New synthesis of 1,3-dihydro-1,4-benzodiazepin-2(2H)-ones and 3-amino-1,3-dihydro-1,4-benzodiazepin-2(2H)-ones: Pd-catalyzed cross-coupling of imidoyl chlorides with organoboronic acids

Journal of Organic Chemistry

Volumn 68, Issue 7, 2003, Pages 2844-2852

  Nadin, Alan ^a   Sánchez López, José M ^a   Owens, Andrew P ^a   Howells, Dean M ^a   Talbot, Adam C ^a   Harrison, Timothy ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS;

CATALYST ACTIVITY; ORGANIC ACIDS; ORGANOMETALLICS; PALLADIUM; SYNTHESIS (CHEMICAL);

KETONES;

(1 ETHYLCARBOXAMIDO 5 MORPHOLINYL 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL)CARBAMIC ACID TERT BUTYL ESTER; (1 METHYL 5 PIPERIDINYL 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL)CARBAMIC ACID TERT BUTYL ESTER; (5 AZETIDINYL 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL)CARBAMIC ACID TERT BUTYL ESTER; (5 CHLORO 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL)CARBAMIC ACID TERT BUTYL ESTER; (5 MORPHOLINYL 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL)CARBAMIC ACID TERT BUTYL ESTER; 1,3 DIHYDRO 1,4 BENZODIAZEPIN 2(2H) ONE; 3 AMINO 1,3 DIHYDRO 1,4 BENZODIAZEPIN 2(2H) ONE; 3 AMINO 5 CHLORO 1,4 BENZODIAZEPINE; [2 (3,4 METHYLENEDIOXYPHENYL) 2 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[E][1,4]DIAZEPIN 3 YL] 2,4,5 (TRIFLUOROPHENYL)ACETAMIDE; BENZODIAZEPINE DERIVATIVE; BORONIC ACID DERIVATIVE; CHLORINE DERIVATIVE; IMIDOYLCHLORIDE DERIVATIVE; LACTAM DERIVATIVE; ORGANOBORONIC ACID; ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0242585431     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026860a     Document Type: Article

References (52)

1. Fryer, R. I. Bicyclic Diazepines, The Chemistry of Heterocyclic Compounds; Wiley: New York, 1991; Chapter 7.
2. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Loti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirschfield, J. J. Med. Chem. 1988, 31 2235.
3. Patchett, A. A.; Nargund, R. P. Ann. Rep. Med. Chem. 2000, 35, 289.
4. Castro, J. L.; Broughton, H. B.; Russell, M. G. N.; Rathbone, D.; Watt, A. P.; Ball, R. G.; Chapman, K. L.; Patel, S.; Smith, A. J.; Marshall, G. R.; Matassa, V. G. J. Med. Chem. 1997, 40, 2491 and references therein.
5. Amblard, M.; Daffix, I.; Berge, G.; Calmes, M.; Dodey, P.; Pruneau, D.; Paquet, J.-L.; Luccarini, J.-M.; Belichard, P.; Martinez, J. J. Med. Chem. 1999, 42 (20), 4193-4201.
6. James, G. L.; Goldstein, J. L.; Brown, M. S.; Rawson, T. E.; Somers, T. C.; McDowell, R. S.; Crowley, C. W.; Lucas, B. K.; Levinson, A. D.; Marsters, J. C., Jr. Science (Washington, D.C.) 1993, 260 (5116), 1937-42.
7. Pascal, Y.; Andrianjara, C. R.; Auclair, E.; Avenel, N.; Bertin, B.; Calvet, A.; Feru, F.; Lardon, S.; Moodley, I.; Ouagued, M.; Payne, A.; Pruniaux, M.-P.; Szilagyi, C. Bioorg. Med. Chem. Lett. 2000, 10 (1), 35-38.
8. Selnick, H. G.; Liverton, N. J.; Baldwin, J. J.; Butcher, J. W.; Claremon, D. A.; Elliott, J. M.; Freidinger, R. M.; King, S. A.; Libby, B. E.; McIntyre, C. J.; Pribush, D. A.; Remy, D. C.; Smith, G. R.; Tebben, A. J.; Jurkiewicz, N. K.; Lynch, J. J.; Salata, J. J.; Sanguinetti, M. C.; Siegl, P. K.; Slaughter, D. E.; Vyas, K. J. Med. Chem. 1997, 40, 3865.
9. (a) Athena-Elan: e.g.: Thompson, R. C.; Wilkie, S.; Stack, D. R.; Vanmeter, E. E.; Shi, Q.; Britton, T. C.; Audia, J. E.; Reel, J. K.; Mabry, T. E.; Dressman, B. A.; Cwi, C. L.; Henry, S. S.; Mcdaniel, S. L.; Stucky, R. D.; Porter, W. J. WO 9967221.
10. (b) DuPont: e.g.: Olson, R. E. WO 0192235.
11. (a) Castro Pineiro, J. L.; Churcher, I.; Guiblin, A. R.; Harrison, T.; Kerrad, S.; Madin, A.; Nadin, A. J.; Owens, A. P.; Sparey, T. J.; Teall, M. R.; Williams, S. WO 0190084.
12. (b) Churcher, I.; Ashton, K.; Butcher, J. W.; Clarke, E. E.; Harrison, T.; Lewis, H. D.; Owens, A. P.; Teall, M. R.; Williams, S.; Wrigley, J. D. J. Bioorg. Med. Chem. Lett. 2003, 13, 179.
13. VanDenBerg, C. M.; Kazmi, Y.; Jann, M. W. Drugs Aging 2000, 162, 123-38.
14. (a) Sternbach, L. H. Angew. Chem., Int. Ed. Engl. 1971, 10, 34.
15. (b) Bock, M. G.; DiPardo, R. M.; Evans, B. E.; Rittle, K. E.; Veber, D. F.; Freidinger, R. M. Tetrahedron Lett. 1987, 28, 939.
16. (c) Shi, Y.-J.; Wells, K. M.; Pye, P. J.; Choi, W.-B.; Churchill, H. W. O.; Lynch, J. E.; Maliakal, A.; Sager, J. W.; Rossen, K.; Volante, R. P.; Reider, P. J. Tetrahedron 1999, 55, 909.
17. (d) Bock, M. G.; DiPardo, R. M.; Evans, B. E.; Rittle, K. E.; Veber, D. F.; Freidinger, R. M.; Hirschfield, J.; Springer, J. P. J. Org. Chem. 1987, 52, 3232.
18. (e) Bourrain, S.; Showell, G. A. Synthesis 1994, 5, 505.
19. (f) Sherrill, R. G.; Sugg, E. E. J. Org. Chem. 1995, 60, 730.
20. Bouisset, M.; Bousquet, A.; Heymes, A. DE 3831533 1988.
21. Kobayashi, T.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1985, 26, 3463.
22. Faust, R.; Göbelt, B. Tetrahedron Lett. 1997, 38, 8017.
23. (a) Ukhin, L. Y.; Orlova, Z. I. Zh. Org. Chem. 1987, 23, 2185.
24. (b) Kazankova, M. A.; Trostyanskaya, I. G.; Lutsenko, S. V.; Efimova, I. V.; Beletskaya, I. P. Russ. J. Org. Chem. 1999, 35, 1273.
25. Lin, L.-Y.; Sheng, H.-Y.; Huang, Y.-Z. Synthesis 1991, 235.
26. Jacobi, P. A.; Liu, H. J. Am. Chem. Soc. 1999, 121, 1958.
27. Jacobi, P. A.; Liu, H. Org. Lett. 1999, 1, 341.
28. Yamamoto, S.; Hashiguchi, S.; Miki, S.; Igata, Y.; Watanabe, T.; Shiraishi, M. Chem. Pharm. Bull. 1996, 44, 734.
29. Davis, F. A.; Mohanty, P. K.; Burns, D. M.; Andemichael, Y. W. Org. Lett. 2000, 2, 3901.
30. (a) Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 8131.
31. (b) Occhiato, E. G.; Trabocchi, A.; Guarna, A. J. Org. Chem. 2001, 66, 2459 and references therein.
32. (a) Nicolaou, K. C.; Namoto, K. Chem. Commun. (Cambridge) 1998, 16, 1757-1758.
33. (b) Jiang, J.; DeVita, R. J.; Doss, G. A.; Goulet, M. T.; Wyvratt, M. J. J. Am. Chem. Soc. 1999, 121, 593.
34. Wade, P. C.; Vogt, B. R.; Toeplitz, B.; Puar, M. S.; Gougoutas, J. Z. J. Org. Chem. 1979, 44, 88.
35. Available from Maybridge, Ltd, UK.
36. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
37. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 3724, 3387.
38. Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1992, 57, 379.
39. Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
40. Showell, G. A.; Bourrain, S.; Neduvelil, J. G.; Matassa, V. G.; Matheson, S.; Patel, S.; Smith, A. J.; Chapman, K. L.; Marquis-Omer, D.; Ball, R. G. Med. Chem. Res. 1996, 65, 312-317.
41. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
42. Murata, M.; Oyama, T.; Watanbe, S.; Masuda, Y. Synthesis 2000, 778.
43. A synthesis of 3-amino-3,4-dihydro-1-methyl-1H-1,4-benzodiazepine-2,5-dione is described by Wu et al., WO 9828268.
44. Showell, G. A.; Bourrain, S.; Neduvelil, J. G.; Fletcher, S. R.; Baker, R.; Watt, A. P.; Fletcher, A. E.; Freedman, S. B.; Kemp, J. A.; Marshall, G. R.; Patel, S.; Smith, A. J.; Matassa, V. G. J. Med. Chem. 1994, 37, 719.
45. Reference 12e and references therein.
46. Baldwin, J. J.; Claremon, D. A.; Elliott, J. M.; Liverton, N.; Remy, D. C.; Selnick, H. G. WO 9514473 1995.
47. Reeder, E.; Sternbach, L. H. US patent 3270053, 1966.
48. Wang, J. K. T.; Morgan, J. I.; Spector, S. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 753.
49. Hagashita, Y.; Seno, K.; Myakoshi, M.; Tsushima, T.; Ishihara, Y. JP 07097371, 1995.
50. Shove, L. T.; Chen, S.-W.; Beatty, M.; et al. Bioorg. Med. Chem. 1995, 3, 1547.
51. Owens, A. P.; Nadin, A.; Talbot, A. C.; Harrison, T. Bioorg. Med. Chem. Lett. Submitted for publication.
52. Katritzky, A. R.; et al. J. Org. Chem. 1990, 55, 2206