Synthesis of oxindole-appended allyl amines and vinyl aziridines via InCl3/ArSH-mediated ring opening of vinyl aziridines and sulfur ylide aziridination

Synlett

Volumn 23, Issue 20, 2012, Pages 2903-2908

  Lingam, Kandapalam Arun Prasath ^a   Shanmugam, Ponnusamy ^a   Mandal, Asitbaran ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

cyclization; heterocycles; oxindole; ring opening; ylides

Indexed keywords

3 VINYLAZIRIDINE 2 OXINDOLE; ALLYLAMINE; AZIRIDINE DERIVATIVE; COERULESCINE; HORSFILINE; INDIUM CHLORIDE; ISATIN; N TOSYL IMINE; OXINDOLE; PYRROLIDINYLOXINDOLE; SPIROTRYPROSTATIN; STRYCHNOPHYLLINE; SULFUR YLIDE; TETRAHYDROTHIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL AZIRIDINE; VINYL AZIRIDINE 2 OXINDOLE;

ARTICLE; AZIRIDINATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ISOMERIZATION; PRECURSOR; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 84868683004     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317556     Document Type: Article

References (57)

1. Tanner D. Angew. Chem., Int. Ed. Engl.: 1994; 33 599
2. Tanner D. Pure. Appl. Chem.: 1993; 65 1319
3. Osborn H. M. I, Sweeney J. Tetrahedron: Asymmetry: 1997; 8 1693
4. Muller P., Fruit C. Chem. Rev.: 2003; 103 2905
5. Aggarwal V. K., Alonso E., Fang G. Y., Ferrara M., Hynd G., Porcelloni M. Angew. Chem. Int. Ed.: 2001; 40 1433
6. Aggarwal V. K., Ferrara M., OBrian C. J., Thompson A., Jones R. V. H, Fieldhouse R. J. Chem. Soc., Perkin Trans. 1: 2001; 1635
7. Aggarwal V. K., Alonso E., Ferrara M., Spey S. E. J. Org. Chem.: 2002; 67 2335
8. Li A.-H, Dai L.-X, Hou X.-L, Chen M.-B. J. Org. Chem.: 1996; 61 4641
9. Hou X.-L, Yang X.-F, Dai L.-X, Chen X.-F. Chem. Commun.: 1998; 747
10. Yang X.-F, Zhang M.-J, Hou X.-L, Dai L. X. J. Org. Chem.: 2002; 67 8097
11. Motamed M., Bunnelle E. M., Singaram S. W., Sarpong R. Org. Lett.: 2007; 9 2167
12. Lowe M. A., Ostovar M., Ferrini S., Chen C.-C, Lawrence P. G., Fontana F., Calabrese A. A., Aggarwal V. K. Angew. Chem. Int. Ed.: 2011; 50 6370
13. Ahman J., Jarevang T., Somfai P. J. Org. Chem.: 1996; 61 8148
14. Lindstrom U. L., Somfai P. Chem.-Eur. J.: 2001; 7 94
15. Rubin M., Rubina M., Gevorgyan V. Chem. Rev.: 2007; 107 3117
16. Lebel H., Marcoux J.-F, Molinaro C., Charette A. B. Chem. Rev.: 2003; 103 977
17. Jiang H., Deng X., Sun X., Tang Y., Dai L.-X. J. Org. Chem.: 2005; 70 10202
18. Ye S., Huang Z. Z., Xia C. A., Tang Y., Dai L.-X. J. Am. Chem. Soc.: 2002; 124 2432
19. Carson C. A., Kerr M. A. Chem. Soc. Rev.: 2009; 38 3051
20. Oba M., Nishiyama N., Nishiyama K. Tetrahedron: 2005; 61 8456
21. Brichacek M., Lee D., Njardarson J. T. Org. Lett.: 2008; 10 5023
22. Pellissier H. Tetrahedron: 2008; 64 7041
23. Zhu B.-H, Zheng J.-C, Yu C.-B, Sun X.-L, Zhou Y.-G, Shen Q., Tang Y. Org. Lett.: 2010; 12 504
24. Yang X. F., Zhang M. J., Hou X.-L, Dai L.-X. J. Org. Chem.: 2002; 67 8097
25. Aggarwal V. K., Winn C. L. Acc. Chem. Res.: 2004; 37 611
26. Janardanan D., Sunoj R. B. J. Org. Chem.: 2008; 73 8163
27. Dokli I., Matanovic I., Hamers Z. Chem. Eur. J.: 2010; 16 11744
28. Rajeev R., Sunoj R. B. Org. Biomol. Chem.: 2011; 9 2123
29. Saito T., Sakairi M., Akiba D. Tetrahedron Lett.: 2001; 42 5451
30. Morton D., Pearson D., Field R. A., Stockman R. A. Synlett: 2003; 1985
31. Solladie-Cavallo A., Roje M., Welter R., Sunjiae V. J. Org. Chem.: 2004; 69 1409
32. Morton D., Pearson D., Field R. A., Stockman R. A. Org. Lett.: 2005; 6 2377
33. Singh A., Roth G. P. Org. Lett.: 2011; 13 2118
34. Liu T.-L, Xue Z.-Y, Tao H.-Y, Wang C.-J. Org. Biomol. Chem.: 2011; 9 1980
35. Cheng M. N., Wang H., Gong L. Z. Org. Lett.: 2011; 13 2418
36. Zhong F., Chen G. Y., Lu Y. Org. Lett.: 2011; 13 82
37. Deng H.-P, Wei Y., Shi M. Org. Lett.: 2011; 13 3348
38. Tan B., Candeias N. R., Barbas C. F. III. J. Am. Chem. Soc.: 2011; 133 4672
39. Selvakumar K., Vaithiyanathan V., Shanmugam P. Chem. Commun.: 2010; 46 2826
40. Lingam K. A. P, Mandal A. B., Shanmugam P. Tetrahedron Lett.: 2011; 52 3610
41. Lingam K. A. P, Shanmugam P., Selvakumar K. Synlett: 2012; 23 278
42. Molinski T. F., Ireland C. M. J. Org. Chem.: 1988; 53 2103
43. Iwami M., Kiyoto S., Terano H., Kohsaka M., Aoki H., Imanaka H. J. Antibiot.: 1987; 40 589
44. Kumar U. K. S, Ila H., Junjappa H. Org. Lett.: 2001; 3 4193
45. Trost B. M., Fandrick D. R. Org. Lett.: 2005; 7 823
46. Trost B. M., Crawley M. L. Chem. Rev.: 2003; 103 2921
47. Johannsen M., Jorgensen K. A. Chem. Rev.: 1998; 98 1689
48. Trost B. M. Angew. Chem., Int. Ed. Engl.: 1989; 101 1173
49. Magnus P., Lacour J., Coldham I., Murgrage B., Banta W. B. Tetrahedron: 1995; 51 11087
50. Burgess K., Liu L. T., Pal B. J. Org. Chem.: 1993; 58 4758
51. Hayashi T., Yamamoto A., Ito Y., Nishioka E., Miura H., Yanagi K. J. Am. Chem. Soc.: 1989; 111 6301
52. Nair V., Ros S., Jayan C. N., Pillai B. S. Tetrahedron: 2004; 60 1959
53. Yadav J. S., Reddy B. V. S, Abraham S., Sabitha G. Tetrahedron Lett.: 2002; 43 1565
54. Singh M. S., Raghuvanshi K. Tetrahedron: 2012; 68 8683
55. Acharya C., Dey S., Jaisankar P. Tetrahedron Lett.: 2012; 53 5548
56. Bach R. D., Dmitrenko O., Thorpe C. J. Org. Chem.: 2008; 73 12
57. Kuramochi K., Sunoki T., Tsubaki K., Mizushina Y., Sakaguchi K., Sugawara F., Ikekita M., Kobayashi S. Bioorg. Med. Chem.: 2011; 19 4162