Sonogashira reaction on pyridinium N-heteroarylaminides

Tetrahedron Letters

Volumn 52, Issue 15, 2011, Pages 1738-1741

  Córdoba, Marta ^a   Izquierdo, M Luisa ^a   Alvarez Builla, Julio ^a  

^a UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

DABCO; Microwaves; Pyridinium N aminides; Sonogashira

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACETONITRILE; CERIUM OXIDE; N (5 IODOPYRIDIN 2 YL)AMINIDE; PALLADIUM COMPLEX; PYRIDINIUM DERIVATIVE; PYRIDINIUM N HETEROARYLAMINIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; HEATING; MICROWAVE IRRADIATION; SONOGASHIRA REACTION;

EID: 79952539293     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.121     Document Type: Article

References (67)

1. L. Bransma Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques 2004 Elsevier Oxford
2. K. Sonogashira E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 2002 Wiley-Interscience New York 493 529
3. E. Negishi, and L. Anastasia Chem. Rev. 103 2003 1979 2017
4. J.A. Marsden, and M.M. Haley 2nd ed. A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions Vol. 1 2004 Wiley-VCH Weinheim 317 394
5. J.C. Hierso, and H. Doucet Angew. Chem., Int. Ed. 46 2007 834 871
6. R. Chinchilla, and C. Nájera Chem. Rev. 107 2007 874 922
7. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036 1045
8. S. Nara, J. Martinez, C.G. Wermuth, and I. Parrot Synlett 2006 3185 3204
9. M.M. Heravi, and S. Sadjadi Tetrahedron 65 2009 7761 7775
10. S. Roy, S. Roy, B. Neuenswander, D. Hill, and R.C. Larock J. Comb. Chem. 11 2009 1061 1065
11. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem., Int. Ed. 44 2005 4442 4489
12. B.-C. Hong, and R.Y. Nimje Curr. Org. Chem. 10 2006 2191 2225
13. U.H.F. Bunz Chem. Rev. 100 2000 1605 1644
14. C. Weder Chem. Commun. 2005 5378 5389
15. T. Ren Chem. Rev. 108 2008 4185 4207
16. R. Carceller, J.L. García-Navío, M.L. Izquierdo, J. Alvarez-Builla, M. Fajardo, P. Gómez-Sal, and F. Gago Tetrahedron 50 1994 4995 5012
17. C. Burgos, F. Delgado, J.L. García-Navío, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 51 1995 8649 8654
18. V. Martínez-Barrasa, F. Delgado, C. Burgos, J.L. García-Navío, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 56 2000 2481 2490
19. M.J. Reyes, F. Delgado, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 58 2002 8573 8579
20. M.J. Reyes, C. Burgos, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 60 2004 1093 1097
21. R. Castillo, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron Lett. 48 2007 5899 5903
22. R. Castillo, M. Córdoba, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 65 2009 9782 9790
23. M.J. Reyes, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron Lett. 45 2004 8713 8715
24. M.J. Reyes, R. Castillo, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron Lett. 47 2006 6457 6460
25. R. Castillo, M.J. Reyes, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 64 2008 1351 1370
26. M. Córdoba, R.R. Castillo, M.L. Izquierdo, and J. Alvarez-Builla Tetrahedron 66 2010 2624 2632
27. D. García, A.M. Cuadro, J. Alvarez-Builla, and J.J. Vaquero Org. Lett. 6 2004 4175 4178
28. J.-H. Li, and W.-J. Liu Org. Lett. 6 2004 2809 2811
29. J.-H. Li, X.-D. Zhang, and Y.-X. Xie Synthesis 5 2005 804 808
30. J.-H. Li, X.-C. Hu, Y. Liang, and Y.-X. Xie Tetrahedron 62 2006 31 38
31. J.-H. Li, X.-C. Hu, and Y.-X. Xie Tetrahedron Lett. 47 2006 9239 9243
32. J.-H. Li, J.-L. Li, D.-P. Wang, S.-F. Pi, Y.-X. Xie, M.-B. Zhang, and X.-C. Hu J. Org. Chem. 72 2007 2053 2057
33. J.-H. Li, Y. Liang, and Y.-X. Xie J. Org. Chem. 70 2005 4393 4396
34. R. Luque, and D.J. Macquarrie Org. Biomol. Chem. 7 2009 1627 1632
35. 2 (5 mol %) was then added. The mixture was stirred at 40 °C until starting material was no longer detected by TLC. The inorganic salts were filtered off through Celite. The filtrate was evaporated in vacuo and the product was purified by chromatography on silica gel, using ethanol as eluent, and crystallized from a suitable solvent and characterized.
36. 3: C, 79.68; H, 4.83; N, 15.49. Found: C, 79.36; H, 5.09; N, 15.62.
37. A. Loupy, Microwaves in Organic Synthesis 2002 Wiley-VCH Weinheim
38. J. Tierney, and P. Lidstrom Microwave Assisted Organic Synthesis 2004 Blackwell Oxford
39. B.L. Hayes Aldrichim. Acta 37 2004 66 76
40. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250 6284
41. C.O. Kappe, and A. Stadler Microwaves in Organic and Medicinal Chemistry 2005 Wiley-VCH Weinheim
42. C.O. Kappe, and D. Dallinger Nat. Rev. Drug Disc. 5 2006 51 63
43. A. de la Hoz, A. Díaz-Ortiz, A. Moreno, A. Sánchez- Migallón, P. Prieto, J.R. Carrillo, E. Vázquez, M.V. Gómez, and M.A. Herrero Comb. Chem. High Throughput Screening 10 2007 877 902
44. C.O. Kappe Chem. Soc. Rev. 37 2008 1127 1139
45. V. Santagada, F. Frecentese, E. Perissutti, F. Fiorino, B. Severino, and G. Caliendo Mini-Rev. Med. Chem. 9 2009 340 358
46. E. Petricci, M. Radi, F. Corelli, and M. Botta Tetrahedron Lett. 44 2003 9181 9184
47. M. Erdélyi, and A. Gogoll J. Org. Chem. 68 2003 6431 6434
48. H. Huang, H. Liu, H. Jiang, and K. Chen J. Org. Chem. 73 2008 6037 6040
49. 2O: C, 65.18; H, 6.56; N, 15.20. Found: C, 65.39; H, 6.39; N, 15.18.
50. P.A. Grieco, Organic Synthesis in Water 1998 Blackie Academic & Professional London
51. B. Cornils, W.A. Herrmann, Aqueous-phase Organometallic Catalysis, Concepts and Applications 1998 Wiley-VCH Weinheim
52. A. Lubineau, and J. Auge P. Knochel, Modern Solvents in Organic Synthesis 1999 Springer Berlin
53. C. Wolf, and R. Lerebours Org. Biomol. Chem. 2 2004 2161 2164
54. S. Bhattacharya, and S. Sengupta Tetrahedron Lett. 45 2004 8733 8736
55. J. Gil-Moltó, and C. Nájera Eur. J. Org. Chem. 2005 4073 4081
56. B. Liang, M. Dai, J. Chen, and Z. Yang J. Org. Chem. 70 2005 391 393
57. J. Gil-Moltó, S. Karlström, and C. Nájera Tetrahedron 61 2005 12168 12176
58. N. Inoue, O. Sugimoto, and K. Tanji Heterocycles 72 2007 665 671
59. J.T. Guan, T.Q. Weng, G.-A. Yu, and S.H. Liu Tetrahedron Lett. 48 2007 7129 7133
60. B.H. Lipshutz, D.W. Chung, and B. Rich Org. Lett. 10 2008 3793 3796
61. M. Bakherad, A. Keivanloo, B. Bahramian, and M. Hashemi Tetrahedron Lett. 50 2009 1557 1559
62. S. Shi, and Y. Zhang Synlett 2007 1843 1850
63. C.A. Fleckenstein, and H. Plenio Green Chem. 10 2008 563 570
64. A. Komáromi, G.L. Tolnai, and Z. Novák Tetrahedron Lett. 49 2008 7294 7298
65. 3S: C, 69.29; H, 4.00; N, 15.15; S, 11.56. Found: C, 69.65; H, 4.17; N, 15.04; S, 11.29.
66. G. Chen, X. Zhu, J. Cai, and Y. Wan Synth. Commun. 37 2007 1355 1361
67. J.T. Guan, G.-A. Yu, L. Chen, T.Q. Weng, J.J. Yuan, and S.H. Liu Appl. Organomet. Chem. 23 2009 75 77