Synthesis of aromatic thioamide from nitrile without handling of gaseous hydrogen sulfide

Synthetic Communications

Volumn 35, Issue 5, 2005, Pages 761-764

  Manaka, Akira ^a   Sato, Masakazu ^a  

^a TAISHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Magnesium chloride; Nitriles; Thioamides

Indexed keywords

AROMATIC COMPOUND; HYDROGEN SULFIDE; MAGNESIUM CHLORIDE; N,N DIMETHYLFORMAMIDE; NITRILE; SODIUM HYDROGEN SULFIDE; THIOAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS; MATERIALS HANDLING; REACTION ANALYSIS; REPRODUCIBILITY; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE;

EID: 15244344350     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200050393     Document Type: Article

References (19)

1. Klimesová, V.; Svoboda, M.; Karel Waisser, K.; Kaustová, J.; Buchta, V.; Králová, K. Eur. J. Med. Chem. 1999, 34 (5), 433-440 and references cited therein.
2. Bahadir, M.; Nitz, S.; Parlar, H.; Korte, F. J. Agric. Food Chem. 1979, 27 (4), 815-818.
3. (a) Brown, K.; Cater, D. P.; Cavalla, J. F.; Green, D.; Newberry, R. A.; Wilson, A. B. J. Med. Chem. 1974, 17 (11), 1177-1181;
4. (b) Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20 (2), 256-262.
5. Wagner, G.; Voigt, B.; Vieweg, H. Pharmazie 1984, 39, 226-230.
6. For reviews, see: (a) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5 (5), 447-461;
7. (b) Kurd, R. N.; DeLaMater, G. Chem. Rev. 1961, 61 (1), 45-86.
8. Kindler, K.; Burghard, F. Liebigs Ann. Chem. 1923, 431, 201.
9. Fairfull, A. E.S.; Lowe, J. L.; Peak, D. A. J. Chem. Soc. 1952, 742-744.
10. Cassar, L.; Panossian, S.; Giordano, C. Synthesis 1978, 917-919.
11. Liboska, R.; Zyka, D.; Bobek, M. Synthesis 2002, 1649-1651.
12. Cashman, J. R. J. Org. Chem. 1982, 47 (24), 4645-4650.
13. Benner, S. A. Tetrahedron Lett. 1981, 22 (20), 1851-1854.
14. Sakai, T. T.; Krishna, N. R. Bioorg. Med. Chem. 1999, 7 (8), 1559-1565.
15. Okamiya, J. Nippon Kagaku Zasshi 1965, 86 (3), 315-319; Chem. Abstr. 1965, 63, 23553.
16. Okamiya, J. Nippon Kagaku Zasshi 1965, 86 (3), 315-319; Chem. Abstr. 1965, 63, 23553.
17. Bjorklund, M. D.; Coburn, M. D. J. Heterocycl. Chem. 1980, 17 (4), 819-821.
18. Papadopoulos, E. P. J. Org. Chem. 1974, 39 (17), 2540-2542.
19. 2S gas in triethylamine and pyridine, See: Sato, M.; Manaka, A.; Takahashi, K.; Kawashima, Y.; Hatayama, K. PCT Pat. Appl. WO 9402472; Chem. Abstr. 1995, 122, 10024.