Direct metalation of heteroaromatic esters and nitriles using a mixed lithium-cadmium base. Subsequent conversion to dipyridopyrimidinones

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 839-847

  Bentabed Ababsa, Ghenia ^a,b   Ely, Sidaty Cheikh Sid ^a   Hesse, Stéphanie ^c   Nassar, Ekhlass ^d   Chevallier, Floris ^a   Nguyen, Tan Tai ^a   Derdour, Aïcha ^b   Mongin, Florence ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ DES SCIENCES ET DE LA TECHNOLOGIE D ORAN MOHAMED BOUDIAF   (Algeria)

^c UNIVERSITÉ DE LORRAINE   (France)

^d Ain Shams University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

2-AMINOPYRIDINE; BACTERICIDAL ACTIVITY; CANDIDA ALBICANS; CARCINOMA CELL LINES; CHEMICAL EQUATIONS; CYANOPYRIDINES; CYTOTOXIC ACTIVITIES; FUNCTIONALIZED; FUNGICIDAL ACTIVITY; FUSARIUM; HUMAN BREAST CARCINOMA CELLS; METALATIONS; METHYLPYRIDINE; ONE POT; PALLADIUM-CATALYZED CROSS-COUPLINGS; ROOM TEMPERATURE; TETRA-HYDROFURAN;

CADMIUM; CELL CULTURE; CYANIDES; ESTERIFICATION; IODINE; PALLADIUM; PYRIDINE; SYNTHESIS (CHEMICAL);

ESTERS;

1 AMINOISOQUINOLINE; 2 AMINO 5 METHYLPYRIDINE; 2 AMINOPYRIMIDINE; 2 CHLORONICOTINATE; CADMIUM; CARBOXYLIC ACID DERIVATIVE; CYANOPYRAZINE; DIPYRIDO[1,2 ALPHA:3',4' DELTA]PYRIMIDIN 11 ONE; DIPYRIDO[1,2 ALPHA:3',4' DELTA]PYRIMIDIN 4 ONE; DIPYRIDO[1,2 ALPHA:3',4' DELTA]PYRIMIDIN 5 ONE; DIPYRIDO[1,2 ALPHA:3',4' DELTA]PYRIMIDIN 8 ONE; DIPYRIDO[1,2 ALPHA:4',3' DELTA]PYRIMIDIN 11 ONE; DIPYRIDOPYRIMIDINONE DERIVATIVE; EHTYL 4 (PYRAZOL 1 YL)NICOTINATE; ESTER DERIVATIVE; ETHYL 3 IODOPICOLINATE; ETHYL 4 (PYRAZOL 1 YL)NICOTINATE; ETHYL 4 IODONICOTINATE; ETHYL IODOPYRIDINECARBOXYLATE DERIVATIVE; IODINE; ISONICOTINIC ACID; LITHIUM; NICOTINIC ACID; NITRILE; PALLADIUM; PYRAZINE; PYRIMIDINE; PYRIMIDINONE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ALBICANS; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; CYTOTOXICITY; FUSARIUM; PROTON TRANSPORT; PSEUDOMONAS AERUGINOSA; ROOM TEMPERATURE; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CADMIUM; CANDIDA ALBICANS; CELL LINE, TUMOR; CROSS-LINKING REAGENTS; CYCLIZATION; ESTERS; FUSARIUM; HEP G2 CELLS; HETEROCYCLIC COMPOUNDS; HUMANS; LITHIUM; METALS; MOLECULAR STRUCTURE; NITRILES; PYRIDINES; PYRIMIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 75749129021     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902385h     Document Type: Article

References (75)

1. (a) Katritzky, A. R. Handbook of Heterocyclic Chemistry, 1st ed.; Pergamon: New York, 1985.
2. (b) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2003; Chapter 6.
3. (a) Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1991, 52, 187-304.
4. (b) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059-4090.
5. (c) Turck, A.; Plé, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489-4505.
6. (d) Schlosser, M.; Mongin, F. Chem. Soc. Rev. 2007, 36, 1161-1172.
7. (e) Chevallier, F.; Mongin, F. Chem. Soc. Rev. 2008, 37, 595-609.
8. (a) Schlecker, W.; Huth, A.; Ottow, E.; Mulzer, J. J. Org. Chem. 1995, 60, 8414-8416.
9. (b) Schlecker, W.; Huth, A.; Ottow, E.; Mulzer, J. Liebigs Ann. Chem. 1995, 1441-1446.
10. (c) Schlecker, W.; Huth, A.; Ottow, E.; Mulzer, J. Synthesis 1995, 1225-1227.
11. Schlosser, M. Pure Appl. Chem. 1988, 60, 1627-1634.
12. Lochmann, L. Eur. J. Inorg. Chem. 2000, 7, 1115-1126.
13. Caubère, P. Chem. Rev. 1993, 93, 2317-2334.
14. Gros, P.; Fort, Y. Eur. J. Org. Chem. 2002, 3375-3383.
15. For reviews, see: (a) Mulvey, R. E. Organometallics 2006, 25, 1060-1075.
16. (b) Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802-3824.
17. (c) Mulvey, R. E. Acc. Chem. Res. 2009, 42, 743-755.
18. (a) Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540.
19. (b) Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514-8515.
20. (c) Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. Angew. Chem., Int. Ed. 2005, 44, 6018-6021.
21. (d) Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2370-2374.
22. (e) Clegg, W.; Dale, S. H.; Harrington, R. W.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2374-2377.
23. (f) Clegg, W.; Dale, S. H.; Drummond, A. M.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. J. Am. Chem. Soc. 2006, 128, 7434-7435.
24. (g) Uchiyama, M.; Kobayashi, Y.; Furuyama, T.; Nakamura, S.; Kajihara, Y.; Miyoshi, T.; Sakamoto, T.; Kondo, Y.; Morokuma, K. J. Am. Chem. Soc. 2008, 130, 472-480.
25. (h) Clegg, W.; Conway, B.; Hevia, E.; McCall, M. D.; Russo, L.; Mulvey, R. E. J. Am. Chem. Soc. 2009, 131, 2375-2384.
26. (a) Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685-7688.
27. (b) Wunderlich, S.; Knochel, P. Chem. Commun. 2008, 6387- 6389.
28. (c) Wunderlich, S. H.; Knochel, P. Org. Lett. 2008, 10, 4705-4707.
29. (d) Mosrin, M.; Knochel, P. Chem.;Eur. J. 2009, 15, 1468-1477.
30. Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837-1840.
31. (a) Uchiyama, M.; Naka, H.; Matsumoto, Y.; Ohwada, T. J. Am. Chem. Soc. 2004, 126, 10526-10527.
32. (b) Garcia-Alvarez, J.; Graham, D. V.; Kennedy, A. R.; Mulvey, R. E.; Weatherstone, S. Chem. Commun. 2006, 30, 3208-3210.
33. (c) Garcia-Alvarez, J.; Hevia, E.; Kennedy, A. R.; Klett, J.; Mulvey, R. E. Chem. Commun. 2007, 2402-2404.
34. (d) Conway, B.; Hevia, E.; García-Álvarez, J.; Graham, D. V.; Kennedy, A. R.; Mulvey, R. E. Chem. Commun. 2007, 5241-5243.
35. (e) Naka, H.; Uchiyama, M.; Matsumoto, Y.; Wheatley, A. E. H.; McPartlin, M.; Morey, J. V.; Kondo, Y. J. Am. Chem. Soc. 2007, 129, 1921-1930.
36. (f) Naka, H.; Morey, J. V.; Haywood, J.; Eisler, D. J.; McPartlin, M.; Garcia, F.; Kudo, H.; Kondo, Y.; Uchiyama, M.; Wheatley, A. E. H. J. Am. Chem. Soc. 2008, 130, 16193-16200.
37. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 1501-1504.
38. Garcia-Álvarez, J.; Kennedy, A. R.; Klett, J.; Mulvey, R. E. Angew. Chem., Int. Ed. 2007, 46, 1105-1108.
39. Usui, S.; Hashimoto,Y.;Morey, J. V.;Wheatley,A. E.H.;Uchiyama, M. J. Am. Chem. Soc. 2007, 129, 15102-15103.
40. (a) L'Helgoual'ch, J.-M.; Bentabed-Ababsa, G.; Chevallier, F.; Yonehara, M.; Uchiyama, M.; Derdour, A.; Mongin, F. Chem. Commun. 2008, 5375-5377.
41. (b) L'Helgoual'ch, J.-M.; Bentabed-Ababsa, G.; Chevallier, F.;Derdour, A.;Mongin, F. Synthesis 2008, 4033-4035.
42. (c) Bentabed-Ababsa, G.; Blanco, F.; Derdour, A.; Mongin, F.; Trécourt, F.; Quéguiner, G.; Ballesteros, R.; Abarca, B. J. Org. Chem. 2009, 74, 163-169.
43. (d) Snégaroff, K.;L'Helgoual'ch, J.-M.;Bentabed-Ababsa,G.;Nguyen, T.T.; Chevallier, F.; Yonehara, M.;Uchiyama, M.;Derdour,A.;Mongin, F. Chem.;Eur. J. 2009, 15, 10280-10290.
44. 2 has to be heated with a heat gun under vacuum for 30 min before each use.
45. (a) Krizan, T. D.; Martin, J. C. J. Org. Chem. 1982, 47, 2681-2682.
46. (b) Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155-6157.
47. Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9276-9287.
48. 2 as electrophile, difunctionalized derivatives concomitantly formed, probably through an homotransmetalation type mechanism: Mallet, M.; Quéguiner, G. Tetrahedron 1985, 16, 3433-3440.
49. (a) Cailly,T.;Fabis,F.;Lemaître, S.; Bouillon,A.;Rault, S. Tetrahedron Lett. 2005, 46, 135-137.
50. (b) Cailly, T.; Fabis, F.; Bouillon, A.; Lemaitre, S.; Sopkova, J.; de Santos,O.;Rault, S. Synlett 2006, 53-56. See also:
51. (c) Cailly, T.; Fabis, F.; Rault, S. Tetrahedron 2006, 62, 5862-5867. An in situ deprotonation-trapping protocol has also been used for the synthesis of the corresponding boronic esters:
52. (d) Hansen, H. M.; Lysén, M.; Begtrup, M.; Kristensen, J. L. Tetrahedron 2005, 61, 9955-9960.
53. (e) Cailly, T.; Lemaître, S.; Fabis, F.;Rault, S. Synthesis 2007, 3247-3251. Note that butyllithium in a mixture of THF and hexane has also been used, albeit in a lowyield, tometalate 4-cyanopyridine at the 2 position:
54. (f) Su, Y.-J.; Ko, C.-W. Chinese Pat. 1616471, 2005.
55. 2NMgCl (2 equiv) in THF at room temperature for 10 min and trapped with iodine to provide the iodide 10 in 77% yield: Shilai, M.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 2001, 442-444.
56. Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7681-7684.
57. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695-709.
58. Begouin, A.; Hesse, S.; Queiroz, M. J. R. P.; Kirsch, G. Synthesis 2006, 2794-2798.
59. Vaidya, N. A.; Panos, C. H.; Kite, A.; Ben Iturrian, W.; De Witt Blanton, C. J. Med. Chem. 1983, 26, 1422-1425.
60. White, D. C.; Greenwood, T. D.; Downey, A. L.; Bloomquist, J. R.; Wolfe, J. F. Bioorg. Med. Chem. Lett. 2004, 5711-5717.
61. Johnson, M.; Li, A.-R.; Liu, J.; Fu, Z.; Zhu, L.; Miao, S.; Wang, X.; Xu, Q.; Huang, A.; Marcus, A.; Xu, F.; Ebsworth, K.; Sablan, E.; Danao, J.; Kumer, J.; Dairaghi, D.; Lawrence, C.; Sullivan, T.; Tonn, G.; Schall, T.; Collins, T.; Medina, J. Bioorg. Med. Chem. Lett. 2007, 3339-3343.
62. (a) Scovill, J.; Blank, E.; Konnick, M.; Nenortas, E.; Shapiro, T. Antimicrob. Agents Chemother. 2002, 46, 882-883.
63. (b) Bhattacharjee, A. K.; Skancky, D. J.; Jennings, B.; Hudson, T. H.; Brendle, J. J.; Werbovetz, K. A. Bioorg. Med. Chem. 2002, 10, 1979-1989.
64. Bhattacharjee, A. K.; Geyer, J. A.; Woodard, C. L.; Kathcart, A. K.; Nichols, D. A.; Prigge, S. T.; Mott, B. T.; Waters, N. C. J. Med. Chem. 2004, 47, 5418-5426.
65. Rylowski, A.; Pucko, W. Acta Pol. Pharm. 1997, 54, 325-330.
66. Bauer, A. W.; Mkriby, W. W.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493.
67. Shannon, M. Heavy Metal Poisoning. In Clinical Management of Poisoning and Drug Overdose, 3rd ed.; Haddad, L. M., Shannon, M., Winchester, J. F., Eds.; W.B. Saunders: Philadelphia, PA, 1998. The use of salts reduces the risk of cadmium absorption.
68. L'Helgoual'ch, J.-M.; Seggio, A.; Chevallier, F.; Yonehara, M.; Jeanneau, E.; Uchiyama, M.; Mongin, F. J. Org. Chem. 2008, 73, 177-183 and references cited therein.
69. 2 · TMEDA was prepared as described: Kedarnath, G.; Kumbhare, L. B.; Jain, V. K.; Phadnis, P. P.; Nethaji, M. Dalton Trans. 2006, 2714-2718.
70. Jones, P.; Kinzel, O.; Llauger Bufi, L.; Muraglia, E.; Pescatore, G.; Torrisi, C. PCT Int. Appl. WO2007138355, 2007.
71. Rodgers, J. D.; Robinson, D. J.; Arvanitis, A. G.; Maduskuie, T. P., Jr.; Shepard, S.; Storace, L.; Wang, H.; Rafalski, M.; Jalluri, R. K.; Combs, A. P. PCT Int. Appl. WO2005105814, 2005.
72. Giblin, G. M. P.; Hall, A.; Hurst, D. N. PCT Int. Appl. WO2005037794, 2005.
73. Storm, O.; Lüning, U. Eur. J. Org. Chem. 2002, 3680-3685.
74. Rylowski, A.; Pucko, W. Acta Pol. Pharm. 1997, 54, 325-330.
75. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112.