The conversion of an aziridine plus a phenyl-substituted amine oxide or aminoether to a benzodiazepine derivative

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8357-8360

  Hancock, Matthew T ^a   Minto, Robert E ^b   Pinhas, Allan R ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

^b MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDE; AZIRIDINE; BENZODIAZEPINE DERIVATIVE; CARBONYL IRON; DIAMINE; ETHER DERIVATIVE; IMINE; LITHIUM DERIVATIVE; PHENYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SUBSTITUTION REACTION;

EID: 0141887613     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.129     Document Type: Article

References (29)

1. Lucet D., LeGall T., Mioskowski C. Angew. Chem., Int. Ed. Engl. 37:1998;2581.
2. Kulkarni Y.S. Aldrichim. Acta. 32:1999;18.
3. Asami M., Sata S., Watanabe H. Chem. Lett. 2000;990.
4. Knof U., von Zelewsky A. Angew. Chem., Int. Ed. Engl. 38:1999;302.
5. del Olmo E., Macho A., Alves M., Lopez J.L., el Banoua F., Munoz E., San Feliciano A. Bioorg. Med. Chem. Lett. 12:2002;2621.
6. Hancock M.T., Pinhas A.R. Organometallics. 21:2002;5155.
7. Chamchaang W., Pinhas A.R. J. Org. Chem. 55:1990;2531.
8. Hancock M.T., Pinhas A.R. Tetrahedron Lett. 44:2003;7125.
9. Li Z., Fernandez M., Jacobsen E.N. Org. Lett. 1:1999;1611.
10. Sabitha G., Babu R.S., Rajkumar M., Yadav J.S. Org. Lett. 3:2002;343.
11. Anand R.V., Pandey G., Singh V.K. Tetrahedron Lett. 43:2002;3975.
12. Fan R.-H., Hou X.-L. J. Org. Chem. 68:2003;726.
13. Kim B.M., So S.M., Choi H.J. Org. Lett. 4:2002;949.
14. Hu X.E. Tetrahedron Lett. 43:2002;5315.
15. O'Brien P., Towers T.D. J. Org. Chem. 67:2002;304. and references cited therein.
16. Xiong C., Wang W., Cai C., Hruby V.J. J. Org. Chem. 67:2002;1399.
17. Chuang T.-H., Sharpless K.B. Org. Lett. 2:2000;3555.
18. Eekhof J.H., Hogeveen H., Kellogg R.M. J. Chem. Soc., Chem. Commun. 1976;657.
19. Pearson A.J., Shively R.J. Jr. Organometallics. 13:1994;578.
20. See for example: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 2002; p. 157; (b) Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: Pacific Grove, CA, 1998; p. 513; (c) Isaacs, N. Physical Organic Chemistry; Longman Scientific: Essex, UK, 1995; p. 475.
21. See for example: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 2002; p. 157; (b) Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: Pacific Grove, CA, 1998; p. 513; (c) Isaacs, N. Physical Organic Chemistry; Longman Scientific: Essex, UK, 1995; p. 475.
22. See for example: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 2002; p. 157; (b) Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: Pacific Grove, CA, 1998; p. 513; (c) Isaacs, N. Physical Organic Chemistry; Longman Scientific: Essex, UK, 1995; p. 475.
23. See for example: (a) Robichaud, A. J.; Fevig, J. M.; Mitchell, I. S.; Lee, T.; Chen, W.; Cacciola, J. Patent Number WO 2002059129; (b) Sabb, A. L.; Vogel, R. L.; Nelson, J. A.; Rosenzweig-Lipson, S. J.; Welmaker, G. S.; Sabalski, J. E.; Smith, M. D.; Chen, A. W.; Antane, M. M.; Raveendranath, P.; Megati, S. Patent Number WO 2002042304; (c) Sabb, A. L.; Vogel, R. L.; Antane, M. M.; Raveendranath, P.; Megati, S.; Smith, M. D.; Nelson, J. A. Patent Number WO 2002062022; (d) Kim, D. H.; Baum, T. J. Med. Chem. 1977, 20, 209.
24. See for example: (a) Robichaud, A. J.; Fevig, J. M.; Mitchell, I. S.; Lee, T.; Chen, W.; Cacciola, J. Patent Number WO 2002059129; (b) Sabb, A. L.; Vogel, R. L.; Nelson, J. A.; Rosenzweig-Lipson, S. J.; Welmaker, G. S.; Sabalski, J. E.; Smith, M. D.; Chen, A. W.; Antane, M. M.; Raveendranath, P.; Megati, S. Patent Number WO 2002042304; (c) Sabb, A. L.; Vogel, R. L.; Antane, M. M.; Raveendranath, P.; Megati, S.; Smith, M. D.; Nelson, J. A. Patent Number WO 2002062022; (d) Kim, D. H.; Baum, T. J. Med. Chem. 1977, 20, 209.
25. See for example: (a) Robichaud, A. J.; Fevig, J. M.; Mitchell, I. S.; Lee, T.; Chen, W.; Cacciola, J. Patent Number WO 2002059129; (b) Sabb, A. L.; Vogel, R. L.; Nelson, J. A.; Rosenzweig-Lipson, S. J.; Welmaker, G. S.; Sabalski, J. E.; Smith, M. D.; Chen, A. W.; Antane, M. M.; Raveendranath, P.; Megati, S. Patent Number WO 2002042304; (c) Sabb, A. L.; Vogel, R. L.; Antane, M. M.; Raveendranath, P.; Megati, S.; Smith, M. D.; Nelson, J. A. Patent Number WO 2002062022; (d) Kim, D. H.; Baum, T. J. Med. Chem. 1977, 20, 209.
26. See for example: (a) Robichaud, A. J.; Fevig, J. M.; Mitchell, I. S.; Lee, T.; Chen, W.; Cacciola, J. Patent Number WO 2002059129; (b) Sabb, A. L.; Vogel, R. L.; Nelson, J. A.; Rosenzweig-Lipson, S. J.; Welmaker, G. S.; Sabalski, J. E.; Smith, M. D.; Chen, A. W.; Antane, M. M.; Raveendranath, P.; Megati, S. Patent Number WO 2002042304; (c) Sabb, A. L.; Vogel, R. L.; Antane, M. M.; Raveendranath, P.; Megati, S.; Smith, M. D.; Nelson, J. A. Patent Number WO 2002062022; (d) Kim, D. H.; Baum, T. J. Med. Chem. 1977, 20, 209.
27. 5 (0. 15 mL, 1.2 mmol), and the amine oxide (0.69 g, 5.0 mmol).
28. Aminoether/iminium reaction procedure: The iminium salt and the gem-aminoether were synthesized as described in Ref. 22. The reaction was run using the same procedure as given in Ref. 7, with aziridine 1 (0.15 g, 1.0 mmol), lithium iodide (0.20 g, 1.5 mmol), and the iminium salt (0.16 g, 1.0 mmol) or gem-aminoether 6 (0.15 g, 1.0 mmol). For the experiment with added base, after the 20 h of stirring and before the work-up, potassium t-butoxide (0.11 g, 1.0 mmol) was added and the reaction mixture was allowed to stir for at least 2 h.
29. Rochin C., Babot O., Dunogues J., Duboudin F. Synthesis. 1986;228.