Stereoselective synthesis of pyrrolo[1,2-a]indoles from allenes in PEG-400 as the reaction medium

Synlett

Volumn , Issue 9, 2011, Pages 1288-1292

  Phani Pavan, M ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

3 chloro 2 formylindole; allenes; domino cyclization; PEG 400; pyrroloindoles

Indexed keywords

3 CHLORO 2 FORMYLINDOLE; ALLENE DERIVATIVE; ALLENYLPHOSPHONATE DERIVATIVE; ALPHA ARYL ALLENYLPHOSPHONATE DERIVATIVE; ALPHA METHYL ALLENYLPHOSPHONATE DERIVATIVE; MACROGOL 400; PHOSPHONO PYRROLOINDOLE; POTASSIUM CARBONATE; PYRROLO[1,2 ALPHA]INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 79957489915     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260533     Document Type: Article

References (64)

1. Orlemans E O. M., Verboom W, Scheltinga M W., Reinhoudt D N., Lelieveld P, Fiebig H H., Winterhalter B R., Double J A., Bibby M C., J. Med. Chem. 1989 32 1612
2. Galm U, Hanger M H., Lanen S G. V., Ju J, Thorson J S., Shen B, Chem. Rev. 2005 105 739
3. Paris D, Cottin M, Demonchaux P, Augert G, Dupassieux P, Lenoir P, Peck M J., Jasserand D, J. Med. Chem. 1995 38 669
4. Wilson R M., Thaji R K., Bergman R G., Ellman J A., Org. Lett. 2006 8 1745
5. Fernandez L S., Buchanan M S., Carroll A R., Feng Y J., Quinn R J., Avery V M., Org. Lett. 2009 11 329
6. Molander G A., Schmitt M H., J. Org. Chem. 2000 65 3767
7. Tanaka M, Ubukata M, Matsuo T, Yasue K, Matsumoto K, Kajimoto Y, Ogo T, Inaba T, Org. Lett. 2007 9 3331
8. Flitsch W, Lubisch W, Chem. Ber. 1984 117 1424
9. Padwa A, Fryxell G E., Gasdaska J R., Venakatraman M K., Wong G S., J. Org. Chem. 1989 54 644
10. Coleman R S., Chen W, Org. Lett. 2001 3 1141
11. Miki Y, Hachiken H, Kawazoe A, Tsuzaki Y, Yanase N, Heterocycles 2001 55 1291
12. Yavari I, Adib M, Sayahi M H., J. Chem. Soc., Perkin Trans. 1 2002 1517
13. Borah H N., Deb M L., Boruah R C., Bhuvan P J., Tetrahedron lett. 2005 46 3391
14. Abbiati G, Casoni A, Canevari V, Nava D, Rossi E, Org. Lett. 2006 8 4839
15. Manian R D. R. S., Jayashankaran J, Raghunanthan R, Synlett 2007 874
16. Hong L, Sun W, Liu C, Wang L, Wang R, Chem. Eur. J. 2010 16 440
17. For selected recent reviews, see:, Yamamoto Y, Radhakrishnan U, Chem. Soc. Rev. 1999 28 199
18. Lu X, Zhang C, Xu Z, Acc. Chem. Res. 2001 34 535
19. Bates R W., Satcharoen V, Chem. Soc. Rev. 2002 31 12
20. Wei L.-L, Xiong H, Hsung R P., Acc. Chem. Res. 2003 36 773
21. Ma S, Acc. Chem. Res. 2003 36 701
22. Hoffmann-Röder A, Krause N, Angew. Chem. Int. Ed. 2004 43 1196
23. Modern Allene Chemistry Krause N Hashmi A S. K. Wiley-VCH Weinheim 2004
24. Brandsma L, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques Elsevier Oxford 2004
25. Ma S, Chem. Rev. 2005 105 2829
26. Nair V, Menon R S., Sreekanth A R., Abhilash N, Biju A T., Acc. Chem. Res. 2006 39 520
27. Ma S, Aldrichimica Acta 2007 40 91
28. Pacheco M C., Purser S, Gouverneur V, Chem. Rev. 2008 108 1943
29. Brasholz M, Reissig H.-U, Zimmer R, Acc. Chem. Res. 2009 42 45
30. Ma S, Acc. Chem. Res. 2009 42 1679
31. Deagostino A, Prandi C, Tabasso S, Venturello P, Molecules 2010 15 2667
32. Chakravarty M, Kumara Swamy K C., J. Org. Chem. 2006 71 9128
33. Kumara Swamy K C., Balaraman E, Satish Kumar N, Tetrahedron 2006 62 10152
34. Chakravarty M, Kumara Swamy K C., Synthesis 2007 3171
35. Yu F, Lian X, Ma S, Org. Lett. 2007 9 1703
36. Bravo-Altamirano K, Abrunhosa-Thomas I, Montchamp J.-L, J. Org. Chem. 2008 73 2292
37. Panossian A, Fleury-Bregeot N, Marinetti A, Eur. J. Org. Chem. 2008 3826
38. Chakravarty M, Bhuvan Kumar N N., Sajna K V., Kumara Swamy K C., Eur. J. Org. Chem. 2008 4500
39. Brady P B., Morris E M., Fenton O S., Sculimbrene B R., Tetrahedron Lett. 2009 50 975
40. Hirata Y, Inui T, Nakao Y, Hiyama T, J. Am. Chem. Soc. 2009 131 6624
41. Li W, Shi M, Eur. J. Org. Chem. 2009 270
42. Zhou C, Fang Z, Fu C, Ma S, J. Org. Chem. 2009 74 2887
43. Phani Pavan M, Chakravarty M, Kumara Swamy K C., Eur. J. Org. Chem. 2009 5927
44. Sajna K V., Kotikalapudi R, Chakravarty M, Bhuvan Kumar N N., Kumara Swamy K C., J. Org. Chem. 2011 76 920
45. For reactions of allenic esters and ketones with salicyl N -tosylimines or aldehydes, see:, Shi Y.-L, Shi M, Org. Lett. 2005 7 3057
46. Zhao G.-L, Shi Y.-L, Shi M, Org. Lett. 2005 7 4527
47. Shi M, Dai L.-Z, Shi Y.-L, Zhao G.-L, Adv. Synth. Catal. 2006 348 967
48. Dai L.-Z, Shi Y.-L, Zhao G.-L, Shi M, Chem. Eur. J. 2007 13 3701
49. Meng X, Huang Y, Chen R, Org. Lett. 2009 11 137
50. Meng X, Huang Y, Zhao H, Xie P, Ma J, Chen R, Org. Lett. 2009 11 991
51. Sun Y.-W, Guan X.-Y, Shi M, Org. Lett. 2010 12 5664
52. 3 as the base, although yields were very good, see:, Bhuvan Kumar N N., Nagarjuna Reddy M, Kumara Swamy K C., J. Org. Chem. 2009 74 5395
53. Majo V J., Perumal P T., J. Org. Chem. 1996 61 6523
54. Guillemin J C., Savignac P, Denis J M., Inorg. Chem. 1991 30 2170
55. Iorga B, Eymery F, Carmichael D, Savignac P, Eur. J. Org. Chem. 2000 3103
56. Bhuvan Kumar N N., Chakravarty M, Satish Kumar N, Sajna K V., Kumara Swamy K C., J. Chem. Sci. 2009 121 23
57. 9, See also:, Phani Pavan M, Dissertation University of Hyderabad India 2010
58. Lang R W., Hansen H.-J, Org. Synth., Coll. Vol. VII John Wiley & Sons London 1990 232
59. Ma S, Jiao N, Zhao S, Hou H, J. Org. Chem. 2002 67 2837
60. Scheufler F, Maier M E., Eur. J. Org. Chem. 2000 3945
61. X-ray data for compounds 11 (CCDC 806280) and 12 (CCDC 806281) were collected on OXFORD diffractometer using Mo-K ( = 0.71073 Å) radiation. The structures were solved and refined by standard methods, see:, Sheldrick G M., SADABS, Siemens Area Detector Absorption Correction University of Göttingen Germany 1996
62. Sheldrick G M., SHELX - 97: A program for crystal structure solution and refinement University of Göttingen Germany 1997
63. Sheldrick G M., SHELXTL NT Crystal Structure Analysis Package Version 5 Bruker AXS Analytical X-ray System WI (USA) 1999
64. The requirement for a good electron-withdrawing substituent to increase the reactivity of the indole has been reported, see:, Pintori D G., Greaney M F., J. Am. Chem. Soc. 2011 133 1209