A novel MgI2 mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adduct of isatin: A facile synthesis of 3-spirocyclopropane-2-oxindole derivatives

Tetrahedron Letters

Volumn 52, Issue 28, 2011, Pages 3610-3613

  Lingam, Kandapalam Arun Prasath ^a   Mandal, Asit Baran ^a   Shanmugam, Ponnusamy ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Dimerization spirocyclopropanation; Isatin; Magnesium iodide; Morita Baylis Hillman adduct; Spirocyclopropane 2 oxindole

Indexed keywords

3 SPIROCYCLOPROPANE 2 OXINDOLE DERIVATIVE; ISATIN; MAGNESIUM DERIVATIVE; MAGNESIUM IODIDE; OXINDOLE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOPROPANATION; DIMERIZATION; INFRARED SPECTROSCOPY; ISOMERIZATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 80955180590     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.009     Document Type: Article

References (50)

1. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
2. H. Lebel, J. Marcoux, C. Molinaro, and A.B. Charette Chem. Rev. 103 2003 977 1050
3. C.A. Carson, and M.A. Kerr Chem. Soc. Rev. 38 2009 3051 3060
4. M. Rubin, M. Rubina, and V. Gevorgyan Chem. Rev. 107 2007 3117 3179
5. D. Agrawal, and V.K. Yadav Chem. Commun. 2008 6471 6488
6. P.D. Pohlhaus, S.D. Sanders, A.T. Parsons, W. Li, and J.S. Johnson J. Am. Chem. Soc. 130 2008 8642 8650
7. L.A. Adams, V.K. Aggarwal, R.V. Bonnert, B. Bressel, R.J. Cox, J. Shepherd, J.D. Vicente, M. Walter, W.G. Whittingham, and C.L. Winn J. Org. Chem. 68 2003 9433 9440
8. V.S. Korotkov, O.V. Larionov, A. Hofmeister, J. Magull, and A.D. Meijere J. Org. Chem. 72 2007 7504 7510
9. G.B. Bennett, R.B. Mason, and M.J. Shapiro J. Org. Chem. 43 1978 4383 4385
10. M. Chiericato, P.D. Croce, and E. Licandro J. Chem. Soc., Perkin Trans. 1 1979 211 213
11. M.K. Eberle, G.G. Kahle, and M.J. Shapiro J. Org. Chem. 47 1982 2210 2212
12. H. Yu, Y. Liu, H. Zhang, J. Chen, H. Deng, M. Shao, Z. Ren, and W. Cao Tetrahedron 66 2010 2598 2601
13. S. Muthusamy, E. Azhagan, B. Ganaprakasam, and E. Suresh Tetrahedron Lett. 51 2010 5662 5665
14. P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, and E.M. Carreira Angew. Chem., Int. Ed. 38 1999 3186 3189
15. C.-B. Cui, H. Kakeya, and H. Osada Tetrahedron 52 1996 12651 12666
16. K.C. Chan, F. Morsingh, and G.B. Yeoh J. Chem. Soc. C: Org. 1966 2245 2249
17. P.R. Sebahar, and R.M. Williams J. Am. Chem. Soc. 122 2000 5666 5667
18. R. Faust Angew. Chem., Int. Ed. 40 2001 2251 2253
19. D.W. Robertson, J.H. Krushinski, G.D. Pollock, H. Wilson, R.F. Kauffman, and J.S. Hayes J. Med. Chem. 30 1987 824 829
20. Cordon, M. E.; Karp, G. M.; Birk, J. H. European Patent 459, 133, 1991; Chem. Abstr. 1992, 117, 48332.
21. Condon, M. E.; Karp, G. M. European Patent 549, 892, 1993; Chem. Abstr. 1993, 119, 225817.
22. T. Jiang, K.L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T.Y. Wub, and Y. Hea Bioorg. Med. Chem. 16 2006 2105 2108
23. S.K. Jackson, A. Karadeolian, A.B. Driega, and M.A. Kerr J. Am. Chem. Soc. 130 2008 4196 4201
24. C.A. Carson, and M.A. Kerr J. Org. Chem. 70 2005 8242 8244
25. I.S. Young, and M.A. Kerr Angew. Chem., Int. Ed. 42 2003 3023 3026
26. P.D. Pohlhaus, and J.S. Johnson J. Am. Chem. Soc. 127 2005 16014 16015
27. S. Sebelius, V.J. Olsson, and K.J. Szabo J. Am. Chem. Soc. 127 2005 10478 10479
28. A. Lerchner, and M.E. Carreira J. Am. Chem. Soc. 124 2002 14826 14827
29. A. Kattuboina, P. Kaur, C. Timmons, and G. Li Org. Lett. 8 2006 2771 2774
30. C. Timmons, A. Kattuboina, S. Banerjee, and G. Li Tetrahedron 62 2006 7151 7154
31. M.E. Scott, C.A. Schwarz, and M. Lautens Org. Lett. 8 2006 5521 5524
32. C. Meyers, and E.M. Carreira Angew. Chem., Int. Ed. 42 2003 694 696
33. O. Sugimoto, K. Aoki, and K-i. Tanji Tetrahedron Lett. 45 2004 1915 1917
34. C.-J. Li, and W.-C. Zhang J. Am. Chem. Soc. 120 1998 9102 9103
35. I. Mutule, and E. Suna Tetrahedron 61 2005 11168 11176
36. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
37. S. Batra, and V. Singh Tetrahedron 64 2008 4511 4574
38. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48
39. E. Ciganek Organic Reactions L. Paquette, 1997 Wiley New York Vol. 51, p 201
40. G.-N. Ma, J.-J. Jiang, M. Shi, and Y. Wei Chem. Commun. 2009 5496 5514
41. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
42. K. Selvakumar, V. Vaithiyanathan, and P. Shanmugam Chem. Commun. 46 2010 2826 2828
43. B. Viswambharan, K. Selvakumar, M. Suchithra, and P. Shanmugam Org. Lett. 12 2010 2108 2111
44. P. Shanmugam, B. Viswambharan, and M. Suchithra Org. Lett. 9 2007 4095 4098
45. P. Shanmugam, V. Vaithiyanathan, and V. Baby Tetrahedron 62 2006 4342 4347
46. S.J. Garden, and J.M.S. Skakleb Tetrahedron Lett. 43 2002 1969 1972
47. P. Shanmugam, and B. Viswambharan Synlett 2008 2763 2768
48. Crystallographic data for 5a have been deposited (CCDC 806108) with the Cambridge Crystallographic Data Centre. Copy of the data can be obtained free of charge on application to 12, Union Road, Cambridge CB21EZ, UK (fax: +441223 336 033; e-mail: deposit@ccdc.cam.ac.uk )
49. W.-C. Zhang, and C.-J. Li J. Org. Chem. 64 1999 3230 3236
50. D.A. Lanfranchi, C. Bour, B. Boff, and G. Hanquet Eur. J. Org. Chem. 1 2010 5232 5247