Novel generation of azomethine imines from α-silylnitrosamines by 1,4- silatropic shift and their cycloaddition

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8849-8853

  Washizuka, Ken Ichi ^a   Nagai, Keiko ^a   Minakata, Satoshi ^a   Ryu, Ilhyong ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; NITROSAMINE; PYRAZOLE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0033544746     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01859-6     Document Type: Article

References (20)

1. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp. 1-176.
2. For reviews, see: (a) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp. 653-732.
3. (b) Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941.
4. (c) Tsuge, O.; Kanemasa, S. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1989; Vol. 45, pp. 231-349.
5. For a review, see: Grashey, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp. 733-814.
6. (a) Komatsu, M.; Ohno, M.; Tsuno, S.; Ohshiro, Y. Chem. Lett. 1990, 575.
7. (b) Iyoda, M.; Sultana, F.; Komatsu, M. Chem. Lett. 1995, 1133.
8. Ohno, M.; Komatsu, M.; Miyata, H.; Ohshiro, Y. Tetrahedron Lett. 1991, 32, 5813.
9. Challis, B.C.; Challis, J. A. In Supplement F: The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives; Patai, S., Ed.; John Wiley & Sons: New York, 1982; Chapter 26.
10. 4 to give α-(trimethylsilyl)benzyl bromide. Thus obtained bromide was substituted with methylamine in methanol to afford N-methyl-α-(trimethylsilyl)benzylamine. Nitrosation of the α-silylamine with sodium nitrite under weakly acidic condition gave 1a. In general, nitrosamines may be mutagenic and carcinogenic. All operations with those compounds should be performed in a well-ventilated hood, and the operator should wear disposable gloves.
11. 1H NMR spectroscopy.
12. Nitrosamines 1b-d were prepared in the same manner for the preparation of 1a (see Ref. 7). Nitrosamine 1e was prepared from commercially available N-nitrosodimethylamine by α-lithiation using lithium diisopropylamide followed by electrophilic substitution with trimethylsilyl chloride.
13. Eckell, A.; George, M. V.; Huisgen, R.; Kende, A. S. Chem. Ber. 1977, 110, 578.
14. In general, primary nitrosamines are unstable and only a few examples are known (see Ref. 6).
15. Kost, A. K.; Grandberg, I. I. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: London, 1966; pp. 347-429.
16. It is well-known that the thermal rearrangement of an N-alkyl-N-nitrosoamide gives an ester via a diazo ester intermediate or a diazo methane derivative, see: (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6008.
17. (b) White, E. H. J. Am. Chem. Soc. 1955, 77, 6011.
18. (c) White, E. H. J. Am. Chem. Soc. 1955, 77, 6014.
19. (d) White, E. H.; Woodcock, D. J. In The Chemistry of Amino Group; Patai, S., Ed.; John Wiley & Sons: New York, 1968; Chapter 8, pp. 440-459.
20. (e) Bieron, J. F.; Dinan, F. J. In The Chemistry of Amides; Patai, S., Ed.; John Wiley & Sons: New York, 1970; Chapter 4, pp. 255-262.