Metalation of 2-trifluoromethylphenothiazine: Synthesis and reactions of trimethylsilyl derivatives

Heterocycles

Volumn 23, Issue 2, 1985, Pages 357-363

  Svensson, Arne ^a   Martin, Arnold R ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85022954422     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/r-1985-02-0357     Document Type: Review

References (20)

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2. A. Hallberg, N.M. Hintermeister, A. Svensson and A.R. Martin, in preparation.
3. B.M. Sutton and B.H. Birnie, J. Med. Chem., 1966, 9, 835.
4. It was necessary to use n-butyllithium at 0-5°C (instead of methyilithium at 25°C) for the preparation of lh because methyilithium (present in an excess) reacted with 1, 2-dibromoethane (halogen-metal exchange) to form methyl bromide. The latter apparently reacted with le to give 1j.
5. H. Gilman, D.A. Shirley and P.R. van Ess, J. Am. Chem. Soc., 1944, 66, 625
6. G. Cauquil, A. Casadevall and E. Casadevall, Bull. Soc. Chim. Fr., 1960, 1049.
7. A. Hallberg and A.R. Martin, Heterocyclic Chem., 1982, 19, 433.
8. A. Hallberg and A.R. Martin, Synth. Commun., 1983, 13, 467.
9. T.G. Jackson and B.J. Warren, J. Heterocyclic Chem., 1972, 9, 399.
10. D. Habich and F. Effenberger, Synthesis, 1979, 841.
11. J.P. Malrieu and B. Pullman, Theoret. Chim. Acta, 1964, 2, 293.
12. C. Bodea and I. Silberg, Advances in Heterocyclic Chemistry, A.R. Katritzky and A.J. Boulton, Eds., Academic Press, New York, vol. 9, 1968, p. 321.
13. The IUPAC conformational notation of (syn-, anti-) (periplanar, clinal) (cf. R..S. Cahn, C. Ingold and V. Prelog, Angew. Chem. Int. Ed., 1966, 5, 385 [in particular, pp. 406-407]) is considered preferable to the earlier, more specialized terminology coined by Malrieu and Pullmanll and will henceforth be used.
14. R.G. Wood, C.H. McCole and G. Williams, Phil. Mag., 1941, 31, 79.
15. J.D. Bell, J.F. Blount, O.V. Briscoe and H.C. Freeman, Chem. Commun., 1968, 24, 1656.
16. D.W. Phelps and A.W. Cordes, J. Heterocyclic Chem., 1976, 13, 625.
17. S.5.C. Chu and V. Napoleone, Acta Crystallogr. (B), 1983, 38, 2506.
18. J.J.H. McDowell, Acta Crystallogr. (B), 1969, 25, 2175.
19. M.C. Malstrom and A.W. Cordes, J. Heterocyclic Chem., 1973, 10, 715.
20. A. Pullman, J. Chim. Phys., 1964, 61, 1666.