Reactions of 1,4-benzodiazepinic N-nitrosoamidines with tosylmethyl isocyanide: A novel synthesis of midazolam

Synthesis

Volumn , Issue 16, 2004, Pages 2697-2703

  Del Pozo, Carlos ^a   Macías, Alberto ^a   Alonso, Eduardo ^a   González, Javier ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Benzodiazepines; Cyclizations; Heterocycles; Isocyanides; Reductions

Indexed keywords

DERIVATIVES; NEGATIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DESULFONYLATION; HETEROCYCLIC DERIVATIVES; IMIDAZOLE RINGS; IMIDOYL CHLORIDES; MEDICINAL CHEMISTRY; MIDAZOLAM; TOSYLMETHYL ISOCYANIDE;

AROMATIC COMPOUNDS;

1,4 BENZODIAZEPINIC N NITROSOAMIDINE; 3 (4 TOSYL)IMIDAZO[1,5 A][1,4]BENZODIAZEPINE DERIVATIVE; AMIDE; BENZODIAZEPINE DERIVATIVE; CHLORIDE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMIDOYL CHLORIDE; ISOCYANIC ACID DERIVATIVE; MIDAZOLAM; TOSYLMETHYLISOCYANIDE; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ANESTHESIA; ARTICLE; CHEMICAL REACTION KINETICS; DESULFONYLATION; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; SUBSTITUTION REACTION;

EID: 8744304607     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831243     Document Type: Article

References (62)

1. (a) Benzodiazepines Divided: A Multidisciplinary Review, Wiley: New York, 1983.
2. (b) Bock, M. G.; DiPardo, R. M.; Evans, B. E.; Rittle, K. E.; Whitter, W. L.; Veber, D. F.; Anderson, P. S.; Freidinger, R. M. J. Med. Chem. 1989, 32, 13.
3. Sneader, W. In Comprehensive Medicinal Chemistry, Vol. 1; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: London, 1990, 65.
4. (a) Archer, G. A.; Sternbach, L. H. Chem. Rev. 1968, 68, 747.
5. (b) Sharp, J. T. In Comprehensive Heterocyclic Chemistry II, Vol 7; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Amsterdam, 1984, 593.
6. (c) Tucker, H.; Le Count, D. J. In Comprehensive Heterocyclic Chemistry II, Vol 9; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Amsterdam, 1996, 151.
7. For 1,4-benzodizazepines as inhibitors of reverse transcriptase, see: (a) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Brown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494.
8. (b) Merluzzi, V. J.; Hargrave, K. D.; Labadia, M.; Grozinger, K.; Skoog, M.; Wu, J. C.; Shih, C.-K.; Eckner, K.; Hattox, S.; Adams, J.; Rosenthal, A. S.; Faanes, R.; Eckner, R. J.; Koup, R. A.; Sullivan, J. L. Science 1990, 250, 1411.
9. For 1,4-benzodiazepines as antitumor and gene targeted drugs, see: (a) Wang, T.; Lui, A. S.; Cloudsdale, I. S. Org. Lett. 1999, 1, 1835.
10. (b) Novelli, F.; Sparatore, A.; Tasso, B.; Sparatore, F. Bioorg. Med. Chem. Lett. 1999, 9, 3031.
11. (c) Wilson, S. C.; Howard, P. W.; Forrow, S. M.; Hartley, J. A.; Adams, L. J.; Jenkins, T. C.; Kelland, L. R.; Thurston, D. E. J. Med. Chem. 1999, 42, 4028.
12. For 1,4-benzodiazepines as inhibitors of phosphodiesterases PDE4, see: Pascal, Y.; Andrianjara, C. R.; Auclair, E.; Avenel, N.; Bertin, B.; Calvet, A.; Féru, F.; Lardon, S.; Moodley, I.; Ouagued, M.; Payne, A.; Pruniaux, M.-P.; Szilagyi, C. Bioorg. Med. Chem. Lett. 2000, 10, 35.
13. For 1,4-benzodiazepines as potent and selective oxytocin antagonist, see: (a) Evans, B.; Pipe, A.; Clark, L.; Banks, M. Bioorg. Med. Chem. Lett. 2001, 11, 1297.
14. (b) Wyatt, P. G.; Allen, M. J.; Chilcott, J.; Hickin, G.; Miller, N. D.; Woollard, P. M. Bioorg. Med. Chem. Lett. 2001, 11, 1301.
15. For 1,4-benzodiazepines as antagonists of the GPIIb/IIIa receptor, see: (a) Hayes, J. F. Synlett 1999, 865.
16. (b) Andrews, I. P.; Atkins, R. J.; Badham, R. F.; Bellingham, R. K.; Breen, G. F.; Carey, J. S.; Etridge, S. K.; Hayes, J. F.; Hussain, N.; Morgan, D. O.; Share, A. C.; Smith, S. A. C.; Walsgrove, T. C.; Wells, A. S. Tetrahedron Lett. 2001, 42, 4915.
17. For 1,4-benzodiazepines as cholecystokinin (CCK-A) receptor antagonists, see: Sherrill, R. G.; Berman, J. M.; Birkemo, L.; Croom, D. K.; Dezube, L.; Ervin, G. N.; Grizzle, M. K.; James, M. K.; Johnson, M. F.; Queen, K. L.; Rimele, T. J.; Vanmiddlesworth, F.; Sugg, E. E. Bioorg. Med. Chem. Lett. 2001, 11, 1145.
18. For 1,4-benzodiazepines as herbicides, see: (a) Karp, G. M.; Manfredi, M. C.; Guaciaro, M. A.; Ortlip, C. L.; Marc, P.; Szamosi, I. T. J. Agric. Food Chem. 1997, 45, 493.
19. (b) Karp, G. M. J. Org. Chem. 1999, 64, 8156.
20. (a) Vida, J. A. In Medicinal Chemistry; Wolf, M. W.; Burger, A., Eds.; Wiley: New York, 1981, 787.
21. (b) Fryer, R. I. In Comprehensive Heterocyclic Chemistry, Vol 3; Hansch, C., Ed.; Pergamon Press: New York, 1990, 539.
22. (a) Hester, J. B.; Rudzik, A. B.; Kamdar, B. V. J. Med. Chem. 1971, 14, 1078.
23. (b) Schulte, E. Dtsch. Apoth.-Ztg. 1975, 115, 1243.
24. (c) Gilman, N. W.; Holland, B. C.; Fryer, R. I. J. Heterocycl. Chem. 19 77, 14, 1163.
25. (d) Walser, A.; Benjamin, L. E.; Flynn, T.; Mason, C.; Schwartz, R.; Fryer, R. I. J. Org. Chem. 1978, 43, 936.
26. (a) Hester, J. B. Jr.; Duchamp, D.; Chidester, C. G. Tetrahedron Lett. 1971, 1609.
27. (b) Coffen, D. L.; DeNoble, J. P.; Evans, E. L.; Field, G. F.; Fryer, R. I.; Katonak, D. A.; Mandel, B. J.; Sternbach, L. H.; Zally, W. J. J. Org. Chem. 1974, 39, 167.
28. (c) Gall, M.; Hester, J. B. Jr.; Rudzik, A. D.; Lahti, R. A. J. Med. Chem. 1976, 19, 1057.
29. (d) Hester, J. B. Jr. J. Heterocycl. Chem. 1980, 17, 575.
30. (e) Hester, J. B. Jr.; Rudzik, A. D.; Voigtlander, P. F. V. J. Med. Chem. 1980, 23, 392.
31. (f) Hester, J. B. Jr.; Rudzik, A. D.; Voigtlander, P. F. V. J. Med. Chem. 1980, 23, 402.
32. (g) Hester, H. B. Jr.; Rudzik, A. D.; Voigtlander, P. F. V. J. Med. Chem. 1980, 23, 643.
33. (h) Gall, M.; Kamdar, B. V. J. Med. Chem. 1981, 24, 1575.
34. (i) Walser, A.; Fryer, R. I. J. Heterocycl. Chem. 1983, 20, 551.
35. (j) Gall, M.; Kamdar, B. V. J. Heterocycl. Chem. 1988, 25, 1649.
36. (k) Banks, W. L.; Digenis, G. A. Tetrahedron Lett. 1989, 6473.
37. (l) Hester, J. B.; Ludens, J. H.; Emmert, D. E.; West, B. E. J. Med. Chem. 1989, 32, 1157.
38. (m) Walser, A.; Flynn, T.; Mason, C.; Crowley, H.; Maresca, C.; Yaremko, B.; O'Donnel, M. J. Med. Chem. 1991, 34, 1209.
39. Ning, R. Y.; Fryer, R. I.; Madan, P. B.; Sluboski, B. C. J. Org. Chem. 1976, 41, 2724.
40. Walser, A.; Fryer, R. I. J. Org. Chem. 1975, 40, 153.
41. van Leusen, A. M. Lect. Heterocycl. Chem. 1980, 5, S-111.
42. (a) van Nispen, S. P. J. M.; Mensink, C.; van Leusen, A. M. Tetrahedron Lett. 1980, 3723.
43. (b) Massa, S.; Di Santo, R.; Costi, R.; Mai, A.; Artico, M. Med. Chem. Res. 1993, 3, 192.
44. (c) Di Santo, R.; Massa, S.; Artico, M. Il Farmaco 1993, 48, 209.
45. (d) Sisko J.; J. Org. Chem.; 1998, 63: 4529.
46. (e) Mendiola, J.; Minguez, J. M.; Alvarez-Buylla, J.; Vaquera, J. J. Org. Lett. 2000, 2, 3253.
47. (f) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516.
48. (g) Chen, P.; Barrish, J. C.; Iwanowicz, E.; Lin, J.; Bernarz, M. S.; Chen, B.-C. Tetrahedron Lett. 2001, 4293.
49. (h) Barret, A. G. M.; Cramp, S. M.; Hennessy, A.; Procopiou, P. A.; Roberts, R. S. Org. Lett. 2001, 3, 271.
50. (i) Kobayashi, K.; Matsumoto, T.; Irisawa, S.; Yoneda, K.; Morikawa, O.; Konishi, H. Heterocycles 2001, 55, 973.
51. (j) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427.
52. van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
53. (a) Walser, A.; Fryer, R. I.; Sternbach, L. M. J. Heterocycl. Chem. 1974, 11, 619.
54. (b) Walser, A.; Benjamin, L.; Flynn, T.; Mason, C.; Schwartz, R.; Fryer, R. J. Org. Chem. 1978, 43, 936.
55. Bock, M. G.; Di Pardo, R. M.; Evans, B. E.; Rittle, K. E.; Veber, D. F.; Freidinger, R. M.; Hirshfield, J.; Springer, J. P. J. Org. Chem. 1987, 52, 3232.
56. Bakhtiar, C.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1994, 243.
57. Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
58. Addie, M. S.; Taylor, R. J. V. J. Chem. Soc., Perkin Trans. 1 2000, 527.
59. (a) Holton, R. A.; Crouse, D. J.; Williams, A. D.; Kennedy, R. M. J. Org. Chem. 1987, 52, 2317.
60. (b) Adrio, J.; Rivero, M. R.; Carretero, J. C. Angew. Chem. Int. Ed. 2000, 39, 2906.
61. (c) Adrio, J.; Rivero, M. R.; Carretero, J. C. Chem.-Eur. J. 2001, 7, 2435.
62. For a slightly different reduction process using Zn-AcOH and leading to a similar product see earlier reference.13m