Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols

Tetrahedron

Volumn 64, Issue 29, 2008, Pages 6876-6883

  Seregin, Ilya V ^a   Schammel, Alex W ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GERMYL; GOLD; HYDROGEN; INDOLIZINE DERIVATIVE; METAL DERIVATIVE; SILVER; SILYL; STANNYL;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ISOMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; PURIFICATION; SYNTHESIS;

EID: 44949130561     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.023     Document Type: Article

References (89)

1. For review, see:. Michael J.P. Nat. Prod. Rep. 16 (1999) 675
2. For pharmacologically important indolizines, see:
3. Schoeffter P., and Hoyer D. Naunyn Schmiedebergs Arch. Pharmacol. 339 (1989) 675
4. Fujita T., Matsumoto Y., Kimura T., Yokota S., Sawada M., Majima M., Ohtani Y., and Kumagai Y. Br. J. Clin. Pharmacol. 54 (2002) 283
5. Nakayama O., Hirosumi J., Chida N., Takahashi S., Sawada K., Kojo H., and Notsu Y. Prostate 31 (1997) 241
6. Facompre M., Tardy C., Bal-Mahieu C., Colson P., Perez C., Manzanares I., Cuevas C., and Bailly C. Cancer Res. 63 (2003) 7392
7. For studies on biological activity of Lamellarin family, see:
8. See Ref. 3.
9. Reddy M.V., Rao M.R., Rhodes D., Hansen M.S., Rubins K., Bushman F.D., Venkateswarlu Y., and Faulkner D.J. J. Med. Chem. 42 (1999) 1901
10. Østby O.B., Dalhus B., Gundersen L.-L., Rise F., Bast A., and Haenen G.R.M.M. Eur. J. Org. Chem. (2000) 3763
11. See Ref. 4b.
12. Gundersen L.-L., Malterud K.E., Negussie A.H., Rise F., Teklu S., and Østby O.B. Bioorg. Med. Chem. 11 (2003) 5409
13. Teklu S., Gundersen L.-L., Larsen T., Malterud K.E., and Rise F. Bioorg. Med. Chem. 13 (2005) 3127
14. 2 inhibition activity, see:. Hagishita S., Yamada M., Shirahase K., Okada T., Murakami Y., Ito Y., Matsuura T., Wada M., Kato T., Ueno M., Chikazawa Y., Yamada K., Ono T., Teshirogi I., and Ohtani M. J. Med. Chem. 39 (1996) 3636
15. Gautier, P.; Marchionni, D.; Roccon, A.; Tonnerre, B.; Wagnon, J. FR 2893616, 2007.
16. See Ref. 7.
17. For the most comprehensive review, see:
18. Behnisch A., Behnisch P., Eggenweiler M., and Wallenhorst T. Indolizine. Houben-Weyl Vol. E6a/2a (1994), Thieme, Stuttgart, Germany pp 323-450
19. See also:
20. Marchalin S., Baumlova B., Baran P., Oulyadi H., and Daich A. J. Org. Chem. 71 (2006) 9114
21. Kaloko Jr. J., and Hayford A. Org. Lett. 7 (2005) 4305
22. Kel'in A.V., Sromek A.W., and Gevorgyan V. J. Am. Chem. Soc. 123 (2001) 2074
23. Kel'in A.V., and Gevorgyan V. J. Org. Chem. 67 (2002) 95
24. Sromek A.W., Kel'in A.V., and Gevorgyan V. Angew. Chem., Int. Ed. 43 (2004) 2280
25. Schwier T., Sromek A.W., Yap D.M.L., Chernyak D., and Gevorgyan V. J. Am. Chem. Soc. 129 (2007) 9868
26. For other syntheses of heterocycles proceeding via 1,2-migrations, see:
27. Kim J.T., Kel'in A.V., and Gevorgyan V. Angew. Chem., Int. Ed. 42 (2003) 98
28. Dudnik A.S., and Gevorgyan V. Angew. Chem., Int. Ed. 46 (2007) 5195
29. Dudnik A.S., Sromek A.W., Rubina M., Kim J.T., Kel'in A.V., and Gevorgyan V. J. Am. Chem. Soc. 130 (2008) 1440
30. Seregin I.V., Schammel A.W., and Gevorgyan V. Org. Lett. 9 (2007) 3433
31. When this project was underway, a report on a related Pt-catalyzed 1,2-migration/cyclization toward indolizine core appeared, see:. Smith C.R., Bunnelle E.M., Rhodes A.J., and Sarpong R. Org. Lett. 9 (2007) 1169
32. Seregin I.V., and Gevorgyan V. J. Am. Chem. Soc. 128 (2006) 12050
33. For recent discussions on the role of Brønsted acids in transtion metal-catalyzed transformations, see:
34. Hashmi A.S.K. Catal. Today 122 (2007) 211
35. Li Z., Zhang J., Brouwer C., Yang C.-G., Reich N.W., and He C. Org. Lett. 8 (2006) 4175
36. Rosenfeld D.C., Shekhar S., Takemiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179
37. Rhee J.U., and Krische M.J. Org. Lett. 7 (2005) 2493
38. For acid-promoted isomerization of propargylic alcohols into α,β-unsaturated systems, see:. Erenler R., and Biellmann J.-F. Tetrahedron Lett. 46 (2005) 5683
39. Seregin I.V., Ryabova V., and Gevorgyan V. J. Am. Chem. Soc. 129 (2007) 7742
40. For selected examples on nucleophilic attack of heteroatom at alkyne activated by Au and Ag complexes, see:
41. Gorin D.J., Davis N.R., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 11260
42. Dubé P., and Toste F.D. J. Am. Chem. Soc. 128 (2006) 12062
43. Shapiro N.D., and Toste N.D. J. Am. Chem. Soc. 129 (2007) 4160
44. Hashmi A.S.K., Rudolph M., Schymura S., Visus J., and Frey W. Eur. J. Org. Chem. (2006) 4905
45. Hashmi A.S.K., Weyrauch J.P., Frey W., and Bats J.W. Org. Lett. 6 (2004) 4391
46. Belting V., and Krause N. Org. Lett. 8 (2006) 4489
47. Sun J., and Kozmin S.A. Angew. Chem., Int. Ed. 45 (2006) 4991
48. Wang S., and Zhang L. J. Am. Chem. Soc. 128 (2006) 14274
49. McDonald F.E., and Gleason M.M. J. Am. Chem. Soc. 118 (1996) 6648
50. McDonald F.E., Burova S.A., and Huffman L.G. Synthesis (2000) 970
51. For an example of a base-assisted substantial deuterium scrambling upon cycloisomerization in conjugated propargylic systems, see Ref. 11a.
52. For an example of clean 1,2-deuterium shift upon cycloisomerization, see:. Sromek A.W., Rubina M., and Gevorgyan V. J. Am. Chem. Soc. 127 (2005) 10500
53. Deuterium-labeled propargylic substrate 7 was prepared via the following sequence of steps.{A figure is presented}
54. For reviews, see:
55. Wakatsuki Y. J. Organomet. Chem. 689 (2004) 4092
56. Bruneau C., and Dixneuf P.H. Acc. Chem. Res. 32 (1999) 311
57. See also:
58. McDonald F.E. Chem.-Eur. J. 5 (1999) 3103
59. For a recent example, see:. Grotjahn D.B., Zeng X., and Cooksy A.L. J. Am. Chem. Soc. 128 (2006) 2798
60. See, for example:
61. See Ref. 19i.
62. See Ref. 19j.
63. Miura T., and Iwasawa N. J. Am. Chem. Soc. 124 (2002) 518
64. Mamane V., Hannen P., and Fürstner A. Chem.-Eur. J. 10 (2004) 4556
65. Katayama H., Wada C., Taniguchi K., and Ozawa F. Organometallics 21 (2002) 3285
66. Shirakawa E., Morita R., Tsuchimoto T., and Kawakami Y. J. Am. Chem. Soc. 126 (2004) 13614
67. For recent reviews on Au-catalyzed reactions, see:
68. Hoffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387
69. Hashmi A.S.K. Gold Bull. 37 (2004) 51
70. For Au-catalyzed synthesis of heterocycles, see:
71. Hashmi A.S.K., Schwarz L., Choi J.-H., and Frost T.M. Angew. Chem., Int. Ed. 39 (2000) 2285
72. Yao T., Zhang X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 11164
73. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 127 (2005) 6962
74. Hoffmann-Röder A., and Krause N. Org. Lett. 3 (2001) 2537
75. See Ref. 21.
76. For Au-catalyzed carbocyclizations, see for example:
77. Fürstner A., and Hannen P. Chem. Commun. (2004) 2546
78. Shi X., Gorin D.J., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 5802
79. Luzung M.R., Markham J.P., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 10858
80. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 11806
81. Nieto-Oberhuber C., Lopez S., and Echavarren A.M. J. Am. Chem. Soc. 127 (2005) 6178
82. See also:
83. Asao N., Takahashi K., Lee S., Kasahara T., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 12650
84. Shi Z., and He C. J. Am. Chem. Soc. 126 (2004) 5964
85. Zhang L. J. Am. Chem. Soc. 127 (2005) 16804
86. 3 as a precatalyst, the latter can be reduced into Au(I) species via various redox processes. See, Ref. 30b.
87. For discussion on Au-catalyzed propargyl-allenyl prototropic isomerization, see Ref. 10c.
88. Control experiment indicated no proton-deuterium scrambling in the cyclized product.{A figure is presented}
89. For Au-catalyzed migration of alkyl group in indole series, see:. Alfonsi M., Arcadi A., Aschi M., Bianchi G., and Marinelli F. J. Org. Chem. 70 (2005) 2265