Highly selective synthesis of 4(5)-aryl-, 2,4(5)-diaryl-, and 4,5-diaryl-1H-imidazoles via Pd-catalyzed direct C-5 arylation of 1-benzyl-1H-imidazole

Tetrahedron

Volumn 64, Issue 26, 2008, Pages 6060-6072

  Bellina, Fabio ^a   Cauteruccio, Silvia ^a   Di Fiore, Annarita ^a   Marchetti, Chiara ^a   Rossi, Renzo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Biologically active compounds; C H bond activation; Direct arylation; Imidazoles; Regioselectivity

Indexed keywords

1 BENZYL 1H IMIDAZOLE; 1 BENZYL 2 (2 NAPHTHYL) 5 PHENYL 1H IMIDAZOLE; 1 BENZYL 2 (4 METHOXYPHENYL) 5 PHENYL 1H IMIDAZOLE; 1 BENZYL 2 [(4 ETHOXYCARBONYL)]PHENYL 2 (4 TOLYL) 1H IMIDAZOLE; 1 BENZYL 2,5 DI(4 METHOXYPHENYL) 1H IMIDAZOLE; 1 BENZYL 4 BROMO 5 (4 METHOXYPHENYL) 1H IMIDAZOLE; 1 BENZYL 4 BROMO 5 (NAPHTHALEN 2 YL) 1H IMIDAZOLE; 1 BENZYL 4 BROMO 5 PHENYL 1H IMIDAZOLE; 1 BENZYL 5 (2 NAPHTHYL) 1H IMIDAZOLE; 1 BENZYL 5 (3,4,5 TRIMETHOXYPHENYL) 1H IMIDAZOLE; 1 BENZYL 5 (4 CHLOROPHENYL) 1H IMIDAZOLE; 1 BENZYL 5 (4 METHOXYPHENYL) 1H IMIDAZOLE; 1 BENZYL 5 (4 METHOXYPHENYL) 2 PHENYL 1H IMIDAZOLE; 1 BENZYL 5 (4 TOLYL) 1H IMIDAZOLE; 1 BENZYL 5 (6 METHOXY 2 NAPHTHYL) 1H IMIDAZOLE; 1 BENZYL 5 [(4 TRIFLUOROMETHYL)PHENYL] 1H IMIDAZOLE; 1 BENZYL 5 PHENYL 1H IMIDAZOLE; 2 (4 METHOXYPHENYL) 4(5) PHENYL 1H IMIDAZOLE; 4(5) (2 NAPHTHYL) 1H IMIDAZOLE; 4(5) (4 METHOXYPHENYL) 1H IMIDAZOLE; 4(5) (4 METHOXYPHENYL) 2 PHENYL 1H IMIDAZOLE; 4(5) (4 TOLYL) 1H IMIDAZOLE; 4(5) PHENYL 1H IMIDAZOLE; 5 (1 BENZYL 1H IMIDAZOL 5 YL)PYRIMIDINE; 5 (1 BENZYL 2 4 TOLYL 1H IMIDAZOL 5 YL) PYRIMIDINE; 5 (1H IMIDAZOL 5 YL)PYRIMIDINE; ETHYL 4 (5 4 TOLYL 1H IMIDAZOL 2 YL)BENZOATE; IMIDAZOLE DERIVATIVE; PALLADIUM; UNINDEXED DRUG;

ARTICLE; ARYLATION; BROMINATION; DRUG SYNTHESIS; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 43849101552     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.051     Document Type: Article

References (64)

1. Ellis G.P., Epstein C., Fitzmaurice C., Golberg L., and Lord G.H. J. Pharm. Pharmacol. 16 (1964) 400
2. Li Y.-K., Hsu H.-S., Chang L.-F., and Chen G. J. Biochem. 123 (1998) 416
3. Kim D.-K., Jang Y., Lee H.S., Park H.-J., and Yoo J. J. Med. Chem. 50 (2007) 3143
4. Suzuki M., Maeda S., Matsumoto K., Ishisuka T., and Iwasawa Y. Chem. Pharm. Bull. 34 (1986) 3111
5. Elliott R.L., Oliver R.M., LaFlamme J.A., Gillaspy M.L., Hammond M., Hank R.F., Maurer T.S., Baker D.L., DaSilva-jardine P.A., Stevenson R.W., Mack C.M., and Cassella J. Bioorg. Med. Chem. Lett. 13 (2003) 3593
6. Liberatore A.-M., Schultz J., Favre-Guilmard C., Pommier J., Chabrièr P.E., and Bigg D. Bioorg. Med. Chem. Lett. 17 (2007) 1746 and references cited therein
7. For reviews on substituted imidazole p38 MAP kinase inhibitors, see:
8. Bellina F., Cauteruccio S., and Rossi R. Tetrahedron 63 (2007) 4571
9. De Luca L. Curr. Med. Chem. 13 (2006) 1
10. Diller D.J., Lin T.H., and Metger A. Curr. Top. Med. Chem. 5 (2005) 953
11. Bolós J. Mini. Rev. Med. Chem. 5 (2005) 857
12. Murry J.A. Curr. Opin. Drug Discov. Devel. 6 (2003) 945
13. Takle A.K., Brown M.J.B., Davies S., Dean D.K., Francis G., Gaiba A., Hird A.W., King F.D., Lovell P.J., Naylor A., Reith A.D., Steadman J.G., and Wilson D.M. Bioorg. Med. Chem. Lett. 16 (2006) 378
14. Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.-H., Marsh K., Warner R., Lee J.Y., Zielinsky-Mozng N., Frost D., Rosenberg S.H., and Sham H.L. J. Med. Chem. 45 (2002) 1697
15. Barta T.E., Stealey M.A., Collins P.W., and Weier R.M. Bioorg. Med. Chem. Lett. 8 (1998) 3443
16. Plummer C.W., Finke P.E., Mills S.G., Wang J., Tong X., Doss G.A., Fong T.M., Lao J.Z., Schaeffer M.-T., Chen J., Shen C.-P., Stribling D.S., Shearman L.P., Strack A.M., and Van der Ploeg L.H.T. Bioorg. Med. Chem. Lett. 15 (2005) 1441
17. For a recent review on the synthesis of 4,5-diaryl-1H-imidazole derivatives, see Ref. 7a.
18. For the synthesis of monosubstituted 4(5)-aryl-1H-imidazoles, see:
19. ten Have R., Huisman M., Meetsma A., and van Leusen A.M. Tetrahedron 53 (1997) 11355
20. Jetter M.C., and Reitz A.B. Synthesis (1998) 829
21. Heerding D.A., Chan G., De Wolf Jr. W.E., Fosberry A.P., Janson C.A., Jaworski D.D., McManus E., Miller W.H., Moore T.D., Payne D.J., Qiu X., Rittenhouse S.F., Slater-Radosti C., Smith W., Takata D.T., Vaidya K.S., Yuan C.C.K., and Huffman W.F. Bioorg. Med. Chem. Lett. 11 (2001) 2061
22. For the synthesis of 2,4(5)-diaryl-1H-imidazoles, see:
23. Li B., Chiu C.K.-F., Hank R.F., Murry J., Roth J., and Tobiassen H. Org. Process Res. Dev. 6 (2002) 682
24. Voets M., Antes I., Schere C., Müller-Vioeira U., Biemel K., Barassin C., Marchais-Oberwinkler S., and Hartmann R.W. J. Med. Chem. 48 (2005) 6632
25. Langhammer I., and Erker T. Heterocycles 65 (2005) 1975
26. Zuliani V., Cocconcelli G., Fantini M., Ghiron C., and Rivara M. J. Org. Chem. 72 (2007) 4551
27. Bellina F., Cauteruccio S., Mannina L., Rossi R., and Viel S. J. Org. Chem. 70 (2005) 3997
28. Bellina F., Cauteruccio S., Mannina L., Rossi R., and Viel S. Eur. J. Org. Chem. (2006) 693
29. Bellina F., Cauteruccio S., and Rossi R. Eur. J. Org. Chem. (2006) 1379
30. Bellina, F.; Calandri, C.; Cauteruccio, S.; Di Fiore, A.; Rossi, R. Book of Abstracts, XXII European Colloquium on Heterocyclic Chemistry, Bari, Italy, Sept 2-6, 2006; SO21;
31. Bellina F., Calandri C., Cauteruccio S., and Rossi R. Eur. J. Org. Chem. (2007) 2147
32. Bellina F., Calandri C., Cauteruccio S., and Rossi R. Tetrahedron 63 (2007) 1970
33. Bellina F., Cauteruccio S., and Rossi R. J. Org. Chem. 72 (2007) 8543
34. For reviews on the transition metal-catalyzed direct arylation reactions, see:
35. Seregin I.V., and Gevorgyan V. Chem. Soc. Rev. 36 (2007) 1173
36. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174
37. Campeau L.-C., Stuart D.R., and Fagnou K. Aldrichimica Acta 40 (2007) 35
38. Campeau L.-C., and Fagnou K. Chem. Commun. (2006) 1253
39. Kakiuchi F., and Chatani N. Adv. Synth. Catal. 345 (2003) 1077
40. Miura M., and Nomura M. Top. Curr. Chem. 219 (2002) 211
41. For some preliminary attempts, see Ref. 16.
42. Bellina, F.; Cauteruccio, S.; Rossi, R. Unpublished results.
43. 3 (2 equiv), see Ref. 15a.
44. For typical examples, see:
45. Cai M., Zhao H., and Huang Y. J. Mol. Catal. A: Chem. 238 (2005) 41
46. Lerma I.C., Cawley M.J., Cloke F.G.N., Arentsen K., Scott J.S., Pearson S.E., Hayler J., and Caddick S. J. Organomet. Chem. 690 (2005) 5841
47. Wang X., Gribkov D.V., and Sames D. J. Org. Chem. 72 (2007) 1476
48. Campeau L.-C., Parisien M., Jean A., and Fagnou K. J. Am. Chem. Soc. 128 (2006) 581
49. 3
50. Ram S., and Spicer L.D. Tetrahedron Lett. 28 (1987) 515
51. Ram S., and Spicer L.D. Synth. Commun. 17 (1987) 415
52. Chen B.-C., Chao S.T., Sundee J.E., Tellew J., and Ahmad S. Tetrahedron Lett. 43 (2002) 1595
53. Juujärvi, P.; Parhi, S.; Karjalainen, J. WO 2004063168, 2004.
54. Chackalamannil, S.; Wang, Y.; Boyle, C.; Stamford, A. W. WO 0224698, 2002.
55. Zawisza A.M., and Muzart J. Tetrahedron Lett. 48 (2007) 6738
56. For typical examples, see:
57. Asproni B., Pau A., Bitti M., Melosu M., Cerri R., Dazzi L., Seu E., Maciocco E., Sanna E., Busonero F., Talani G., Pusceddu L., Altomare C., Trapani G., and Biggio G. J. Med. Chem. 45 (2002) 4655
58. Sisko J., Kassick A.J., Mellinger M., Filan J.J., Allen A., and Olsen M.A. J. Org. Chem. 65 (2000) 1516
59. Frantz D.E., Morency L., Soheili A., Murry J.A., Grabowski E.J.J., and Tillyer R.D. Org. Lett. 6 (2004) 843
60. Revesz L., Blum E., Di Padova F.E., Bihl T., Feifel R., Gram H., Hiestand P., Manning U., and Rucklin G. Bioorg. Med. Chem. Lett. 14 (2004) 3595
61. Revesz L., Di Padova F.E., Buhl T., Feifel R., Gram H., Hiestand P., Manning U., and Zimmerlin A.G. Bioorg. Med. Chem. Lett. 10 (2000) 1261
62. For a multi-step low-yielding synthesis of a 4,5-diaryl-1H-imidazole in which a Pd-catalyzed cross-coupling reaction involving an organometallic reagent was used as a key step, see:. Lipshutz B.H., and Hagen W. Tetrahedron Lett. 33 (1992) 5865
63. Nunami K.-I., Yamada M., Fukui T., and Matsumoto K. J. Org. Chem. 59 (1994) 7635
64. Li B., Chiu C.K.-F., Hank R.F., Murry J., Roth J., and Tobiassen H. Org. Synth. 81 (2005) 105