Palladium-catalyzed oxidative heterocyclodehydration-alkoxycarbonylation of 3-yne-1,2-diols: a novel and expedient approach to furan-3-carboxylic esters

Tetrahedron Letters

Volumn 51, Issue 13, 2010, Pages 1663-1665

  Gabriele, Bartolo ^a   Veltri, Lucia ^a   Mancuso, Raffaella ^a   Plastina, Pierluigi ^a   Salerno, Giuseppe ^a   Costa, Mirco ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 YNE 1,2 DIOL DERIVATIVE; ESTER; FURAN CARBOXYLIC ESTER; HETEROCYCLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ALKOXYCARBONYLATION; ARTICLE; CARBONYLATION; HETEROCYCLODEHYDRATION; OXIDATION; SYNTHESIS;

EID: 77049083352     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.054     Document Type: Article

References (78)

1. For very recent examples, see:. Wang W.L., Chai S.C., and Ye Q.-Z. Bioorg. Med. Chem. Lett. 19 (2009) 1080-1083
2. Jeon T.W., Kim C.H., Lee S.K., Shin S., Choi J.H., Kang W., Kim S.H., Kang M.J., Lee E.S., and Jeong T.C. Biomol. Ther. 17 (2009) 318-324
3. Dong Y.Z., Shi Q., Liu Y.N., Wang X., Bastow K.F., and Lee K.-H. J. Med. Chem. 52 (2009) 3586-3590
4. Evidente A., Cristinzio G., Punzo B., Andolfi A., Testa A., and Melck D. Chem. Biodivers. 6 (2009) 328-334
5. Fuji H., Urano E., Futahashi Y., Hamatake M., Tatsumi J., Hoshino T., Morikawa Y., Yamamoto N., and Komano J. J. Med. Chem. 52 (2009) 1380-1387
6. Chandrappa S., Kavitha C.V., Shahabuddin M.S., Vinaya K., Kumar C.S.A., Ranganatha S.R., Raghavan S.C., and Rangappa K.S. Bioorg. Med. Chem. 17 (2009) 2576-2584
7. Amaro M.I., Monasterios M., Avendano M., and Charris J. J. Appl. Toxicol. 29 (2009) 36-41
8. For recent examples, see:. Umeyama T., Takamatsu T., Tezuka N., Matano Y., Araki Y., Wada T., Yoshikawa O., Sagawa T., Yoshikawa S., and Imahori H. J. Phys. Chem. C 113 (2009) 10798-10806
9. Peart P.A., and Tovar J.D. Macromolecules 42 (2009) 4449-4455
10. Gandini A., Silvestre A.J.D., Pascoal Neto C., Souza A.F., and Gomes M. J. Polym. Sci. Pol. Chem. 47 (2009) 295-298
11. Zhang Y., Broekhuis A.A., and Picchioni F. Macromolecules 42 (2009) 1906-1912
12. Nagano T., Mikami Y., Kim S., and Chiba K. Electrochemistry 76 (2008) 874-879
13. Baldwin L.C., Chafin A.P., Deschampes J.R., Hawkins S.A., Wright M.E., Witker D.L., and Prokopuk N. J. Mater. Sci. 43 (2008) 4182-4191
14. For some recent reviews, see:. Van Otterlo W.A.L., and de Koning C.B. Chem. Rev. 109 (2009) 3743-3782
15. Yamamoto Y., Grindnev I.D., Patil N.T., and Jin T. Chem. Commun. 34 (2009) 5075-5087
16. Martins M.A.P., Frizzo C.P., Moreira D.N., Zanatta N., and Bonacorso H.G. Chem. Rev. 108 (2008) 2015-2050
17. Patil N.T., and Yamamoto Y. Chem. Rev. 108 (2008) 3395-3442
18. Cadierno V., and Crochet P. Curr. Org. Synth. 5 (2008) 343-364
19. Kirsch S.F. Synthesis (2008) 3183-3204
20. Shen H.C. Tetrahedron 64 (2008) 3885-3903
21. Shestopalov A.M., Shestopalov A.A., and Rodonovskaya L.A. Synthesis (2008) 1-25
22. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180-3211
23. Balme G., Bouyssi D., and Monteiro N. Heterocycles 73 (2007) 87-124
24. Kirsch S.F. Org. Biomol. Chem. 4 (2006) 2076-2080
25. Moreau C., Belgacem M.N., and Gandini A. Top. Catal. 27 (2004) 11-30
26. Cacchi S., Fabrizi G., and Goggiomani A. Heterocycles 56 (2002) 613-632
27. For very recent examples, see:. Egi M., Azechi K., and Akai S. Org. Lett. 11 (2009) 5002-5005
28. Yoshida M., Al-Amin M., and Shishido K. Synthesis (2009) 2454-2466
29. Briel D., Askar G.B., Ortwein J., and Unverferth K. Pharmazie 64 (2009) 477-478
30. Hu L.X., and Boykin D.W. Synthesis (2009) 2143-2145
31. Saquib M., Husain I., Kumar B., and Shaw A.K. Chem. Eur. J. 15 (2009) 6041-6049
32. Chen C.W., and Luh T.Y. Tetrahedron Lett. 50 (2009) 3263-3265
33. Wang A., Jiang H., and Xu Q. Synlett (2009) 929-932
34. Sydnes L.K., Holmelid B., Sengee M., and Hanstein M. J. Org. Chem. 74 (2009) 3430-3443
35. Cao H., Jiang H., Yao W., and Liu X. Org. Lett. 11 (2009) 1931-1933
36. Ghasemnejad-Bosra H., Faraje M., and Habibzadeh S. Helv. Chim. Acta 92 (2009) 575-578
37. Xiao X.J., and Zhang J.L. Adv. Synth. Catal. 351 (2009) 617-629
38. Zhang M., Jiang H.-F., Neumann H., Beller M., and Dixneuf P.H. Angew. Chem., Int. Ed. 48 (2009) 1681-1684
39. Du X., Song F., Lu Y., Chen H., and Liu Y. Tetrahedron 65 (2009) 1839-1845
40. Li P., Chai Z., Zhao G., and Zhu S.-Z. Tetrahedron 65 (2009) 1673-1678
41. Several synthetic approaches to furan-3-carboxylic esters have been developed; none of these methods, however, involve the direct carbonylation of acyclic precursors. For recent leading examples, see:. Goodman K.B., Bury M.J., Cheung M., Cichy-Knight M.A., Dowdell S.E., Dunn A.K., Lee D., Lieby J.A., Moore M.L., Scherzer D.A., Sha D., Suarez D.P., Murphy D.J., Harpel M.R., Manas E.S., McNulty D.E., Annan R.S., Matico R.E., Schwartz B.K., Trill J.J., Sweitzer T.D., Wang D.-y., Keller P.M., Krawiec J.A., and Jaye M.C. Bioorg. Med. Chem. Lett. 19 (2009) 27-30
42. Barluenga J., Riesgo L., Vicente R., López L.A., and Tomás M. J. Am. Chem. Soc. 130 (2008) 13528-13529
43. Tarwade V., Dmitrenko O., Bach R.D., and Fox J.M. J. Org. Chem. 73 (2008) 8189-8197
44. Blayo A.-L., Gree D., Gree R., and Le Meur S. Adv. Synth. Catal. 350 (2008) 417-476
45. Alizadeh A., Oskueyan Q., Rostamnia S., Ghanbari-Niaki A., and Mohebbi A.R. Synthesis (2008) 2929-2932
46. Terzidis M.A., Tsoleridis C.A., Stephanidou-Stephanatou J., Terzis A., Raptopoulou C.P., and Psycharis V. Tetrahedron 64 (2008) 11611-11617
47. Taguchi Y., Oishi A., and Iida H. Chem. Lett. 37 (2008) 50-51
48. Yoneda Y., Krainz K., Liebner F., Potthast A., Rosenau T., Karakawa M., and Nakatsubo F. Eur. J. Org. Chem. (2008) 475-484
49. Ranu B.C., Laksmikanta A., and Banerjee S. Tetrahedron Lett. 49 (2008) 4613-4617
50. For a recent review on the importance of the development of new atom-economical processes, see:. Trost B.M. Acc. Chem. Res. 35 (2002) 695-705
51. Several molecules incorporating the furan-3-carboxylic ester core have shown interesting pharmacological activities, including antihypertensive, antimicrobial, and anticancer activity. For recent leading examples, see:. Wang J., Zhang H., Yang X., Zhou Y., Wang H., and Bai H. J. Antibiot. 61 (2008) 623-626
52. Moreno-Vargas A.J., Molina L., Carmona A.T., Ferrali A., Robina I., Lambelet M., and Spertini O. Eur. J. Org. Chem. (2008) 2973-2982
53. Seham S.Y. J. Heterocycl. Chem. 44 (2007) 21-27
54. Woods C.R., Hack M.D., Allison B.D., Phuong V.K., Rosen M.D., Morton M.F., Prendergast C.E., Barrett T.D., Shankley N.P., and Rabinowitz M.H. Bioorg. Med. Chem. Lett. 17 (2007) 6905-6909
55. Dominguez C., Smith L., Huang Q., Yuan C., Ouyang X., Cai L., Chen P., Kim J., Harvey T., Syed R., Kim T.-S., Tasker A., Wang L., Zhang M., Coxon A., Bready J., Starnes C., Chen D., Gan Y., Neervannan S., Kumar G., Polverino A., and Kendall R. Bioorg. Med. Chem. Lett. 17 (2007) 6003-6008
56. de Oliveira R.B., de Souza-Fagundes E.M., Siqueira H.A.J., Leite R.S., Donnici C.L., and Zani C.L. Eur. J. Med. Chem. 41 (2006) 756-760
57. Funk O.F., Kettmann V., Drimal J., and Langer T. J. Med. Chem. 47 (2004) 2750-2760
58. 3C{triple bond, long}CMgBr.
59. These conditions (32 atm of CO together with 9 total atm of air, considering that the autoclave was loaded under 1 atm of air) corresponded to 78.0% of CO in air and were outside the explosion limits for CO in air (ca. 16-70% at 18-20 °C and atmospheric pressure, 14.8-71.4% at 100 °C and atmospheric pressure. At higher total pressure, the range of flammability decreases: for example, at 20 atm and 20 °C the limits are ca. 19% and 60%. See: Bartish, C. M.; Drissel, G. M. In: Kirk-Othmer Encyclopedia of Chemical Technology; Grayson, M., Eckroth, D., Bushey, G. J., L. Campbell, L., Klingsberg, A., van Nes, L., Eds., 3rd ed.; Wiley-Interscience: New York, 1978; Vol. 4, p 775.
60. 11
61. 3 (210.27): C, 68.54; H, 8.63. Found: C, 68.53; H, 8.64.
62. 2-catalyzed oxidative carbonylation reactions, see:. Gabriele B., and Salerno G. Cyclocarbonylation. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. II (2002), Wiley-Interscience, New York 2623-2641
63. Gabriele B., Salerno G., Costa M., and Chiusoli G.P. J. Organomet. Chem. 687 (2003) 219-228
64. Gabriele B., Salerno G., Costa M., and Chiusoli G.P. Curr. Org. Chem. 8 (2004) 919-946
65. Gabriele B., Salerno G., and Costa M. Synlett (2004) 2468-2483
66. 2. In: Crich D. (Ed). E-EROS (Electronic Encyclopedia of Reagents for Organic Synthesis) (2006), John Wiley & Sons, Chichester
67. Gabriele B., Salerno G., and Costa M. Top. Organomet. Chem. 18 (2006) 239-272
68. 2-catalyzed oxidative carbonylation reactions, see:. Gabriele B., Mancuso R., Salerno G., Ruffolo G., Costa M., and Dibenedetto A. Tetrahedron Lett. 50 (2009) 7330-7332
69. Della Cà N., Campanini F., Gabriele B., Salerno G., Massera C., and Costa M. Adv. Synth. Catal. 351 (2009) 2423-2432
70. Gabriele B., Mancuso R., Salerno G., Lupinacci E., Ruffolo G., and Costa M. J. Org. Chem. 73 (2008) 4971-4977
71. Gabriele B., Plastina P., Salerno G., Mancuso R., and Costa M. Org. Lett. 9 (2007) 3319-3322
72. Plastina P., Gabriele B., and Salerno G. Synthesis (2007) 3083-3087
73. Gabriele B., Plastina P., Salerno G., and Mancuso R. Synthesis (2006) 4247-4251
74. Gabriele B., Salerno G., Fazio A., and Veltri L. Adv. Synth. Catal. 348 (2006) 2212-2222
75. Gabriele B., Salerno G., Veltri L., Mancuso R., Li Z., Crispini A., and Bellusci A. J. Org. Chem. 71 (2006) 7895-7898
76. Bacchi A., Costa M., Della Cà N., Gabriele B., Salerno G., and Cassoni S. J. Org. Chem. 70 (2005) 4971-4979
77. Gabriele B., Plastina P., Salerno G., and Costa M. Synlett (2005) 935-938
78. Gabriele B., Costa M., Salerno G., and Chiusoli G.P. J. Chem. Soc., Perkin Trans. 1 (1994) 84-87