Original one-pot microwave-promoted Hunsdiecker-Suzuki strategy: straightforward access to trans-1,2-diarylethenes from cinnamic acids

Tetrahedron Letters

Volumn 48, Issue 25, 2007, Pages 4347-4351

  Bazin, Marc Antoine ^a   Kihel, Laïla El ^a   Lancelot, Jean Charles ^a   Rault, Sylvain ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

Author keywords

Hunsdiecker bromodecarboxylation; Microwave assisted synthesis; Suzuki cross coupling; trans 1,2 Diarylethenes

Indexed keywords

1,2 DIARYLETHENE DERIVATIVE; CINNAMIC ACID; ETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DRUG ISOLATION; DRUG STRUCTURE; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; SUZUKI REACTION;

EID: 34248662659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.114     Document Type: Article

References (60)

1. Vessières A., Top S., Pigeon P., Hillard E., Boubeker L., Spera D., and Jaouen G. J. Med. Chem. 48 (2005) 3937-3940
2. Sanoh S., Kitamura S., Sugihara K., Kohta R., Ohta S., and Watanabe H. J. Health Sci. 52 (2006) 613-622
3. Heynekamp J.J., Weber W.M., Hunsaker L.A., Gonzales A.M., Orlando R.A., Deck L.M., and Vander Jagt D.L. J. Med. Chem. 49 (2006) 7182-7189
4. Li Y.-Q., Li Z.-L., Zhao W.-J., Wen R.-X., Meng Q.-W., and Zeng Y. Eur. J. Med. Chem. 41 (2006) 1084-1089
5. Ovesna Z., Kozics K., Bader Y., Saiko P., Handler N., Erker T., and Szekeres T. Oncol. Rep. 16 (2006) 617-624
6. Richard N., Porath D., Radspieler A., and Schwager J. Mol. Nutr. Food Res. 49 (2005) 431-442
7. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., and Pezzuto J.M. Science 275 (1997) 218-220
8. Waldeck D.H. Chem. Rev. 91 (1991) 415-436
9. Chaudhuri M.K., and Ganguly S.C. J. Phys. C (Solid State Phys.) 2 (1969) 1560-1565
10. Singh A.K., and Kanvah S. J. Chem. Soc., Perkin Trans. 2 (2001) 395-401
11. Bachelor F.W., Loman A.A., and Snowdon L.R. Can. J. Chem. 48 (1970) 1554-1557
12. Cushman M., Nagarathnam D., Gopal D., Chakraborti A.K., Lin C.M., and Hamel E. J. Med. Chem. 34 (1991) 2579-2588
13. Kim S., Seus P., and Meier H. Eur. J. Org. Chem. 8 (2004) 1761-1764
14. Murias M., Handler N., Erker T., Pleban K., Ecker G., Saiko P., Szekeres T., and Jaeger W. Bioorg. Med. Chem. 12 (2004) 5571-5578
15. Alonso D.A., Fuensanta M., Najera C., and Varea M. J. Org. Chem. 70 (2005) 6404-6416
16. Mirk D., Grassot J.-M., and Zhu J. Synlett (2006) 1255-1259
17. Gooβen L.J., Paetzold J., and Winkel L. Synlett (2002) 1721-1723
18. Arvela R.K., and Leadbeater N.E. J. Org. Chem. 70 (2005) 1786-1790
19. Choi H., Jung I., Song K.H., Song K., Shin D.-S., Kang S.O., and Ko J. Tetrahedron 62 (2006) 9059-9065
20. Farinola G.M., Fiandanese V., Mazzone L., and Naso F. J. Chem. Soc., Chem. Commun. (1995) 2523-2524
21. Molander G.A., and Bernardi C.R. J.Org. Chem. 67 (2002) 8424-8429
22. Cella R., and Stefani H.A. Tetrahedron 62 (2006) 5656-5662
23. Navarro O., Marion N., Mei J., and Nolan S.P. Chem. Eur. J. 12 (2006) 5142-5148
24. Ngwendson J.N., Atemnkeng W.N., Schultze C.M., and Banerjee A. Org. Lett. 8 (2006) 4085-4088
25. Chang S., Na Y., Shin H.J., Choi E., and Jeong L.S. Tetrahedron Lett. 43 (2002) 7445-7448
26. Velder J., Ritter S., Lex J., and Schmalz H.-G. Synthesis 2 (2006) 273-278
27. Bouillon A., Voisin A.S., Robic A., Lancelot J.-C., Collot V., and Rault S. J. Org. Chem. 68 (2003) 10178-10180
28. Voisin A.S., Bouillon A., Berenguer I., Lancelot J.-C., Lesnard A., and Rault S. Tetrahedron 62 (2006) 11734-11739
29. Gérard A.-L., Bouillon A., Mahatsekake C., Collot V., and Rault S. Tetrahedron Lett. 47 (2006) 4665-4669
30. For Hunsdiecker-type halodecarboxylations in various conditions, see:. Johnson R.G., and Ingham R.K. Chem. Rev. 56 (1956) 219-269
31. Berman J.D., and Price C.C. J. Org. Chem. 23 (1958) 102-103
32. Barton D.H.R., Lacher B., and Zard S.Z. Tetrahedron Lett. 26 (1985) 5939-5942
33. Graven A., Jørgensen K.A., Søren D., and Stanczak A. J. Org. Chem. 59 (1994) 3543-3546
34. Chowdhury S., and Roy S. Tetrahedron Lett. 37 (1996) 2623-2624
35. Chowdhury S., and Roy S. J. Org. Chem. 62 (1997) 199-200
36. Naskar D., Chowdhury S., and Roy S. Tetrahedron Lett. 39 (1998) 699-702
37. Homsi F., and Rousseau G. Tetrahedron Lett. 40 (1999) 1495-1498
38. Kuang C., Senboku H., and Tokuda M. Synlett (2000) 1439-1442
39. You H.-W., and Lee K.-J. Synlett (2001) 105-107
40. Roy S.C., Guin C., and Maiti C. Tetrahedron Lett. 42 (2001) 9253-9255
41. Sinha J., Layek S., Mandal G.C., and Bhattacharjee M. Chem. Commun. (2001) 1916-1917
42. Das J.P., and Roy S. J. Org. Chem. 67 (2002) 7861-7864
43. Ye C., and Shreeve J.M. J. Org. Chem. 69 (2004) 8561-8563
44. Kuang C., Senboku H., and Tokuda M. Tetrahedron 61 (2005) 637-642
45. Kuang C., Yang Q., Senboku H., and Tokuda M. Synthesis 8 (2005) 1319-1325
46. Chowdhury S., and Roy S. J. Org. Chem. 62 (1997) 199-200
47. Kuang C., Senboku H., and Tokuda M. Synlett (2000) 1439-1442
48. Das J.P., and Roy S. J. Org. Chem. 67 (2002) 7861-7864
49. Graukroger K., Hadfield J.A., Hepworth L.A., Lawrence N.J., and McGown A.T. J. Org. Chem. 66 (2001) 8135-8138
50. Hadfield, J. A.; McGown, A. T.; Gaukroger, K.; Hepworth, L. A.; Lawrence, N. J. WO 2002049994, 2002.
51. Yamada Y.M.A., Takeda K., Takahashi H., and Ikegami S. Org. Lett. 4 (2002) 3371-3374
52. Arvela R.K., Leadbeater N.E., Sangi M.S., Williams V.A., Granados P., and Singer R.D. J. Org. Chem. 70 (2005) 161-168
53. Katayama H., Nagao M., Ozawa F., Ikegami M., and Arai T. J. Org. Chem. 71 (2006) 2699-2705
54. Dhudshia B., and Thadani A.N. Chem. Commun. (2006) 668-670
55. Babudri F., Cardone A., Cioffi C.T., Farinola G.M., Naso F., and Ragni R. Synthesis 8 (2006) 1325-1332
56. Naskar D., and Roy S. Tetrahedron 56 (2000) 1369-1377
57. Kuang C., Yang Q., Senboku H., and Tokuda M. Tetrahedron 61 (2005) 4043-4052
58. 2S: 246.0724, found: 246.0714.
59. Parrish J.P., Jung Y.C., Shin II S., and Jung K.W. J. Org. Chem. 67 (2002) 7127-7130
60. Chhor R.B., Singh K.A., Nosse B., and Tandon V.K. Synth. Commun. 33 (2003) 2519-2530