Synthesis of cyclopentacarbazolones via palladium-catalyzed annulation of internal alkynes

Synthesis

Volumn 44, Issue 8, 2012, Pages 1268-1278

  Sreenivas, Devanga K ^a   Sandhyarani, Jatoth ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

annulations; cyclopentacarbazolones; estrogen receptors; ligand free synthesis; palladium catalyst

Indexed keywords

ANNULATIONS; CYCLOPENTACARBAZOLONES; ESTROGEN RECEPTOR; LIGAND-FREE; PALLADIUM CATALYST;

CATALYSTS;

ACETYLENE;

2 (4 CHLOROPHENYL) 5 ETHYL 3 PHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 2,3 DIBUTYL 5 ETHYL 8 METHYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 2,3 DIBUTYL 8 METHYL 5 PENTYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 2,3,5 TRIBUTYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 2,5 DIETHYL 3 PHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 2,5 DIETHYL 8 METHYL 3 PHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 3 (4 CHLOROPHENYL) 5 ETHYL 2 PHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 BENZYL 2 ETHYL 3 PHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 BENZYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 BENZYL 2,3 DIPROPYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 BENZYL 8 METHYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 BUTYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 ETHYL 2 METHYL 3 PHENYL DIHYDROCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 ETHYL 2,3 (DI 4 TOLYL)CYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 ETHYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 ETHYL 6,8 DIMETHYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 ETHYL 8 METHYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 5 HEXYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 7 BROMO 5 BUTYL 2,3 (DI 4 TOLYL)CYCLOPENTA[B]CARBAZOL 1(5H) ONE; 7 BROMO 5 BUTYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 8 ETHYL 5 PENTYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; 8 TERT BUTYL 5 ETHYL 2,3 DIPHENYLCYCLOPENTA[B]CARBAZOL 1(5H) ONE; ALKYNE DERIVATIVE; CARBAZOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 84859239039     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290807     Document Type: Article

References (64)

1. Wu Y.-T, Hayama T, Baldridge K K., Linden A, Siegel J S., J. Am. Chem. Soc. 2006 128 6870
2. Ogliaruso M A., Romanelli M G., Becker E I., Chem. Rev. 1965 65 261
3. Tius M A., Eur. J. Org. Chem. 2005 2193
4. Alcaide B, Almendros P, Eur. J. Org. Chem. 2004 3377
5. Vaidya T, Eisenberg R, Frontier A J., ChemCatChem 2011 3 1531
6. Leboeuf D, Huang J, Gandon V, Fronteir A L., Angew. Chem. Int. Ed. 2011 50 10981
7. Tyagi P, Venkateswararao A, Thomas K R. J., J. Org. Chem. 2011 76 4571
8. Cai Z, Harmata M, Org. Lett. 2010 12 5668
9. Andrew T L., Cox J R., Swager T M., Org. Lett. 2010 12 5302
10. Oesterling I, Mullen K, J. Am. Chem. Soc. 2007 129 4595
11. Lor M, Thielemans J, Viaene L, Cotlet M, Hofkens J, Weil T, Hampel C, Mullen K, Verhoeven J W., Auweraer M V., De Schryver F C., J. Am. Chem. Soc. 2002 124 9918
12. Dorta E, Diaz-Marrero A R., Cueto M, D'Croz L, Mate J L., Darias J, Org. Lett. 2004 6 2229
13. Shibata T, Yamashita K, Ishida H, Takagi K, Org. Lett. 2001 3 1217
14. Gamba A, Gandolfi R, Oberti R, Sardone N, Tetrahedron 1993 49 6331
15. Jikyo T, Eto M, Harano K, Tetrahedron 1999 55 6051
16. Rainier J D., Imbriglio J E., Org. Lett. 1999 1 2037
17. Ding L, Ying H.-Z, Zhou Y, Lei T, Pei J, Org. Lett. 2010 12 5522
18. Gagnier S V., Larock R C., J. Am. Chem. Soc. 2003 125 4804
19. Talaz O, Glin I, Göksu S, Saracoglu N, Bioorg. Med. Chem. 2009 17 6583
20. Larock R C., Emrich D E., J. Organomet. Chem. 2004 689 3756
21. Vasilyev A V., Walspurger S, Paleb P, Sommer J, Tetrahedron Lett. 2004 45 3379
22. Coyanis E M., Panayides J.-E, Fernandes M A., DeKoning C B., Van Otterlo W A. L., J. Organomet. Chem. 2006 691 5222
23. Larock R C., Yian Q, Pletnev A A., J. Am. Chem. Soc. 1999 121 3238
24. Leoni L M., Hamel E, Genini D, Hsiencheng S, Carrera C J., Cottam H B., Carson D A., J. Natl. Cancer Inst. 2000 92 217
25. Kerr D J., Hamel E, Jung M K., Flynn B L., Bioorg. Med. Chem. 2007 15 3290
26. Jourdan G P., Dreikom B A., Hackler R E., Hall H R., Arnold W R., In Synthesis and Chemistry of Agrochemicals II ACS Symposium Series 566 American Chemical Society Washington DC 1991
27. Ahn J H., Shin M S., Jung S H., Kang S K., Kim K R., Rhee S D., Jung W H., Yang S D., Kim S J., Woo J R., Lee J H., Cheon H G., Kim S S., J. Med. Chem. 2006 49 4781
28. Ahn J H., Shin M S., Jung S H., Kim J A., Kim H M., Kim S H., Kang S K., Kim K R., Rhee S D., Park S D., Lee J H., Cheon H G., Kim S S., Bioorg. Med. Chem. Lett. 2007 17 5239
29. Anstead G M., Altenbach R J., Wilson S R., Katzenellenbogen J A., J. Med. Chem. 1998 31 1316
30. Goodwin S, Smith A F., Horning E C., J. Am. Chem. Soc. 1959 81 1903
31. Cho S H., Yoon J, Chang S, J. Am. Chem. Soc. 2011 133 5996
32. Alcaide B, Almendros P, Alonso J M., Quiros T, Gadzinski P, Adv. Synth. Catal. 2011 353 1871
33. Knölker H.-J, Chem. Lett. 2009 38 8
34. Knölker H.-J, Reddy K R., In The Alkaloids Vol. 65 Cordell G A. Elsevier Science Amsterdam 2008 1-430
35. Knölker H.-J, Reddy K R., Chem. Rev. 2002 102 4303
36. Chakraborty D P., Das K C., Chowdhury B K., J. Org. Chem. 1971 36 725
37. Archer S, Ross B S., Pica-Mattoccia L, Cioli D, J. Med. Chem. 1987 30 1204
38. Ayats C, Soley R, Albericio F, Alvarez M, Org. Biomol. Chem. 2009 5 860
39. Laronze M, Boisbrun M, Lonce S, Pfeiffer B, Renard P, Lozach O, Meijer L, Lansiuax A, Bailly M, Sapi J, Laronze J.-Y, Bioorg. Med. Chem. 2005 6 2263
40. Gruner K K., Knölker H.-J, Org. Biomol. Chem. 2008 6 3902
41. Molina P, Fresneda P M., Almendros P, Tetrahedron 1993 49 1223
42. Lebold T P., Kerr M A., Org. Lett. 2007 9 1883
43. Basavaiah D, Lenin V, Eur. J. Org. Chem. 2010 5650
44. Kuninobu Y, Matsuki T, Takai K, Org. Lett. 2010 12 2948
45. Morimoto T, Yamasaki K, Hirano A, Tsutsumi K, Kagawa N, Kakiuchi K, Harada Y, Fukumoto Y, Chatani N, Nishioka T, Org. Lett. 2009 11 1777
46. Hatjiarapoglou L, Varvoglis A, Alcock N W., Pike G A., J. Chem. Soc., Perkin Trans. 1 1988 2839
47. Vicente J, Abad J.-A, Lopez-Pelaez B, Martinez-Viviente E, Organometallics 2002 21 58
48. Pletnev A A., Tian Q, Larock R C., J. Org. Chem. 2002 67 9276
49. Bo C, Xingang X, Jiangping L, Qiaoling W, Jiyong Z, Shouchu T, Xuegong S, Xinfu P, Synlett 2006 259
50. Alonso D A., Najera C, Pacheco M C., Adv. Synth. Catal. 2002 344 172
51. Zhang H, Larock R C., J. Org. Chem. 2002 67 9318
52. Zhang H, Larock R C., J. Org. Chem. 2003 68 5132
53. Vasilyev A V., Walspurger S, Paleb P, Sommera J, Tetrahedron Lett. 2004 45 3379
54. Chang K.-J, Rayabarapu D K., Cheng C.-H, Org. Lett. 2003 5 3963
55. Larock R C., Doty M J., Cacchi S, J. Org. Chem. 1993 58 4579
56. Zeni G, Larock R C., Chem. Rev. 2006 106 4644
57. Gevorgyan V, Quan L G., Yamamoto Y, Tetrahedron Lett. 1999 40 4089
58. Wang S, Zhu Y, Wang Y, Lu P, Org. Lett. 2009 11 2615
59. Waldo J P., Zhang X, Shi F, Larock R C., J. Org. Chem. 2008 73 6679
60. Zang J, Yang F, Wu Y, Appl. Organomet. Chem. 2011 25 675
61. Leng Y, Yang F, Wei K, Wu Y, Tetrahedron 2011 66 1244
62. Chaitanya T K., Nagarajan R, Org. Biomol. Chem. 2011 9 4662
63. Chaitanya T K., Prakash K S., Nagarajan R, Tetrahedron 2011 67 6934
64. 1. Unit cell parameters: a = 7.9184(6), b = 10.4371(7), c = 12.1136(10), = 76.338(6), = 83.212(7), = 77.905(6), space group P 1. The CCDC deposition numbers of compounds 3a, r, s are 840023, 840025, and 840024, respectively. Further data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].