Conversion of 2-methylthio-4-trifluoroacetyl-5,6-dihydro-4H-1,3,4-thiadiazines intoα,β-unsaturated esters via carbanion-induced ring opening and desulfurization

Chemistry Letters

Volumn , Issue 4, 1998, Pages 329-330

  Shimada, Kazuaki ^a   Otaki, Akihiro ^a   Yanakawa, Masaki ^a   Mabuchi, Shosuke ^a   Yamakado, Naoya ^a   Shimoguchi, Takeshi ^a   Takikawa, Yuji ^a  

^a IWATE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005577958     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.329     Document Type: Article

References (10)

1. a) K. Shimada, A. Otaki, M. Yanakawa, S. Mahuchi, N. Yamakado, T. Shimoguchi, K. Inoue, T. Kagawa, K. Shoji, and Y. Takikawa, Chem. Lett., 1995, 925.
2. b) K. Shimada, A. Otaki, M. Yanakawa, S. Mabuchi, N. Yamakado, T. Shimoguchi, K. Inoue, T. Kagawa, K. Shoji, and Y. Takikawa, Bull. Chem. Soc. Jpn., 69, 1043 (1996), and the references cited therein.
3. a) F. Babudri, S. Florio, G. Indelicati, and G. Trapani, J. Org. Chem., 48, 4082 (1983).
4. b) F. Babudri, S. Florio, A. Reho, and G. Trapani, J. Chem. Soc., Perkin Trans I, 1984, 1949.
5. M. Busch and M. Starke, J. Prakt. Chem., 93, 59 (1916).
6. The physical data of 2, 3, and 6 are available as supplementary materials.
7. 1H NMR spectrum of major-3a comparing with that of minor-3a (δ=7.0-7.5 ppm).
8. H. Wislicenum and L. Kaufmann, Ber., 28, 1323 (1895).
9. 1H NMR spectra are J=15.0 -16.0 Hz, respectively.
10. 1H NMR spectrum of the mixture of 6a.