Atypical oxidation reaction by thionyl chloride: Easy two-step synthesis of N-alkyl-1,4-dithiines

Synthetic Communications

Volumn 36, Issue 23, 2006, Pages 3591-3597

  Valla, Alain ^a,b   Cartier, Dominique ^a   Zentz, Frédéric ^a   Labia, Roger ^a  

^a CNRS   (France)

^b Chimie et Biologie des Substances Naturelles FRE 2125 CNRS 6   (France)

Author keywords

Dithiine; Imide; Isoimide; Thionyl chloride

Indexed keywords

BUTYRIC ACID; HETEROCYCLIC COMPOUND; IMIDE; INORGANIC COMPOUND; SUCCINIC ANHYDRIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; OXIDATION;

EID: 33845672563     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600943600     Document Type: Article

References (22)

1. Zentz, F.; Le Guillou, R.; Labia, R.; Sirot, D.; Linard, B.; Valla, A. Il Framaco 2004, 59, 879-886.
2. Zentz, F.; Hellio, C.; Valla, A.; De Labroise, D. Y.; Labia, R. Mar. Biotechnol. 2002, 4, 431-440.
3. Zentz, F.; Valla, A.; Le Guillou, R.; Labia, R.; Mathot, A.-G.; Sirot, D. Il Framaco 2002, 57, 421-426.
4. (a) Loudon, J. D.; Young, L. B.; Robertson, A. A. J. Chem. Soc. 1964, 591-593;
5. (b) Brisse, F.; Atfani, M.; Bergeron, J.-Y.; Belanger-Gariepy, F.; Armand, M. Acta Crystallogr., Sec. C 2000, C56, 190-192;
6. (c) Yamaguchi, Y.; Ueda, I. Acta Crystallogr., Sec. C 1984, C40, 113-115.
7. Moriarty, R. M.; Chien, C. C.; Jefford, C. W. Tetrahedron Lett. 1973, 4429-4431.
8. Buess, C. M.; Bradt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887-889.
9. Simmons, H. E.; Vest, R. D.; Blomstrom, D. C.; Roland, J. R.; Cairns, T. L. J. Am. Chem. Soc. 1962, 84, 4746-4756.
10. Ried, W.; Ochs, W. Chem. Ber. 1972, 105, 1093-1096.
11. Draber, W. Chem. Ber. 1967, 100, 1559-1570.
12. Krantz, A.; Lauren, J. J. Am. Chem. Soc. 1981, 103, 486-496.
13. Zilverschoon, A.; Meijer, J.; Vermeer, P.; Brandsma, L. Recl. Trav. Chim. Pays-Bas. 1974, 94, 163-165.
14. Meijer, J.; Vermeer, P.; Verkruijsse, H. D.; Brandsma, L. Recl. Trav. Chim. Pays-Bas. 1973, 92, 1326-1330.
15. Michaïlidis, A.; Giraud, M.; Molho, D. Organic Sulfur Chemistry; In Stirling, C. J. M., (Ed.); Butterworths: London, 1975; p. 466.
16. Hayakawa, K.; Mibu, N.; Osawa, E.; Kanematsu, K. J. Am. Chem. Soc. 1982, 104, 7136-7142.
17. Kim, J. H.; Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2001, 123, 87-95.
18. Draber, W.; Korte, F. U.S Patent 3364229, 1968.
19. Higa, T.; Krubsack, A. J. J. Org. Chem. 1975, 40, 3037-3045.
20. Pressman, D.; Bryden, J. H.; Pauling, L. J. Am. Chem. Soc. 1948, 70, 1352-1358.
21. Schreiber, K. C.; Fernandez, V. P. J. Org. Chem. 1961, 26, 1744-1747.
22. Zentz, F.; Labia, R.; Sirot, D.; Faure, O.; Grillot, R.; Valla, A. Il Farmaco 2005, 60, 944-947.