A simple catalyst-free, and highly regioselective approach to 2-hydroxyalkyl dithiocarbamates is described which involves a one-pot reaction of various amines and carbon disulfide,CS2, with epoxides in ethanol at room temperature.
Z. Cai, W. Zhou and L. Sun, “Synthesis and HMG CoA Reductase Inhibition of 4-Thiophenyl Quinolines as Potential Hypocholesterolemic Agents,” Bioorganic & Me- dicinal Chemistry, Vol. 15, No. 24, 2007, pp. 7809-7829. doi:10.1016/j.bmc.2007.08.044
J. Kendall, G. Rewcastle, R. Frederick, C. Mawson, W. Denny, E. Marshall, B. Baguley, C. Chaussade, S. Jackson and P. Shepherd, “Synthesis, Biological Evaluation and Molecular Modelling of Sulfonohy-drazides as Selective PI3K p110α Inhibitors,” Bioorganic & Medicinal Chemistry, Vol. 15, No. 24, 2007, pp. 7677-7687.
Y. Kanda, T. Ashizawa, K. Kawashima, S. Ikeda and T. Tamaoki, “Synthesis and Antitumor Activity of Novel C-8 Ester Derivatives of Leinamycin,” Bioorganic & Medicinal Chemistry Letters, Vol. 13, No. 13, 2003, pp. 455- 458.
A. Tyrkov, N. Urlyapova and A. Daudova, “Synthesis and Antimycobacterial Activity of Substituted 2-Nitro-1-(4-tol- fonyl)-2-(3-methylphenyl-1,2,4-oxadiazol-5-yl)Ethanes,” Pharmaceutical Chemistry Journal, Vol. 40, No. 7, 2006, pp. 377-379. doi:10.1007/s11094-006-0131-6
C. Jacob, “A Scent of Therapy: Pharmacological Implications of Natural Products Containing Redox-Active Sul- fur Atoms,” Natural Product Reports, Vol. 23, No. 6, 2006, pp. 851-863.
X. Y. Wang and Z. J. Guo, “The Role of Sulfur in Platinum Antican-cer Chemotherapy,” Anti-Cancer Agents in Medicinal Chemistry, Vol. 7, No. 1, 2007, pp. 19-34. doi:10.2174/187152007779314062
T. Ariga and T. Seki, “Antithrombotic and Anticancer Effects of Garlic-Derived Sul-fur Compounds: A Review,” BioFactors, Vol. 26, No. 2, 2006, pp. 93-103. doi:10.1002/biof.5520260201
A. van Zanten, M. Oudijk, M. Nohlmans-Paulssen, Y. van der Meer, A. Girbes and K. Polderman, “Continuous vs. Intermittent Cefotaxime Admini-stration in Patients with Chronic Obstructive Pulmonary Disease and Respiratory Tract Infections: Pharmacokinetics/ Pharmacody- namics, Bacterial Susceptibility and Clinical Efficacy,” British Journal of Clinical Pharmacology, Vol. 63, No. 1, 2007, pp. 100-109. doi:10.1111/j.1365-2125.2006.02730.x
E. D. Caldas, M. H. Conceic?o, M. C. C. Miranda, L. C. K. R. de Souza and J. F. Lima, “Determination of Dithiocarbamate Fungicide Residues in Food by a Spectropho- tometric Method Using a Vertical Disulfide Reaction System,” Journal of Agricultural and Food Chemistry, Vol. 49, No. 10, 2001, pp. 4521-4525. doi:10.1021/jf010124a
Y. Zhang and P. Talalay, “Anti-carcinogenic Activities of Organic Isothiocyanates—Chemistry and Mechanisms,” Cancer Research, Vol. 54, Suppl. 7, 1994, pp. S1976- S1981.
L. Ronconi, C. Marzano, P. Zanello, M. Corsini, G. Miolo, C. Macca, A. Trevisan and D. Fregona, “Gold(III) Dithiocarbamate Derivatives for the Treatment of Cancer: Solution Chemistry, DNA Binding, and Hemolytic,” Journal of Medicinal Chemistry, Vol. 49, No. 5, 2006, pp. 1648-1657. doi:10.1021/jm0509288
R. Bessho, K. Ma-tsubara and M. Kubota, “Pyrrolidine Dithiocarbamate, a Potent Inhibitor of Nuclear Factor Kappa-B (NF-Kappa-B) Activation, Prevents Apoptosis in Human Promyelocytic Leukemia HL-60 Cells and Thymocytes,” Biochemical Pharmacology, Vol. 48, No. 10, 1994, pp. 1883-1889. doi:10.1016/0006-2952(94)90586-X.
C. S. I. Nobel, M. Kimland and B. Lind, “Dithiocar- bamates Induce Apoptosis in Thymocytes by Raising the Intracellular Level of Redox-Active Copper,” Journal of Biological Chemistry, Vol. 270, No. 44, 1995, pp. 26202- 26208.
J. C. Tsai, M. Jain and C. M. Hsieh, “Induction of Apoptosis by Pyrrolidinedithiocarbamate and N-Acetylcy- steine in Vascular Smooth Musclecells,” Journal of Bio- logical Chemistry, Vol. 271, No. 7, 1996, pp. 3667-3670. doi:10.1074/jbc.271.7.3667
P. J. Nieu Wenhuizen, A. W. Ehlers, J. G. Haasnoot, S. R. Janse, J. Reedijk and E. J. Baerends, “The Mechanism of Zinc(II)-Dithiocarbamate-Accelerated Vulcanization Un- covered; Theoretical and Experimental Evidence,” Jour- nal of the American Chemical Society, Vol. 121, No. 1, 1999, pp. 163-168. doi:10.1021/ja982217n
M. R. Wood, D. J. Dun-calf, S. P. Rannard and S. Perrier, “Selective One-Pot Synthesis of Trithiocarbonates, Xan-thates, and Dithiocarbamates for use in RAFT/MADIX Living Radical Polymerizations,” Organic Letters, Vol. 8, No. 4, 2006, pp. 553-556. doi:10.1021/ol0525617
S. Z. Zard, “On the Trail of Xan-thates: Some New Chemistry from an Old Functional Group,” Angewandte Chemie International Edition in English, Vol. 36, No. 7, 1997, pp. 673-685. doi:10.1002/anie.199706721
D. H. R. Barton, “The Invention of Chemical Reactions- The Last Five Years,” Tetrahedron, Vol. 48, No. 13, 1992, pp. 2529-2544.
D. Zhang, J. Chen, Y. C. Liang and H. Zhou, “Facile Synthesis of Novel Ionic Liquids Containing Dithio-carbamate,” Synthetic Communications, Vol. 35, No. 4, 2005, pp. 521-526.
A. D. Dunn and W.-D. Rudorf, “Carbon Disulfide in Or- ganic Chemistry,” Ellis Horwood, Chichertes, 1989.
A. McClain and Y.-L. Hsieh, “Synthesis of Poly-styrene-Supported Dithiocarbamates and Their Complexation with Metal Ions,” Journal of Applied Polymer Science, Vol. 92, No. 1, 2004, pp. 218-225. doi:10.1002/app.13623
P. Morf, F. Raimondi, H.-G. Nothofer, B. Schnyder, A. Yasuda, J. M. Wessels and T. A. Jung, “Dithiocarbamates: Functional and Versatile Linkers for the Formation of Self-Assembled Monolayers,” Langmuir, Vol. 22, No. 2, 2006, pp. 658-663. doi:10.1021/la052952u
T. W. Greene and P. G. M. Wuts, “Protecting Groups in Organic Synthesis,” 3rd Edition, Wiley Interscience, New York, 1999.
T. R. Burke Jr., B. S. Bajwa, A. E. Jacobson, K. C. Rice, R. A. Streaty and W. A. Klee, “Probes for Narcotic Receptor Mediated Phenomena. 7. Synthesis and Pharma-cologi-cal Properties of Irreversible Ligands Specific for .Mu. or .Delta. Opiate Receptors,” Journal of Medicinal Chemistry, Vol. 27, No. 12, 1984, pp. 1570-1574. doi:10.1021/jm00378a008
W. Walter and K.-D. Bode, “Syntheses of Thiocar- bamates,” Angewandte Chemie Interna-tional Edition in English, Vol. 6, No. 4, 1967, pp. 281-293.
E. Lieber and R. O. Orlowski, “Hydrazinolysis of 1-(Al- kyldithioate)-Piperidine,” The Journal of Organic Chem- istry, Vol. 22, No. 1, 1957, pp. 88-92.
A. W. M. Lee, W. H. Chan, H. C. Wong and M. S. Wong, “One Pot Phase Transfer Synthesis of O-Alkyl, S-Methyl Dithiocarbonates (Xanthates),” Synthetic Communications, Vol. 19, No. 3-4, 1989, pp. 547-552.
R. N. Salvatore, S. Sahab and K. W. Jung, “Mild and Efficient Synthesis of Thiocarbonates and Thiocarbamates via a Three-Component Coupling Utilizing Cs2CO3 and TBAI,” Tetrahedron Letters, Vol. 42, No. 11, 2001, pp. 2055-2058.
N. Azizi, F. Aryanasab and M. R. Saidi, “Straightforward and Highly Efficient Catalyst-Free One-Pot Synthesis of Di-thiocarbamates under Solvent-Free Conditions,” Organic Letters, Vol. 8, No. 23, 2006, pp. 5275-5277. doi:10.1021/ol0620141
J. Tan, F. S. Liang, Y. M. Wang, X. Chang, Q. Liu and H. J. Yuan, “Carbon Tetrabro-mide-Mediated Carbon-Sulfur Bond Formation via a Sulfenyl Bromide Intermediate,” Organic Letters, Vol. 10, No. 12, 2008, pp. 2485-2488. doi:10.1021/ol800765s
S. Xia, X. Wang, Z.-M. Ge, T.-M. Cheng and R. T. Li, “An Efficient Synthesis of Aryldithiocar-bamic Acid Esters from Michael Addition of Electron-Deficient Alkenes with Arylamines and CS2 in Solid Media Alkaline Al2O3,” Tetrahedron, Vol. 65, No. 5, 2009, pp. 1005- 1009. doi:10.1016/j.tet.2008.11.084
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei and M. R. Saidi, “One-Pot Synthesis of Dithiocarbamates Accelerated in Water,” The Journal of Organic Chemistry, Vol. 71, No. 9, 2006, pp. 3634-3635. doi:10.1021/jo060048g
D. Chaturvedi and S. Ray, “An Efficient, One-Pot, Syn- thesis of Dithiocarbamates from the Corresponding Al- cohols using Mitsunobu’s Re-agent,” Tetrahedron Letters, Vol. 47, No. 20, 2006, pp. 1307-1309. doi:10.1016/j.tetlet.2005.12.079
T. Chung, H. Ishihara and S. A. Tejima, “A Facile Syn- thetic Approach for Alkyl α-Glycosides of Reducing Disaccharides,” Chemical & Pharmaceutical Bulletin, Vol. 26, No. 5, 1978, pp. 1570-1575.
S. Tsuboi, S. Takeda, Y. Yamasaki, T. Sakai, M. Utaka, S. Ishida, F. Yamada and J. Hirano, “A Convenient Synthesis of Platelet-Activating Factors and Their Analogs from Chiral Epichlor-ohydrine,” Chemistry Letters, Vol. 21, No. 8, 1992, pp. 1417-1420. doi:10.1246/cl.1992.1417
H. Natsugari, Y. Matsushita, N. Tamura, K. Yoshioko and M. Ochiai, “Synthesis of 5,6- cis-Carbapenems Related to C-19393 H2,” Journal of the Chemical Society, Perkin Transactions 1, 1983, pp. 403-411. doi:10.1039/p19830000403
I.-C. Chiu, US Pat. 5560853, 1996 (CAN 125: 333865).
L. Farng and A. G. Horodysky, US Pat. 5019284, 1991 (CAN 115: 236138).
E. Kato, JP 06019219, 1994 (CAN 121: 311855).
E. Kato, JP 04313763, 1992 (CAN 119: 213949).
J.-L. Cui, Z.-M. Ge, T.-M. Cheng and R. T. Li, “An Efficient One-Pot Synthesis of 2-Hydroxyalkyl Dithiocar- bamates,” Synthetic Communica-tions, Vol. 33, No. 12, 2003, pp. 1969-1976.
N. Azizi, B. Pourhasan, F. Aryanasab and M. R. Saidi, “A Simple and Novel Eco-Friendly Process for the One-Pot Synthesis of Di-thiocarbamates from Amines, Carbon Di- sulfide, and Epox-ides,” Synlett, No. 8, 2007, pp. 1239- 1242.
P. Werle, M. Trageser and S. Weiss, EP 386508, 1990 (CAN 114: 184824).
K. Itoh and K. Okonogi, EP 446877, 1991 (CAN 115: 280032).
R. A. Sheldon, “Green Solvents for Sustainable Organic Synthesis: State of the Art,” Green Chemistry, Vol. 7, No. 5, 2005, pp. 267-278. doi:10.1039/b418069k.
B. Movassagh and M. Soleiman-Beigi, “Stero- and Regioselective Thiolysis of 1,2-Epoxides in Water,” Synthetic Communications, Vol. 37, No. 18, 2007, pp. 3239- 3244. doi:10.1080/00397910701548100
B. Movassagh and A. Mossadegh, “Reductive Cleavage of S-S Bond by Zn/AlCl3 System: A Novel Method for the Synthesis of Sulfides from Alkyl Tosylates and Disulfides,” Synthetic Communications, Vol. 34, No. 9, 2004, pp. 1685-1690.
B. Movassagh and M. Shamsipoor, “Zinc-Mediated Cleav- age of Diselenides: A Novel Synthesis of Unsymmetrical Diorganyl Selenides in Aqueous Media,” Synlett, No. 1, 2005, pp. 121-122.
B. Movassagh and Y. Zakinezhad, “A New One-Pot Synthesis of Thiocar-bamates from Isocyanates and Disul- fides in the Presence of Zn/AlCl3 System,” Chemistry Letters, Vol. 34, No. 10, 2005, pp. 1330-1331. doi:10.1246/cl.2005.1330
B. Movassagh and Y. Zakinez-had, “Formation of Zinc Thiolates by Reductive Cleavage of Disulfides with the Zn/AlCl3 System in Aqueous Media, and Their Use for Michael Addition,” Zeitschrift für Naturfor-schung. B, A journal of chemical sciences, Vol. 61, No. 1, 2006, pp. 47-49.
B. Movassagh and M. Navidi, “One-Pot Synthesis of Beta-Hydroxysulfides from Styrenes and Disulfides Using the Zn/AlCl3 System,” Tetrahedron Letters. Vol. 49, No. 17, 2008, pp. 6712-6714. doi:10.1016/j.tetlet.2008.09.071
S. Balalaie, M. Barar-janian, A. M. Amani and B. Movassagh, “(S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetra-hydrobenzo[b]pyran Derivatives in Aqueous Media,” Synlett, No. 2, 2006, pp. 263-266. doi:10.1055/s-2006-926227
B. Movassagh and A. Tatar, “Zn/RuCl3-Promoted Cleavage of Diselenides: An Efficient Michael Addition of Zinc Selenolates to Conjugated Alkenes in Aqueous Media,” Synlett, Vol. 2007, No. 12, 2007, pp. 1954-1956. doi:10.1055/s-2007-984495
B. Movassagh and A. Fazeli, “Zinc-Mediated Cleavage of Diselenides: A Novel Synthesis of Selenoformates in Aque- ous Media,” Monatshefte für Chemie/Chemical Monthly, Vol. 138, No. 9, 2007, pp. 863-865. doi:10.1007/s00706-007-0642-1
B. Movassagh and M. Navidi, “Water Promoted Catalyst-Free Anti-Markovnikov Addition of Thiols to Styrenes,” Arkivok, 2008, pp. 47-53.
B. Movassagh and P. Shaygan, “Michael Addition of Thiols to α,β-Unsaturated Carbonyl Compounds Under Solvent-Free Conditions,” Arkivok, 2006, pp. 130-137.
B. Movassagh and M. Soleiman-Beigi, “Triethylamine- Catalyzed One-Pot Synthesis of Trithiocarbonates from Carbon Disulfide, Thiols, and Alkyl Halides in Water,” Monatshefte für Che-mie/Chemical Monthly, Vol. 139, No. 8, 2008, pp. 927-930. doi:10.1007/s00706-008-0864-x
B. Movassagh and M. Soleiman-Beigi, “Synthesis of Sulfides under Solvent- and Catalyst-Free Conditions,” Monatshefte für Chemie/Chemical Monthly, Vol. 140, No. 4, 2009, pp. 409-411. doi:10.1007/s00706-008-0043-0