Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

Tetrahedron Letters

Volumn 54, Issue 17, 2013, Pages 2151-2155

  Rambabu, D ^a   Bhavani, S ^b   Nalivela, Kumara Swamy ^c   Mukherjee, Soumita ^a   Rao, M V Basaveswara ^d   Pal, Manojit ^a  

^a INSTITUTE OF LIFE SCIENCES   (India)

^b K L UNIVERSITY   (India)

^c UNIVERSITY OF HEIDELBERG   (Germany)

^d KRISHNA UNIVERSITY   (India)

Author keywords

Butenolides; Coupling; Cyclization; Pd C

Indexed keywords

3 IODOACRYLIC ACID; ACRYLIC ACID DERIVATIVE; ALKYNE DERIVATIVE; BUTENOLIDE DERIVATIVE; CARBON; COPPER; DIOXANE; LACTONE; LACTONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; GEOMETRY; ONE POT SYNTHESIS; RING OPENING; STEREOCHEMISTRY;

EID: 84875256752     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.040     Document Type: Article

References (44)

1. F. Van der Ohe, and R. Brückner Tetrahedron Lett. 39 1998 909
2. P. Novák, M. Pour, M. Špulák, I. Votruba, and M. Kotora Synthesis 2008 3465
3. R.A. Massy-Westropp, G.D. Reynolds, and T.M. Spotswood Tetrahedron Lett. 18 1966 1939
4. R. Brückner Chem. Commun. 2001 141
5. D.L. Lucetti, E.C.P. Lucetti, M.A.M. Bandeira, H.N.H. Veras, A.H. Silva, L.K.A.M. Leal, A.A. Lopes, V.C.C. Alves, G.S. Silva, G.A. Brito, and G.B. Viana J. Inflamm. 7 2010 60
6. M. Pal, V.R. Veeramaneni, M. Nagabelli, S.R. Kalleda, M. Misra, S.R. Casturi, and K.R. Yeleswarapu Bioorg. Med. Chem. Lett. 13 2008 1639
7. V.R. Pattabiraman, P.S. Padakanti, V.R. Veeramaneni, M. Pal, and K.R. Yeleswarapu Synlett 2002 947
8. S. Padakanti, V.R. Veeramaneni, V.R. Pattabiraman, M. Pal, and K.R. Yeleswarapu Tetrahedron Lett. 43 2002 8715
9. M. Pal, V.V. Rao, P. Srinivas, N. Murali, V. Akhila, M. Premkumar, C.S. Rao, P. Misra, M. Ramesh, and Y.K. Rao Indian J. Chem. 42B 2003 593
10. H.-W. Xu, J.-F. Wang, G.-Z. Liu, G.-F. Hong, and H.-M. Liu Org. Biomol. Chem. 5 2007 1247
11. For a review, see: C. Harcken, T. Berkenbusch, S. Braukmüller, A. Umland, K. Siegel, F. Görth, F. von der Ohe, and R. Brückner Curr. Trends Org. Synth. 1999 153
12. J. Boukouvalas, P.P. Beltrán, N. Lachance, S. Côté, F. Maltais, and M. Pouliot Synlett 2007 219
13. C. Xu, and E. Negishi Tetrahedron Lett. 40 1999 431
14. S. Ma, and Z. Shi J. Org. Chem. 63 1998 6387
15. R. Rossi, F. Bellina, M. Biagetti, and L. Mannina Tetrahedron Lett. 39 1998 7799
16. R. Rossi, F. Bellina, M. Biagetti, and L. Mannina Tetrahedron Lett. 39 1998 7599
17. R. Rossi, F. Bellina, and L. Mannina Tetrahedron Lett. 39 1998 3017
18. R. Rossi, F. Bellina, L. Mannina, and P. Vergamini Tetrahedron 54 1998 135
19. J.A. Marshall, M.A. Wolf, and E.M. Wallace J. Org. Chem. 62 1997 367
20. J.A. Marshall, M.A. Wolf, and E.M. Wallace J. Org. Chem. 60 1995 796
21. J.A. Marshall, M.A. Wolf, and E.M. Wal-lace J. Org. Chem. 61 1996 3238
22. Y. Ogawa, M. Maruno, and T. Wakamatsu Synlett 1995 871
23. T. Sakamoto, M. Annaka, Y. Kondo, and H. Yamanaka Chem. Pharm. Bull. 34 1986 2754
24. N. Menashe, and Y. Shvo Heterocycles 35 1993 611
25. B. Doroh, and G.A. Sulikowski Org. Lett. 8 2006 903
26. H.H. Noriyuki, T. Osaki, M. Nakano, H. Mori, and S. Katsumura J. Org. Chem. 69 2004 7949
27. L. Anastasia, C. Xu, and E. Negishi Tetrahedron Lett. 43 2002 5673
28. N. Furuichi, H. Hara, T. Osaki, H. Mori, and S. Katsumura Angew. Chem. 114 2002 1065 Angew. Chem., Int. Ed. 2002, 41, 1023
29. F. Rossi, A. Bellina, L. Catanese, L. Mannina, and D. Valensin Tetrahedron 56 2000 479
30. M. Biagetti, F. Bellina, A. Carpita, S. Viel, L. Mannina, and R. Rossi Eur. J. Org. Chem. 2002 1063
31. H. Mori, H. Kubo, H. Hara, and S. Katsumura Tetrahedron Lett. 38 1997 5311
32. N.G. Clemo, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 1986 2133
33. M. Biagetti, F. Bellina, A. Carpita, P. Stabile, and R. Rossi Tetrahedron 58 2002 5023
34. F. Bellina, M. Biagetti, A. Carpita, and R. Rossi Tetrahedron 57 2001 2857
35. M.J. Sofia, and J.A. Katzenellenbogen J. Med. Chem. 29 1986 230
36. F. Liu, and E. Negishi J. Org. Chem. 62 1997 8591
37. M. Kotora, and E. Negishi Synthesis 1997 121
38. S. Inack-Ngi, R. Rahmani, L. Commeiras, G. Chouraqui, J. Thibonnet, A. Duchene, M. Abarbri, and J. Parrain Adv. Synth. Catal. 351 2009 779
39. For a review, see: M. Pal Synlett 2009 2896
40. Y.-G. Suh, J.-K. Jung, S.-Y. Seo, K.-H. Min, D.-Y. Shin, Y.-S. Lee, S.-H. Kim, and H.-J. Park J. Org. Chem. 67 2002 4127
41. H. Xie, S. Zhang, H. Li, X. Zhang, S. Zhao, Z. Xu, X. Song, X. Yu, and W. Wang Chem. Eur. J. 18 2012 2230
42. D. Rambabu, S. Bhavani, K.S. Nalivela, M.V.B. Rao, and M. Pal Tetrahedron Lett. 54 2013 1169
43. For a similar Ag-catalyzed cyclization, see: Y. Ogawa, M. Maruno, and T. Wakamatsu Heterocycles 41 1995 2587
44. While cyclization of (Z)-5-phenylpent-2-en-4-ynoic acid has been reported in the presence of pyridine the reaction however required higher temperature and longer reaction time (13 h), see: M. Uchiyama, H. Ozawa, K. Takuma, Y. Matsumoto, M. Yonehara, K. Hiroya, and T. Sakamoto Org. Lett. 8 2006 5517