Ethylation by ethyl ethers in the presence of organometallic bases: Reactions of hydrocycloalk[b]indoles

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 639-640

  Naruse, Yuji ^a   Ito, Yoshitaka ^a   Inagaki, Satoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0033593401     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813080     Document Type: Article

References (24)

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2. Ziegler, K.; Gellert, H.-G. Justus Liebigs Ann. Chem. 1950, 567, 185. Bartlett, P. D.; Friedman, S.; Stiles, M. J. Am. Chem. Soc. 1963, 75, 1771. Gilman, H.; Haubein, A. H. J. Org. Chem. 1954, 19, 1034. Spialter, L.; Harris, C. W. J. Org. Chem. 1966, 31, 4263. Suga, K.; Watanabe, S.; Tsu, P. P. Aust. J. Chem. 1968, 21, 2341-2344. Carnahan, J. C.; Closson, W. D. J. Org. Chem. 1972, 37, 4469.
3. Ziegler, K.; Gellert, H.-G. Justus Liebigs Ann. Chem. 1950, 567, 185. Bartlett, P. D.; Friedman, S.; Stiles, M. J. Am. Chem. Soc. 1963, 75, 1771. Gilman, H.; Haubein, A. H. J. Org. Chem. 1954, 19, 1034. Spialter, L.; Harris, C. W. J. Org. Chem. 1966, 31, 4263. Suga, K.; Watanabe, S.; Tsu, P. P. Aust. J. Chem. 1968, 21, 2341-2344. Carnahan, J. C.; Closson, W. D. J. Org. Chem. 1972, 37, 4469.
4. Ziegler, K.; Gellert, H.-G. Justus Liebigs Ann. Chem. 1950, 567, 185. Bartlett, P. D.; Friedman, S.; Stiles, M. J. Am. Chem. Soc. 1963, 75, 1771. Gilman, H.; Haubein, A. H. J. Org. Chem. 1954, 19, 1034. Spialter, L.; Harris, C. W. J. Org. Chem. 1966, 31, 4263. Suga, K.; Watanabe, S.; Tsu, P. P. Aust. J. Chem. 1968, 21, 2341-2344. Carnahan, J. C.; Closson, W. D. J. Org. Chem. 1972, 37, 4469.
5. Ziegler, K.; Gellert, H.-G. Justus Liebigs Ann. Chem. 1950, 567, 185. Bartlett, P. D.; Friedman, S.; Stiles, M. J. Am. Chem. Soc. 1963, 75, 1771. Gilman, H.; Haubein, A. H. J. Org. Chem. 1954, 19, 1034. Spialter, L.; Harris, C. W. J. Org. Chem. 1966, 31, 4263. Suga, K.; Watanabe, S.; Tsu, P. P. Aust. J. Chem. 1968, 21, 2341-2344. Carnahan, J. C.; Closson, W. D. J. Org. Chem. 1972, 37, 4469.
6. Ziegler, K.; Gellert, H.-G. Justus Liebigs Ann. Chem. 1950, 567, 185. Bartlett, P. D.; Friedman, S.; Stiles, M. J. Am. Chem. Soc. 1963, 75, 1771. Gilman, H.; Haubein, A. H. J. Org. Chem. 1954, 19, 1034. Spialter, L.; Harris, C. W. J. Org. Chem. 1966, 31, 4263. Suga, K.; Watanabe, S.; Tsu, P. P. Aust. J. Chem. 1968, 21, 2341-2344. Carnahan, J. C.; Closson, W. D. J. Org. Chem. 1972, 37, 4469.
7. For review, see: Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972.
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9. (b) Naruse, Y.; Ito, Y.; Inagaki, S. J. Org. Chem. 1991, 56, 2256.
10. Preparation of starting 2,3-dialkylated indoles: Tietze, L. F.; Eicher, T. Reaktionen und Synthesen im organisch-chemischen Praktikum; Georg Thieme Verlag: Stuttgart, 1981. Japanese translation: Takano, S.; Ogasawara, K. Nankodo: Tokyo, 1983; pp 309-310, M-4a.
11. For the BuLi-t-BuOK complex base, see. Schlosser, M. J. Organomet. Chem. 1967, 8, 9. Schlosser, M. In Modern Synthetic Methods Vol. 6; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; pp 227-272; Schlosser, M. Organometallics in Synthesis; John Wiley and Sons: Chichester, 1994; pp 1-166.
12. For the BuLi-t-BuOK complex base, see. Schlosser, M. J. Organomet. Chem. 1967, 8, 9. Schlosser, M. In Modern Synthetic Methods Vol. 6; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; pp 227-272; Schlosser, M. Organometallics in Synthesis; John Wiley and Sons: Chichester, 1994; pp 1-166.
13. For the BuLi-t-BuOK complex base, see. Schlosser, M. J. Organomet. Chem. 1967, 8, 9. Schlosser, M. In Modern Synthetic Methods Vol. 6; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; pp 227-272; Schlosser, M. Organometallics in Synthesis; John Wiley and Sons: Chichester, 1994; pp 1-166.
14. Pausacker, K. H. J. Chem. Soc. 1950, 621. See also: Wakamatsu, T.; Hara, H.; Ban, Y. Heterocycles 1977, 8, 335.
15. Pausacker, K. H. J. Chem. Soc. 1950, 621. See also: Wakamatsu, T.; Hara, H.; Ban, Y. Heterocycles 1977, 8, 335.
16. + - Et), 168(31).
17. Maercker, A.; Troesch, J. J. Organomet. Chem. 1975, 102, C1. Maercker, A.; Passlack, M. Chem. Ber. 1982, 115, 540. Maercker, A.; Stoetzel, R. J. Organomet. Chem. 1983, 254, 1.
18. Maercker, A.; Troesch, J. J. Organomet. Chem. 1975, 102, C1. Maercker, A.; Passlack, M. Chem. Ber. 1982, 115, 540. Maercker, A.; Stoetzel, R. J. Organomet. Chem. 1983, 254, 1.
19. Maercker, A.; Troesch, J. J. Organomet. Chem. 1975, 102, C1. Maercker, A.; Passlack, M. Chem. Ber. 1982, 115, 540. Maercker, A.; Stoetzel, R. J. Organomet. Chem. 1983, 254, 1.
20. 2H with NOE enlargement by proton saturation. No significant change was observed in the aromatic region.
21. Inagaki, S.; Hirabayashi, Y. Chem. Lett. 1982, 709. Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724. Inagaki, S.; Iwase, K.; Goto, N. J. Org. Chem. 1986, 51, 362.
22. Inagaki, S.; Hirabayashi, Y. Chem. Lett. 1982, 709. Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724. Inagaki, S.; Iwase, K.; Goto, N. J. Org. Chem. 1986, 51, 362.
23. Inagaki, S.; Hirabayashi, Y. Chem. Lett. 1982, 709. Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724. Inagaki, S.; Iwase, K.; Goto, N. J. Org. Chem. 1986, 51, 362.
24. To avoid ethylation, the reaction mixture should be cooled immediately after generation of the dianion.