Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

Synthesis

Volumn , Issue 10, 2011, Pages 1587-1594

  Pereshivko, Olga P ^a   Peshkov, Vsevolod A ^a   Ermolatev, Denis S ^a   Van Hove, Sofie ^a   Van Hecke, Kristof ^a   Van Meervelt, Luc ^a   Van Der Eycken, Erik V ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

2 aminoimidazoles; ring closure; silver; spiro compounds; tandem reaction

Indexed keywords

2-AMINOIMIDAZOLES; GUANIDINE DERIVATIVE; GUANYLATION; HETEROCYCLIZATIONS; PRIMARY AMINES; PROPARGYLAMINES; RING CLOSURE; SPIRO COMPOUNDS; TANDEM REACTION; THREE-COMPONENT COUPLING;

ACETYLENE; KETONES; ORGANIC COMPOUNDS; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL);

SILVER;

AMINE; IMIDAZOLE DERIVATIVE; N (4 METHOXYBENZYL) 1 (2 PHENYLETHYNYL)CYCLOHEXAMINE; PROPARGYLAMINE DERIVATIVE; SILVER; SPIRO 2 AMINOIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 79955872035     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260012     Document Type: Article

References (58)

1. Berlinck R G. S., Burtoloso A C. B., Trindade-Silva A E., Romminger S, Morais R P., Bandeira K, Mizuno C M., Nat. Prod. Rep. 2010 27 1871
2. Berlinck R G. S., Burtoloso A C. B., Kossuga M H., Nat. Prod. Rep. 2008 25 919
3. Berlinck R G. S., Kossuga M H., Nat. Prod. Rep. 2005 22 516
4. Berlinck R G. S., Nat. Prod. Rep. 2002 19 617; and references cited therein
5. For anti-biofilm activity of 2-aminoimidazoles, see:, Huigens R W., Richards J J., Parise G, Ballard T E., Zeng W, Deora R, Melander C, J. Am. Chem. Soc. 2007 129 6966
6. Rogers S A., Melander C, Angew. Chem. Int. Ed. 2008 47 5229
7. Angew. Chem. 2008, 120, 5307
8. Ballard T E., Richards J J., Wolf A L., Melander C, Chem. Eur. J. 2008 14 10745
9. Malamas M S., Erdei J, Gunawan I, Turner J, Hu Y, Wagner E, Fan K, Chopra R, Olland A, Bard J, Jacobsen S, Magolda R L., Pangalos M, Robichaud A J., J. Med. Chem. 2010 53 1146
10. Malamas M S., Erdei J, Gunawan I, Barnes K, Johnson M, Hui Y, Turner J, Hu Y, Wagner E, Fan K, Olland A, Bard J, Robichaud A J., J. Med. Chem. 2009 52 6314
11. Coleman R S., Campbell E L., Carper D J., Org. Lett. 2009 11 2133
12. Nodwell M, Pereira A, Riffell J L., Zimmermann C, Patrick B O., Roberge M, Andersen R J., J. Org. Chem. 2009 74 995
13. Jin Z, Nat. Prod. Rep. 2003 20 584
14. Jin Z, Nat. Prod. Rep. 2005 22 196
15. Jin Z, Nat. Prod. Rep. 2006 23 464
16. Jin Z, Nat. Prod. Rep. 2009 26 382
17. Weinreb S M., Nat. Prod. Rep. 2007 24 931
18. Sullivan J D., Giles R L., Looper R E., Curr. Bioact. Compd. 2009 5 39
19. Hoffmann H, Lindel T, Synthesis 2003 175
20. Koswatta P B., Lovely C J., Nat. Prod. Rep. 2010 28 511; and references cited therein
21. Dunbar D C., Rimoldi J M., Clark A M., Kelly M, Hamann M T., Tetrahedron 2000 56 8795
22. Crews P, Clark D P., Tenney K, J. Nat. Prod. 2003 66 177
23. Hassan W, Edrada R, Ebel R, Wray V, Berg A, Van Soest R, Wiryowidagdo S, Proksch P, J. Nat. Prod. 2004 67 817
24. Fu X, Barnes J R., Do T, Schmitz F J., J. Nat. Prod. 1997 60 497
25. Gross H, Kehraus S, König G M., Woerheide G, Wright A D., J. Nat. Prod. 2002 65 1190
26. Carmely S, Kashman Y, Tetrahedron Lett. 1987 28 3003
27. Carmely S, Ilan M, Kashman Y, Tetrahedron 1989 45 2193
28. Fu X, Schmitz F J., Tanner R S., Kelly-Borges M, [nl]J. Nat. Prod. 1998 61 384
29. Akee R K., Carroll T R., Yoshida W Y., Scheuer P J., Stout T J., Clardy J, J. Org. Chem. 1990 55 1944
30. Carroll A R., Bowden B F., Coll J C., Aust. J. Chem. 1993 46 1229
31. Mancini I, Guella G, Debitus C, Pietra F, Helv. Chim. Acta 1995 78 1178
32. Plubrukarn A, Smith D, Cramer R, Davidson B, J. Nat. Prod. 1997 60 712
33. Edrada R A., Stessman C C., Crews P, J. Nat. Prod. 2003 66 939
34. For original isolation, see:, Kinnel R B., Gehrken H P., Scheuer P J., J. Am. Chem. Soc. 1993 115 3376
35. Kinnel R B., Gehrken H P., Swali R, Skoropowski G, Scheuer P J., J. Org. Chem. 1998 63 3281
36. For structural reassignment, see:, Buchanan M S., Carroll A R., Quinn R J., Tetrahedron Lett. 2007 48 4573
37. For total synthesis, see:, Seiple I B., Su S, Young I S., Lewis C A., Yamaguchi J, Baran P S., Angew. Chem. Int. Ed. 2010 49 1095; and references cited therein
38. For a review on the synthesis of alkaloids from the Oroidin family, see:, Arndt H D., Riedrich M, Angew. Chem. Int. Ed. 2008 47 4785
39. Sivappa R, Koswatta P, Lovely C J., Tetrahedron Lett. 2007 48 5771
40. Sivappa R, Hernandez N M., He Y, Lovely C J., Org. Lett. 2007 9 3861
41. Lovely C J., Du H, He Y, Dias H V. R., Org. Lett. 2004 6 735
42. Iwagawa T, Miyazaki M, Okamura H, Nakatani M, Doe M, Takemura K, Tetrahedron Lett. 2003 44 2533
43. Capon R J., Rooney F, Murray L M., Collins E, Sim A T. R., Rostas J A. P., Butler M S., Carroll A R., J. Nat. Prod. 1998 61 660
44. For synthetic efforts towards dragmacidin E, see:, Feldman K S., Ngernmeesri P, Org. Lett. 2005 7 5449
45. Huntley R J., Funk R L., Org. Lett. 2006 8 4775
46. Feldman K S., Ngernmeesri P, Org. Lett. 2010 12 4502
47. Giles R L., Sullivan J D., Steiner A M., Looper R E., Angew. Chem. Int. Ed. 2009 48 3116
48. Ermolatev D S., Babaev E V., VanderEycken E V., Org. Lett. 2006 8 5781
49. Ermolatev D S., Alifanov V L., Rybakov V B., Babaev E V., VanderEycken E V., Synthesis 2008 2083
50. Ermolatev D S., VanderEycken E V., J. Org. Chem. 2008 73 6691
51. Ermolatev D S., Svidritzky E P., Babaev E V., VanderEycken E, Tetrahedron Lett. 2009 50 5218
52. Modha S G., Mehta V P., Ermolatev D S., Balzarini J, VanHecke K, VanMeervelt L, VanderEycken E, Mol. Diversity 2010 14 767
53. Ermolatev D S., Bariwal J B., Steenackers H P. L., DeKeersmaecker S C. J., VanderEycken E V., Angew. Chem. Int. Ed. 2010 49 9465
54. Ermolatev D S., PhD Thesis Katholieke Universiteit Leuven Belgium 2008
55. For the synthesis of secondary propargylamines, see:, Bariwal J B., Ermolatev D S., VanderEycken E V., Chem. Eur. J. 2010 16 3281
56. 2-coupling, see:, Pereshivko O P., Peshkov V A., VanderEycken E V., Org. Lett. 2010 12 2638
57. During the preparation of this manuscript, the rhodium(II)-catalyzed 6- endo -dig-selective hydroamination of propargylguanidines was reported, see:, Gainer M J., Bennett N R., Takahashi Y, Looper R E., Angew. Chem. Int. Ed. 2011 50 684
58. For the addition of lithium acetylides and n -BuLi to six-membered ketimines, see:, Ma Y, Lobkovsky E, Collum D B., J. Org. Chem. 2005 70 2335