Sequential coupling/desilylation-coupling/cyclization in a single pot under Pd/C-Cu catalysis: Synthesis of 2-(hetero)aryl indoles

Organic and Biomolecular Chemistry

Volumn 9, Issue 10, 2011, Pages 3808-3816

  Rao, R Mohan ^a   Reddy Ch, Upendar ^a   Alinakhi, ^a   Mulakayala, Naveen ^a   Alvala, Mallika ^a   Arunasree, M K ^a   Poondra, Rajamohan R ^a   Iqbal, Javed ^a   Pal, Manojit ^a  

^a INSTITUTE OF LIFE SCIENCES   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CLEAVAGES; BOND-FORMING REACTIONS; C-C COUPLING; CU CATALYSIS; FUNCTIONALIZED; IN-VITRO; INDOLE DERIVATIVES; IODOARENES; ONE-POT SYNTHESIS; PHARMACOLOGICAL PROPERTIES; REACTION MIXTURE; REACTION UNDER; SINGLE CRYSTAL X-RAY DATA; TRIETHYLAMINES; TRIMETHYLSILYL;

ACETYLENE; CATALYSIS; SINGLE CRYSTALS;

SYNTHESIS (CHEMICAL);

CARBON; COPPER; INDOLE DERIVATIVE; PALLADIUM; SILICON; SIRT1 PROTEIN, HUMAN; SIRTUIN 1;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; DRUG EFFECT; ENZYME ACTIVATION; HUMAN; METABOLISM; SYNTHESIS;

CARBON; CATALYSIS; COPPER; CYCLIZATION; ENZYME ACTIVATION; HUMANS; INDOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PALLADIUM; SILICON; SIRTUIN 1;

EID: 79955405213     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob01161d     Document Type: Article

References (51)

1. G. W. Gribble, Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, E. F. Scriven, ed.; Pergamon: Oxford, 1996; Vol. 2, pp 207-257
2. W. B. Young A. Kolesnikov R. Rai P. A. Sprengeler E. M. Leahy W. D. Shrader J. Sangalang J. Burgess-Henry J. Spencer K. Elrod L. Cregar Bioorg. Med. Chem. Lett. 2001 11 2253
3. R. L. Mackman H. C. Hui J. G. Breitenbucher B. A. Katz C. Luong A. Martelli D. McGee K. Radika M. Sendzik J. R. Spencer P. A. Sprengeler J. Tario E. Verner J. Wang Bioorg. Med. Chem. Lett. 2002 12 2019
4. W. Chai J. G. Breitenbucher A. Kwok X. Li V. Wong N. I. Carruthers T. W. Lovenberg C. Mazur S. J. Wilson F. U. Axe T. K. Jones Bioorg. Med. Chem. Lett. 2003 13 1767
5. G. W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045
6. J. J. Li and G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon: Oxford UK, 2000; Chapter 3, p 73
7. S. Cacchi G. Fabrizi Chem. Rev. 2005 105 2873
8. G. R. Humphery J. T. Kuethe Chem. Rev. 2006 106 2875
9. Y. Chen N. A. Markina R. C. Larock Tetrahedron 2009 65 8908
10. H. A. Oskooie M. M. Heravi F. K. Behbahani Molecules 2007 12 1438
11. S. S. Palimker P. H. Kumar R. J. Lahoti K. V. Srinivasan Tetrahedron 2006 62 5109
12. C. E. Castro E. J. Gaughn D. C. Owsley J. Org. Chem. 1966 31 4071
13. W.-M. Dai L.-P. Sun D.-S. Guo Tetrahedron Lett. 2002 43 7699
14. T. Sakamoto Y. Kondo H. Yamanaka Heterocycles 1986 24 31
15. T. Sakamoto Y. Kondo S. Iwashita H. Yamanaka Chem. Pharm. Bull. 1987 35 1823
16. Y. Kondo S. Kojima T. Sakamoto J. Org. Chem. 1997 62 6507
17. W.-M. Dai D.-S. Guo L.-P. Sun Tetrahedron Lett. 2001 42 5275
18. A. L. Rodriguez C. Koradin W. Dohle P. Knochel Angew. Chem., Int. Ed. 2000 39 2488
19. M. C. Yasuhara Y. Kanamori M. Kaeko A. Numata Y. Kondo T. Sakamoto J. Chem. Soc., Perkin Trans. 1 1999 529
20. M. G. Saulnier D. B. Fennesson M. S. Deshpande D. M. Vyas Tetrahedron Lett. 1995 36 7841
21. K. Hiroya S. Itoh M. Ozawa Y. Kanamori T. Sakamoto Tetrahedron Lett. 2002 43 1277
22. A. Arcadi G. Bianchi F. Marinelli Synthesis 2004 4 610
23. M. Amjad D. W. Knight Tetrahedron Lett. 2004 45 539
24. D. Yue R. C. Larock Org. Lett. 2004 6 1037
25. M. Layek U. Lakshmi D. Kalita D. K. Barange A. Islam K. Mukkanti M. Pal Beilstein J. Org. Chem. 2009 5 No 46. 10.3762/bjoc.5.46
26. M. Pal V. Subramanian V. R. Batchu I. Dager Synlett 2004 1965
27. M. DÀuria Synth. Commun. 1992 22 2393
28. M. J. Mio L. C. Kopel J. B. Braun T. L. Gadzikwa K. L. Hull R. G. Brisbois C. J. Markworth P. A. Grieco Org. Lett. 2002 4 3199
29. A. Nagy Z. Novak A. Kotschy J. Organomet. Chem. 2005 690 4453
30. C. Yi R. Hua H. Zeng Q. Huang Adv. Synth. Catal. 2007 349 1738
31. K. Sonogashira Y. Tohda N. Hagihara Tetrahedron Lett. 1975 16 4467
32. V. R. Batchu V. Subramanian K. Parasuraman N. K. Swamy S. Kumar M. Pal Tetrahedron 2005 61 9869
33. S. Bhattacharya S. Sengupta Tetrahedron Lett. 2004 45 8733
34. M. Pal Synlett 2009 2896
35. K. S. Kumar S. Chamakuri P. Vishweshwar J. Iqbal M. Pal Tetrahedron Lett. 2010 51 3269
36. Z. Puterová A. Andicsová J. Moncol C. Rabong D. Végh Tetrahedron Lett. 2009 50 4670
37. M. Pal Drug Discovery Today 2009 14 784
38. M. Pal Curr. Med. Chem. 2009 16 3858
39. S. H. Havale M. Pal Bioorg. Med. Chem. 2009 17 1783
40. R. Gupta S. S. Walunj R. K. Tokala K. V. L. Parsa S. K. Singh M. Pal Curr. Drug Targets 2009 10 71
41. A. Kodimuthali S. S. L. Jabaris M. Pal J. Med. Chem. 2008 51 5471
42. M. Pal S. Angaru A. Kodimuthali N. Dhingra Curr. Pharm. Des. 2009 15 1008
43. M. Pal S. Pillarisetti Curr. Med. Chem. -Cardiovascular and Hematological Agents 2007 5 55
44. V. R Veeramaneni M. Pal K. R. Yeleswarapu Tetrahedron 2003 59 3283
45. J. C. Milne P. D. Lambert S. Schenk D. P. Carney J. J. Smith D. J. Gagne L. Jin O. Boss R. B. Perni C. B. Vu J. E. Bemis R. Xie J. S. Disch P. Y. Ng J. J. Nunes A. V. Lynch H. Yang H. Galonek K. Israelian W. Choy A. Iffland S. Lavu O. Medvedik D. A. Sinclair J. M. Olefsky M. R. Jirousek P. J. Elliott Nature 2007 450 712
46. M. Layek A. Reddy M. A. V. D. Rao M. Alvala M. K. Arunasree A. Islam K. Mukkanti J. Iqbal M. Pal Org. Biomol. Chem. 2011 9 1004
47. M. Shaday D. Sinclair Biochem. J. 2007 404 1
48. M. C. Burla R. Caliandro M. Camalli B. Carrozzini G. L. Cascarano L. Caro De C. Giacovazzo G. Polidori R. Spagna J. Appl. Crystallogr. 2005 38 381
49. P. W. Betteridge J. R. Carruthers R. I. Copper K. Prout D. J. Watkin J. Appl. Crystallogr. 2003 36 1487
50. L. L. C. Schrödinger, http://www.Schrödinger.com, (accessed: 24. 04. 2007)
51. F Michel, Sanner. Python: A programming language for software integration and development. J. Mol,. Graphics Mod., 1999, Vol 17, February. pp. 57-61