Chlorotrimethylsilane-mediated friedländer synthesis of polysubstituted quinolines

Synthesis

Volumn , Issue 8, 2007, Pages 1214-1224

  Ryabukhin, Sergey V ^a,b   Volochnyuk, Dmitriy M ^a,c   Plaskon, Andrey S ^b   Naumchik, Vasiliy S ^a   Tolmachev, Andrei A ^b  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Annulation; Chlorotrimethylsilane; o amino aromatic carbonyls; Parallel synthesis; Quinolines

Indexed keywords

ANNULATION; CHLOROTRIMETHYLSILANE; O-AMINO AROMATIC CARBONYLS; PARALLEL SYNTHESIS; QUINOLINES;

SILANES; SYNTHESIS (CHEMICAL); WATER;

AROMATIC COMPOUNDS;

(2,4 DIMETHYLQUINOLIN 3 YL)ACETIC ACID; ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLOROTRIMETHYLSILANE; ETHYL 2 (CHLOROMETHYL) 4 METHYLQUINOLINE 3 CARBOXYLIC ACID; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34247638683     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-966003     Document Type: Article

References (74)

1. Michael, J. P. Nat. Prod. Rep. 2001, 18, 543.
2. (a) Larsen, R. D.; Corley, E. G.; King, A. O.; Carrol, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gautheir, J. Y.; Xiang, Y. B.; Zambony, R. J. J. Org. Chem. 1996, 61, 3398.
3. (b) Chen, Y. J.; Fang, K. C.; Sheu, J.-Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374.
4. (c) Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Chia, M. Eur. J. Med. Chem. 2000, 35, 1021.
5. (a) Kalluraya, B.; Sreenivasa, S. Farmaco 1998, 53, 399.
6. (b) Doube, D.; Blouin, M.; Brideau, C.; Chan, C.; Desmarais, S.; Eitheir, D.; Falgueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Tagari, P.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 1255.
7. Maguire, M. P.; Sheets, K. R.; McVerty, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129.
8. Musser, J. H.; Chakraborty, U. R.; Sciortino, S.; Gordon, R. J.; Khandwala, A.; Neiss, E. S.; Pruss, T. P.; Van Inwegen, R.; Weinrib, I.; Courts, S. M. J. Med. Chem. 1987, 30, 96.
9. Van Inwegen, R. J.; Khandwala, A.; Gordon, R.; Sonnio, P.; Coutts, S.; Joly, S. J. Pharm. Exp. Ther. 1987, 24, 117.
10. Gauthier, J. Y.; Jones, T.; Champion, E.; Charette, L.; Dehaven, R.; Ford-Hatchinson, A. W.; Hoogsteen, K.; Lord, A.; Masson, P.; Piechuta, H.; Pong, S. S.; Springer, J. P.; Therein, M.; Zamboni, R.; Young, R. N. J. Med. Chem. 1990, 33, 2841.
11. Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315; and references therein.
12. (a) Gilchrust, T. L. Heterocyclic Chemistry, 3rd ed.; Adison-Wesley Longman: Essex, 1997, 158-164.
13. (b) Jones, G. In Comprehensive Heterocyclic Chemistry, Vol. 2; Katritzky, A. R.; Rees, A. R., Eds.; Pergamon: Oxford, 1984, 395.
14. A subset of recent work in this area includes: (a)Lindeman, R. J.; Kirollos, S. K. Tetrahedron Lett. 1990, 31, 2689.
15. (b) Strekowski, L.; Lin, S. Y.; Lee, H.; Zhang, Z. Q.; Mason, J. C. Tetrahedron 1998, 54, 1941.
16. (c) Crouse, B.; Begue, J. P.; Daniele, B. D. J. Org. Chem. 2000, 65, 5009.
17. (d) Cho, S. C.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576; and references therein,
18. (e) Amii, H.; Kishkava, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109.
19. (f) Jiang, B.; Yui-Gui, S. J. Org. Chem. 2002, 67, 9449.
20. (g) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, R.; Navenkumar, V.; Nagaiah, K. Synthesis 2003, 1610.
21. (h) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
22. (i) Ishkawa, T.; Manabe, S.; Aikawa, T.; Kudo, T.; Saito, S. Org. Lett. 2004, 6, 2361.
23. (j) Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353.
24. (k) Kobayashi, K.; Yoneda, K.; Miyamoto, K.; Morikawa, O.; Konishi, H. Tetrahedron 2004, 60, 11639.
25. For recent reviews see: (l) Kouznetsov, V. V.; Vargaz Mendez, L. Y.; Melendez Gomez, C. M. Curr. Org. Chem. 2005, 9, 141.
26. (a) Friedlander, P. Ber. Dtsch. Chem. Ges. 1882, 15, 2572.
27. (b) Cheng, C. C.; Yan, S.-J. Org. React. 1982, 28, 37; and references therein.
28. (c) Glaiali, S.; Chelussi, G.; Mudadu, M. S.; Gastuat, M. A.; Thumel, R. P. J. Org. Chem. 2001, 66, 4000.
29. (a) Strekowski, L.; Czamy, A. J. Fluor. Chem. 2000, 104, 281.
30. (b) Hu, Y.-Z.; Zang, G.; Thummel, R. P. Org. Lett. 2003, 5, 2251.
31. Wu, J.; Xia, H. G.; Gao, K. Org. Biomol. Chem. 2006, 4, 126.
32. (a) Arcadi, A.; Chiarini, M.; Di Guespe, S.; Marinelly, F. Synlett 2003, 203.
33. (b) Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett 2004, 963.
34. (c) Varala, R.; Enugala, R.; Adapa, S. R. Synthesis 2006, 3825.
35. (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255.
36. (b) Jia, C. S.; Zhang, Z.; Tu, S. J.; Wang, G. W. Org. Biomol. Chem. 2006, 4, 104.
37. (a) Wang, J.; Fan, X.; Zhang, X.; Han Can, L. Can. J. Chem. 2004, 82, 1192.
38. (b) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, J. V. J. Org. Chem. 2003, 68, 9371.
39. (c) Karthikeyan, G.; Perumal, P. T. J. Heterocycl. Chem. 2004, 41, 1039.
40. For recent examples see: (a) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257.
41. (b) Motokura, K.; Mizugaki, K.; Ebitani, K.; Kiyotomi, K. Tetrahedron Lett. 2004, 45, 6029.
42. For the use of TMSC1 as a condensation agent, see: (a) Ryabukhin, S. V.; Plaskon, A. S.; Tverdokhlebov, A. V.; Tolmachev, A. A. Synth. Commun. 2004, 34, 1483.
43. (b) Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synlett 2004, 2287.
44. (c) Heaney, H.; Papageorgeogu, G.; Wilkins, R. F. Tetrahedron 1997, 53, 2941.
45. For the use of TMSI as a condensation agent, see: (d) Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263.
46. (e) Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Synlett 2003, 858.
47. (f) Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 4129.
48. (g) Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2006, 3715.
49. (h) Ryabukhin, S. V.; Plaskon, A. S.; Ostapchuk, E. N.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2007, 417.
50. For recent examples of derivatives of quinolin-3-ylacetic acid used in lead optimization, see: (a) Wattanasin, S.; Albert, R.; Ehrhardt, C.; Roche, D.; Sabio, N.; Hommel, U.; Welzenbach, K.; Weitz-Schmidt, G. Bioorg. Med. Chem. Lett. 2003, 13, 499.
51. (b) Li, B.; de Laszlo, S. E.; Kamenecka, T. M.; Kopka, I. E.; Durette, P. L.; Lanza, T. Jr.; MacCoss, M.; Tong, S.; Mumford, R. A.; McCauley, E. D.; Van Riper, E.; Schmidt, J. A.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2002, 12, 2141.
52. For the synthesis of derivatives of 3-(carboxymethyl)quinoline-4- carboxylic acid via the Pfitzinger approach see: (a) Buu-Hoi, N. P.; Cagniant, P. Chem. Ber. 1943, 76, 126.
53. For the synthesis of derivatives of (2-chloroquinolin-3-yl)acetic acid see: (b) Meth-Cohn, O.; Rhouati, S.; Tarnowski, B.; Robinson, A. J. Chem. Soc., Perkin Trans. 1 1981, 1537.
54. (a) Bamberg, P.; Johansson, B. Acta Chem. Scand. 1968, 22, 2422.
55. (b) Sakamoto, T.; Kondo, Y.; Masumoto, K.; Yamanaka, H. Heterocycles 1993, 36, 2509.
56. (c) Sakamoto, T.; Katoh, E.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1664.
57. (d) Joergensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557.
58. (a) Kempter, G.; Mobius, G. J. Prakt. Chem. 1966, 34, 298.
59. (b) Meyer, E. v.; Berge, P.; Oehler, R.; Schletter, E. J. Prakt. Chem. 1914, 90, 1.
60. (c) Kauffmann, T.; Woltermann, A. Angew. Chem., Int. Ed. Engl. 1972, 11, 842;
61. Angew. Chem. 1972, 84, 824.
62. (d) Kempter, G.; Hirschberg, S. Chem. Ber. 1965, 98, 419.
63. (e) Fehnel, E. A. J. Org. Chem. 1966, 31, 2899.
64. (f) Kempter, G.; Andertschky, P.; Heilmann, D.; Krausmann, H.; Mictorch, M. Chem. Ber. 1964, 97, 16.
65. (g) Kempter, G.; Zanker, P.; Zurner, H. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300, 829.
66. Anzini, M.; Vomero, S.; Garofalo, A.; Cappelli, A.; Cagnotto, A. Farmaco 1989, 44, 555.
67. Vasse, J.-L.; Levacher, V.; Bourguignon, J.; Dupas, G. Tetrahedron: Asymmetry 2002, 13, 227.
68. (a) Ried, W.; Berg, A.; Schmidt, G. Chem. Ber. 1952, 85, 204.
69. (b) Moon, M. P.; Komin, A. P.; Wolfe, J. F.; Morris, G. F. J. Org. Chem. 1983, 48, 2392.
70. Anzini, M.; Capelli, A.; Vomero, S. Heterocycles 1994, 38, 103.
71. (a) Molina, P.; Conesa, C.; Alias, A.; Arques, A.; Velasco, M. D.; Llamas-Saiz, A. L.; Foces-Foces, C. Tetrahedron 1993, 49, 7599.
72. (b) Kempter, G.; Moebius, G. J. Prakt. Chem. 1966, 34, 298.
73. For similar mechanism of Friedlander condensation, see: Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461.
74. www.enamine.net.