An efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling of 1-chloroisoquinolines in the formation of 1-alkynyl-3-substituted isoquinolines

Tetrahedron Letters

Volumn 52, Issue 20, 2011, Pages 2566-2570

  Prabakaran, K ^a   Nawaz Khan, F ^a,b   Jin, Jong Sung ^b  

^a VIT UNIVERSITY   (India)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

1 Alkynyl 3 substituted isoquinolines; Copper free; Ruphos; Sonogashira coupling

Indexed keywords

1 CHLOROISOQUINOLINE DERIVATIVE; ALKYNE DERIVATIVE; ISOQUINOLINE DERIVATIVE; LIGAND; PALLADIUM COMPLEX; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; REACTION OPTIMIZATION; REACTION TIME; SONOGASHIRA REACTION; SYNTHESIS;

EID: 79954603150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.040     Document Type: Article

References (33)

1. F. Theil Angew. Chem., Int. Ed. 38 1999 2345
2. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
3. K. Sonogashira B.M. Trost, Comprehensive Organic Synthesis Vol. 3 1999 Pergamon Press Oxford 521
4. H. Kawanami, K. Matsushima, M. Sato, and Y. Ikushima Angew. Chem., Int. Ed. 46 2007 5129
5. W.B. Yi, C. Chi, and X. Wang Eur. J. Org. Chem. 2007 3445
6. J.H. Li, Y. Liang, and Y.X. Xie J. Org. Chem. 70 2005 4393 4396
7. M. Bakherad, A.H. Amin, A. Keivanloo, B. Bahramian, and M. Raeissi Tetrahedron Lett. 51 2010 5653
8. G.W. Kabalka, L. Wang, V. Namboodiri, and R.M. Pagni Tetrahedron Lett. 41 2000 5151
9. Y.-S. Feng, Y.-Y. Li, L. Tang, W. Wu, and H.-J. Xu Tetrahedron Lett. 51 2010 2489
10. D.N. Sawant, P.J. Tambade, Y.S. Wagh, and B.M. Bhanage Tetrahedron Lett. 51 2010 2758
11. J. Athilakshmi, S. Ramanathan, and D.K. Chand Tetrahedron Lett. 49 2008 5286
12. K.G. Thakur, E.A. Jaseer, A.B. Naidu, and G. Sekar Tetrahedron Lett. 50 2009 2865
13. M. Bakherad, A. Keivanloo, B. Bahramian, and S. Mihanparast Tetrahedron Lett. 50 2009 6418
14. M.M. Heravia, A. Kivanloo, M. Rahimzadeh, M. Bakavoli, M. Ghassemzadeh, and B. Neumüllerd Tetrahedron Lett. 46 2005 1607
15. J. Wannberg, Y.A. Sabnis, L. Vrang, B. Samuelsson, A. Karlén, A. Hallberg, and M. Larhed Bioorg. Med. Chem. 14 2006 5303
16. O.S. Miljanic, K.P.C. Vollhardt, and G.D. Whitener Synlett 2003 29
17. H. He, and Y.J. Wu Tetrahedron Lett. 45 2004 3237
18. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422
19. A. Arques, D. Auñon, and P. Molina Tetrahedron Lett. 45 2004 4337
20. A. Komáromi, G.L. Tolnai, and Z. Novák Tetrahedron Lett. 49 2008 7294
21. X. Wang, W. Qin, N. Kakusawa, S. Yasuike, and J. Kurita Tetrahedron Lett. 50 2009 6293
22. N.E. Leadbeater, and B.J. Tominacka Tetrahedron Lett. 44 2003 8653
23. S.S. Tajudeen, and F.N. Khan Synth. Commun. 37 2007 3649
24. P. Manivel, S.M. Roopan, and F.N. Khan J. Chil. Chem. Soc. 53 2008 1609
25. N.T. Patil, F.N. Khan, and Y. Yamamoto Tetrahedron Lett. 45 2004 8497
26. K. Prabakaran, P. Manivel, and F.N. Khan Tetrahedron Lett. 51 2010 4340
27. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, and N. Seik Weng Acta Crystallogr., Sect. E 66 2010 o370
28. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, and N. Seik Weng Acta Crystallogr., Sect. E 66 2010 o488
29. F.N. Khan, P. Manivel, K. Prabakaran, V.R. Hathwar, and A. Mehmet Acta Crystallogr., Sect. E 66 2010 o1056
30. L. Xin-Hua, Z. Jing, Z. An-na, S. Bao-An, Z. Hai-Liang, B. Shan, B. Pinaki, and P. Chun-Xiu Bioorg. Med. Chem. 17 2009 1207
31. B. Heike, W. Julia, A. Christain, and L. Matthias Dev. Comp. Immunol. 30 2006 410
32. 13C NMR, FTIR LC-MS and elemental analysis techniques.
33. 2 requires Mol. Wt.: 354.09. Elemental analysis, calculated: C, 77.85; H, 4.26; Cl, 9.99; N, 7.89. Found: C, 77.77; H, 4.21; N, 7.84.