Methods for Converting N-Alkyl Lactams to Vinylogous Urethanes and Vinylogous Amides via (Methylthio)alkylideniminium Salts

Journal of Organic Chemistry

Volumn 46, Issue 18, 1981, Pages 3671-3675

  Gugelchuk, Mary M ^a   Hart, David J ^a   Tsai, Yeun Min ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001213432     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00331a018     Document Type: Article

References (31)

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2. For the first application of the “sulfide-contraction” procedure to N-alkyl lactams see: Yamaguchi, H. Chem. Abstr. 1973, 78, 29617
3. For other applications of the “sulfide-contraction” procedure to N,N-dialkyl amides and N-alkyl lactams see: Gerrans, G. C.; Howard, A. S.; Orlek, B. S. Tetrahedron Lett. 1975, 4171. Ireland, R. E.; Brown, F. R., Jr. J. Org. Chem. 1980, 45, 1868.
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10. For a relevant review see: Brinkmeyer, R. S.; Abdulla, R. F. Tetrahedron 1979, 35, 1675.
11. For a related reaction see: Howe, R. K. J. Org. Chem. 1969,34,230.
12. Bredereck, H.; Bredereck, K. Chem. Ber. 1961, 94, 2278.
13. To our knowledge, the only reported intermolecular reactions between enolizable (alkylthio)alkylideniminium salts and active methylene compounds were reported in a Japanese patent: Yamaguchi, H. Chem. Abstr. 1965, 63, 1832 1.
14. For other reactions between nonenolizable (alkylthio)alkylideniminium salts and active methylene compounds see: Restle, S.; Wermuth, C. G. Tetrahedron Lett. 1979, 4837.
15. For a method of converting IV-alkyl lactams to vinylogous ureas, see: Rathke, M. W.; Woodbury, R. P. Tetrahedron Lett. 1978,709. This method gave only trace amounts of vinylogous urea with lactam i.
16. For other uses of (alkylthio)alkylideniminium salts, see: Harada, T.; Tamuro, Y.; Yoshida, Z. Chem. Lett. 1979,1353. Raucher, S.; Klein, P. Tetrahedron Lett. 1980, 4061.
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19. White, D. A. Synth. Commun. 1977, 7, 559.
20. One might have anticipated competition between ketene S,Nacetal formation13 and iminium ion addition under the basic conditions used throughout this study.
21. Howard, A. S.; Gerrans, G. C.; Michael, J. P. J. Org. Chem. 1980, 45,1713. Yamada, Y.; Miljkovic, D.; Wehrli, P.; Gelding, B.; Löliger, P.; Keese, R.; Müller, K.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1969, 8, 343.
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23. For a related reaction, see: Wenkert, E. Acc. Chem. Res. 1968, 1, 78.
24. For a hydrogenolysis-decarboxylation procedure which may be suitable for converting compounds of type 7 to vinylogous amides, see: Horii, Z.; Morikawa, K.; Ninomiya, I. Chem. Pharm. Bull. 1969,17, 2230.
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28. Purchased from Fisher.
29. Purchased from Aldrich Chemical Co.
30. Purchased from Eastman Chemical Co.
31. Strube, R. E. “Organic Syntheses”; Wiley: New York, 1963; Collect. Vol. TV, p 417.