATIC AMINE; DICARBOXYLIC ACID DERIVATIVE; DICHLOROMETHANE; FUNCTIONAL GROUP; ISATIN; ISATIN 3 IMINE; LEWIS ACID; PYRIDINE DERIVATIVE; SPIRO[INDOLINE 3,2' PYRIDINE] DERIVATIVE; SPIRO[INDOLINE 3,4' PYRIDINE] 2',3',5',6' TETRACARBOXYLIC ACID; SPIRO[INDOLINE 3,4' PYRIDINE] DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 84899788273     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500144z     Document Type: Article

References (51)

1. Zhu, J. P.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: New York, 2004.
2. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: New York, 2006.
3. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
4. Dömling, A. Chem. Rev. 2006, 106, 17-89
5. Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634
6. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210
7. Wessjohann, L. A.; Rivera, D. G.; Vercillo, O. E. Chem. Rev. 2009, 109, 796-814
8. Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083-3135
9. Singh, M. S.; Raghuvanshi, K. Tetrahedron 2012, 68, 8683-8697
10. Voskressensky, L. G.; Festa, A. A.; Varlamov, A. V. Tetrahedron 2014, 70, 551-572
11. Huisgen, R.; Morikawa, M.; Herbig, K.; Brunn, E. Chem. Ber. 1967, 100, 1094-1106
12. Huisgen, R. Z. Chem. 1968, 8, 290-298
13. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907
14. Nair, V.; Menon, R. S.; Sreekanth, A.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520-530
15. Kielland, N.; Lavilla, R. Top. Heterocycl. Chem. 2010, 25, 127-168
16. Shaabani, A.; Rezayan, A. H.; Sarvary, A. Mol. Divers. 2011, 15, 41-68
17. Nair, V.; Devipriya, S.; Suresh, E. Tetrahedron 2008, 64, 3567-3577
18. Nair, V.; Devipriya, S.; Suresh, E. Tetrahedron Lett. 2007, 48, 3667-3670
19. Nair, V.; Deepthi, A.; Manoj, P.; Bindu, S.; Sreekumar, V.; Beneesh, P. B.; Mohan, R.; Suresh, E. J. Org. Chem. 2006, 71, 2313-2319
20. Nair, V.; Sreekumar, V.; Bindu, S.; Suresh, E. Org. Lett. 2005, 7, 2297-2300
21. Yavari, I.; Mirzaei, A.; Moradi, L.; Khalili, G. Tetrahedron Lett. 2010, 51, 396-398
22. Yavari, I.; Seyfi, S.; Hossaini, Z. Tetrahedron Lett. 2010, 51, 2193-21949
23. Yavari, I.; Piltan, M.; Moradi, L. Tetrahedron 2009, 65, 2067-2071
24. Yavari, I.; Mokhtarporyani-Sanandaj, A.; Moradi, L.; Mirzaei, A. Tetrahedron 2008, 64, 5221-5225
25. Yadav, J. S.; Reddy, B. V. S.; Yadav, N. N.; Gupta, M. K.; Sridhar, B. J. Org. Chem. 2008, 73, 6857-6859
26. Ding, H. F.; Zhang, Y. P.; Bian, M.; Yao, W. J.; Ma, C. J. Org. Chem. 2008, 73, 578-584
27. Çavdar, H.; Saraçoglu, N. J. Org. Chem. 2006, 71, 7793-7799
28. Muthusamy, S.; Gunanathan, C.; Nethaji, M. J. Org. Chem. 2004, 69, 5631-5637
29. Sun, J.; Xia, E. Y.; Wu, Q.; Yan, C. G. Org. Lett. 2010, 12, 678
30. Sun, J.; Xia, E. Y.; Wu, Q.; Yan, C. G. ACS Comb. Sci. 2011, 13, 421-426
31. Sun, J.; Sun, Y.; Xia, E. Y.; Yan, C. G. ACS Comb. Sci. 2011, 13, 436-441
32. Gao, H.; Sun, J.; Yan, C. G. Tetrahedron 2013, 69, 589-594
33. Sun, J.; Sun, Y.; Gong, H.; Xie, Y. J.; Yan, C. G. Org. Lett. 2012, 14, 5172-5175
34. Han, Y.; Sun, Y.; Sun, J.; Yan, C. G. Tetrahedron 2012, 68, 8256-8260
35. Sun, J.; Sun, Y.; Gao, H.; Yan, C. Eur. J. Org. Chem. 2012, 1976-1983
36. Sun, J.; Zhu, D.; Gong, H.; Yan, C. G. Tetrahedron 2013, 69, 10565-10572
37. Gong, H.; Sun, J.; Yan, C. G. Synthesis 2014, 46, 489-495
38. Han, Y.; Wu, Q.; Sun, J.; Yan, C. Tetrahedron 2012, 68, 8539-8544
39. Sarkar, R.; Mukhopadhyay, C. Tetrahedron Lett. 2013, 54, 3706-3711
40. Kiruthika, S. E.; Amritha, R.; Perumal, P. T. Tetrahedron Lett. 2012, 53, 3268-3273
41. Sun, J.; Wu, Q.; Xia, E. Y.; Yan, C. G. Eur. J. Org. Chem. 2011, 2981-2986
42. Wang, X. S.; Zhou, J.; Yang, K.; Yao, C. S. Tetrahedron Lett. 2010, 51, 5721-5723
43. Maiti, G.; Karmakar, R.; Kayal, U. Tetrahedron Lett. 2013, 54, 2920-2923
44. Kouznetsov, V. V.; Forero, V. S. B.; Torres, D. F.A Tetrahedron Lett. 2008, 49, 5855-5857
45. Shi, F.; Xing, G. J.; Zhu, R. Y.; Tan, W.; Tu, S. J. Org. Lett. 2013, 15, 128-131
46. Gao, H.; Sun, J.; Yan, C. G. Synthesis 2014, 46, 489-495
47. Murphy, S. T.; Taylor, W. C.; Vadasz, A. Aust. J. Chem. 1982, 35, 1215-1225
48. Liu, W. B.; Jiang, H. F.; Huang, L. B. Org. Lett. 2010, 12, 312-315
49. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y. Z. Eur. J. Org. Chem. 2010, 4189-4193
50. Kikuchi, S.; Iwai, M.; Murayama, H.; Fukuzawa, S. Tetrahedron Lett. 2008, 49, 114-116
51. Sirijindalert, T.; Hansuthirakul, K.; Rashatasakhon, P.; Sukwattanasinitt, M.; Ajavakom, A. Tetrahedron 2010, 66, 5161-5167