An efficient one-pot synthesis of 2-hydroxyalkyl dithiocarbamates

Synthetic Communications

Volumn 33, Issue 12, 2003, Pages 1969-1976

  Cui, Jia ling ^a   Ge, Ze mei ^a   Cheng, Tie ming ^a   Li, Runtao ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

2 Hydroxyalkyl dithiocarbamate; Anhydrous potassium phosphate; Carbon disulfide; Regioselective reaction; Ring opening of epoxide

Indexed keywords

ACETONE; AMINE; CARBON DISULFIDE; DITHIOCARBAMIC ACID DERIVATIVE; EPOXIDE; POTASSIUM DIHYDROGEN PHOSPHATE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038391329     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021023     Document Type: Article

References (24)

1. Gi, C.T.; Ishihara, H.; Tejima, S. A Facile synthetic approach for alkyl α-glycosides of reducing disaccharides. Chem. Pharm. Bull. 1978, 26 (5), 1570-1575.
2. Tsuboi, S.; Takeda, S.; Yamasaki, Y.; Sakai, T.; Utaka, M.; Ishida, S.; Yamada, E.; Hirano, J. A convenient synthesis of platelet-activating factors and their analogs from chiral epichlorohydrin. Chem. Lett. 1992, (8), 1417-1420.
3. Natsugari, H.; Matsushita, Y.; Tamura, N.; Yoshioko, K.; Ochiai, M. Synthesis of 5,6-cis-carbapenems related to C-19393 H2. J. Chem. Soc., Perkin Trans. 1 1983, (2), 403-411.
4. Itoh, K.; Okonogi, K. Preparation of Triazolylalkyl Dithiocarbamates as Fungicides. Eur. Patent 446,877, Sep 18, 1991 (CAN 115:280032).
5. (a) Werle, P.; Trageser, M.; Weiss, S. Preparation of Quaternary Ammonium Salts Containing Dithiocarbonate and Dithiocarbamate Residues as Bactericides and Fungicides. Eur. Patent 386,508, Sep 12, 1990 (CAN 114:184824);
6. (b) Werle, P.; Trageser, M.; Weiss, S. Liquid Industrial Microbicides Containing Quaternary Ammonium Salts and Another Microbicide. Eur. Patent 386,509, Sep 12, 1990 (CAN 114:180330).
7. Rafin, C.; Veignie, E.; Sancholle, M.; Postel, D.; Len, C.; Villa, P.; Ronco, G. Synthesis and antifungal activity of novel bisdithiocarbamate derivatives of carbohydrates against fusarium oxysporum f. sp. lini. J. Agric. Food Chem. 2000, 48 (11), 5283-5287.
8. (a) Len, C.; Postel, D.; Ronco, G.; Villa, P.; Goubert, C.; Jeufrault, E.; Mathon, B.; Simon, H. Synthesis of carbamic esters derivatives of itols: antifungal activity against various crop diseases. J. Agric. Food Chem. 1997, 45 (1), 3-6;
9. (b) Len, C.; Boulogne-Merlot, Anne-S.; Postel, D.; Ronco, G.; Villa, P.; Goubert, C.; Jeufrault, E.; Mathon, B.; Simon, H. Synthesis of antifungal activity of novel bis(dithiocarbamate) derivatives of glycerol. J. Agric. Food Chem. 1996, 44 (9), 2363-2365.
10. Gopalaswarmy, U.V.; Frei, E.; Frank, N.; Kliem, H.-C.; Wiessler, M.; Bertram, B.; Bhattacharya, R.K. Chemopreventive effects of dithiocarbamates on aflatoxin B1 metabolism and formation of AFB1 adducts with glutathion. Anticancer Res. 1998, 18 (3A), 1827-1832.
11. Lee, B.-H.; Bertram, B.; Schmezer, P.; Frank, N.; Wiessler, M. Sugar-linked dithiocarbamates as modulators of metabolic and genotoxic properties of N-nitroso compounds. J. Med. Chem. 1994, 37 (19), 3154-3162.
12. Postel, D.G.; Ronco, G.L.; Villa, P.J.; Ville, G.A.; Plan, R. Preparation of Glycerol Dithiocarbimates and Analogs as Antivirals. FR 2,638,457, May 04, 1990 (CAN 114:82424).
13. Chiu, I.-C. Dithiocarbamoyl Diols and Borate Esters thereof for Use in Lubricant Compositions. US Patent 5,560,853, Oct 01, 1996 (CAN 125:333865).
14. Farng, L.; Horodysky, A.G. Multifunctional Lubricant Additives. US Patent 5,019,284, May 28, 1991 (CAN 115:236138).
15. Kato, E. Electrophotographic Liquid Developer. JP 06,019,219, Jan 28, 1994 (CAN 121:311855).
16. Kato, E. Electrophotographic Liquid Developer. JP 04,313,763, Nov 05, 1992 (CAN 119:213949).
17. Stanior, U.; Wiessler, M. Reaction of aromatic epoxides with sodium dirthiocarbamate. Arch. Pharm. 1984, 317 (12), 1042-1047.
18. Yesilada, A.; Sarac, S.; Ertan, M.; Willke, A. Study on some new ornidazole derivatives. Hacettepe Univ. Eczacilik Fak. Derg. 1992, 12 (1), 13-21.
19. Trofimov, B.A.; Nedolya, N.A.; Komel'kova, V.I. Reaction of 1-(2-vinyloxyethoxy)-2,3-epoxypropane with dithiocarbamic acid synthesie of new dithiocarbamates. Z. Chem. 1987, 27 (1), 24-25.
20. (a) Li, R.T.; Ding, P.Y.; Han, M.; Cai, M.S. A simple one-pot preparation of dithiocarbamates in the presence of anhydrous potassium phosphate. Synth. Commun. 1998, 28 (2), 295-300;
21. (b) Li, R.T.; Cai, M.S. Convenient synthesis of 1,4-di(alkyldithioate) piperazines. Synth. Commun. 1999, 29 (1), 65-71;
22. (c) Ge, Z.M.; Li, R.T.; Cheng, T.M. An efficient synthesis of formylmethyl piperidine 1-carbodithioate diethyl acetal and its analogs. Synth. Commun. 1999, 29 (18), 3191-3196;
23. (d) Li, R.T.; Ge, Z.M.; Cheng, T.M.; Cai, M.S. New synthesis method for dithiocarbamates. Chem. J. Chin. Univ. 1999, 20 (12), 1897-1902.
24. Lieber, E.; Orlowski, R.C. Hydrazinolysis of 1-(alkyldithioate)-piperidine. J. Org. Chem. 1957, 22 (1), 88-89.