A remarkable tendency of o-lithio-N-(2-lithiooxyethyl)-N-methyl-aniline to form heterocyclic derivatives by its reaction with dichlorodialkylsilanes or silicon tetrachloride. Synthesis of 2,5,1-benzoxazasilepines and of the silaspiro analogue

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8761-8764

  Kostas, Ioannis D ^a   Screttas, Constantinos G ^a   Raptopoulou, Catherine P ^b   Terzis, Aris ^b  

^a INSTITUTE OF BIOLOGY   (Greece)

^b INSTITUTE OF MATERIALS SCIENCE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030782490     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10345-8     Document Type: Article

References (28)

1. Seguin, M. -C.; Gueyne, J.; Nicolay, J. -F.; Franco, A. (Excymol, Monaco), PCT Int. Appl. WO 96 10,575 1996 [Chem. Abstr. 1996, 125, 67737p].
2. Seguin, M. -C.; Gueyne, J.; Nicolay, J. -F.; Franco, A. (Excymol, Monaco), PCT Int. Appl. WO 96 10,575 1996 [Chem. Abstr. 1996, 125, 67737p].
3. Mamayeva, Ye. A.; Agafonova, O. V.; Negrebetsky, Vad. N.; Shipov, A. G.; Baukov, Yu. I.; Losev, A. S. Khim.-Farm. Zh. 1994, 28(6), 26-29 [Chem. Abstr. 1995, 122, 10104p].
4. Mamayeva, Ye. A.; Agafonova, O. V.; Negrebetsky, Vad. N.; Shipov, A. G.; Baukov, Yu. I.; Losev, A. S. Khim.-Farm. Zh. 1994, 28(6), 26-29 [Chem. Abstr. 1995, 122, 10104p].
5. Tachikawa, M. (Dow Corning Asia, Ltd.), Eur. Pat. Appl. EP 661,290 1995 [Chem Abstr. 1995, 123, 340388c].
6. Tachikawa, M. (Dow Corning Asia, Ltd.), Eur. Pat. Appl. EP 661,290 1995 [Chem Abstr. 1995, 123, 340388c].
7. Selected references of the last ten years: (a) Kim, C. H.; Lee, M. E.; Pae, D. H. Organometallics 1987, 6, 423-424.
8. (b) Sheludyakov, V. D.; Shukyurov, A. Kh.; Kirilina, N. I.; Sokova, N. B.; Kirilin, A. D. Zh. Obshch. Khim. 1988, 58(1), 93-100 [Chem. Abstr. 1989, 110, 23947t].
9. (b) Sheludyakov, V. D.; Shukyurov, A. Kh.; Kirilina, N. I.; Sokova, N. B.; Kirilin, A. D. Zh. Obshch. Khim. 1988, 58(1), 93-100 [Chem. Abstr. 1989, 110, 23947t].
10. (c) Kozyukov, V. P.; Feoktistov, A. E.; Mironov, V. F. ibid. 1988, 58(5), 1056-1060 [Chem. Abstr. 1989, 110, 192967e].
11. (c) Kozyukov, V. P.; Feoktistov, A. E.; Mironov, V. F. ibid. 1988, 58(5), 1056-1060 [Chem. Abstr. 1989, 110, 192967e].
12. (d) Shipov, A. G.; Kramarova, E. P.; Bylikin, S. Yu.; Mamaeva, E. A.; Zaitseva, G. S.; Sergeev, V. N.; Baukov, Yu. I. ibid. 1993, 63(5), 1195-1196 [Chem. Abstr. 1994, 120, 8653g].
13. (d) Shipov, A. G.; Kramarova, E. P.; Bylikin, S. Yu.; Mamaeva, E. A.; Zaitseva, G. S.; Sergeev, V. N.; Baukov, Yu. I. ibid. 1993, 63(5), 1195-1196 [Chem. Abstr. 1994, 120, 8653g].
14. (e) Kramarova, E. P.; Mamaeva, E. A.; Shipov, A. G.; Baukov, Yu. I. ibid. 1993, 63(6), 1435-1436 [Chem. Abstr. 1994, 120, 30808h].
15. (e) Kramarova, E. P.; Mamaeva, E. A.; Shipov, A. G.; Baukov, Yu. I. ibid. 1993, 63(6), 1435-1436 [Chem. Abstr. 1994, 120, 30808h].
16. (f) Walter, S.; Klingebiel, U.; Noltemeyer, M. Chem. Ber. 1992, 125, 783-788.
17. (g) Heinicke, J.; Gehrhus, B. J. Organomet. Chem. 1992, 423, 13-21.
18. (h) Heinicke, J.; Gehrhus, B.; Meinel, S. ibid. 1994, 474, 71-82.
19. (i) Higashiyama, K.; Nakagawa, K.; Takahashi, H. Heterocycles 1995, 47(9), 2007-2017.
20. Two types of benzoxazasilepines or their derivatives have appeared in the previous literature; see: Voss, P.; Meinicke, C.; Popowski, E.; Kelling, H. J. Prakt. Chem. 1978, 320(1), 34-42, and ref. 4d.
21. Analogous ortho-metallation by n-BuLi in ether has previously been reported in the lithiation of N,N-dimethylaniline: Lepley, A. R.; Khan, W. A.; Giumanini, A. B.; Giumanini, A. G. J. Org. Chem. 1966, 31(7), 2047-2051.
22. 2Si: C, 66.22; H, 6.79; N, 8.58. Found: C, 65.82; H, 6.91; N, 8.55.
23. For example see: (a) Brown, T. L.; Ladd, J. A.; Newman, G. N. J. Organomet. Chem. 1965, 3, 1.
24. (b) Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174.
25. For example see: (a) McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805.
26. (b) McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H. R. ibid. 1985, 107, 1810.
27. For a comprehensive review, see: Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1-21.
28. 2 by using SHELXL-93. All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were located by diference maps and their positions were refined isotropically. Crystallographic data (exluding stucture factors) for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Centre.