One‐Pot Direct Synthesis of Thiocarbamates from Aniline, Carbon Monoxide, and Thiols Catalyzed by Selenium

References

• Goel , A. , Mazur , S. J. , Fattah , R. J. , Hartman , T. L. , Turpin , J. A. , Huang , M. , Rice , W. G. , Appella , E. and Inman , J. K. 2002 . Benzamide‐based thiolcarbamates: A new class of HIV‐1 NCp7 inhibitors . Bioorg. Med. Chem. Lett. , 12 : 767
   PubMed Web of Science ®Google Scholar
• Xue , M. , Long , B. , Fairchild , H. C. , Johnston , K. , Rose , W. C. , Kadow , J. F. , Vyas , D. M. and Chen , S. H. 2000 . Structure‐activity relationships study at the 3′‐N position of paclitaxel. Part 2: synthesis and biological evaluation of 3′‐N‐thiourea‐ and 3′‐N‐thiocarbamate‐bearing paclitaxel analogues . Bioorg. Med. Chem. Lett. , 10 : 1327
   PubMed Web of Science ®Google Scholar
• Harwood , J. L. 1994 . Thiocarbamates and surface lipid synthesis . Biochem. Soc. Trans. , 22 : 621
   PubMedGoogle Scholar
• Rodis , N. P. and Digenis , G. A. 2001 . Synthesis and in‐vitro evaluation of novel low molecular weight thiocarbamates as inhibitors of human leukocyte elastase . J. Enzyme Inhib. , 16 : 95
   Web of Science ®Google Scholar
• Worthing , C. R. 1991 . The Pesticide Mannal , 9th ed Edited by: Worthing , C. R. London : British Crop Protection Council .
   Google Scholar
• Breiter , W. A. , Baker , J. M. and Koskinen , W. C. 1998 . Direct measurement of Henry's constant for s‐ethyl N,N‐Di‐n‐propylthiocarbamate . J. Agric. Food Chem. , 46 : 1624
   Google Scholar
• Lee , S. J. , Caboni , P. , Tomizawa , M. and Casida , J. E. 2004 . Cartap hydrolysis relative to its action at the insect nicotinic channel . J. Agric. Food Chem. , 52 : 95
   Google Scholar
• Chen , Y. S. , Schuphan , I. and Casida , J. E. 1979 . S‐chloroallyl thiocabamate herbicides: mouse hepatic microsomal oxygenase and rat metabolism of cis‐ and trans‐[14C˭O]diallate . J. Agric. Food Chem. , 27 : 709
   PubMed Web of Science ®Google Scholar
• Sanders , H. J. 1981 . Herbicides . Chem. Eng. News , 59 : 20
   Google Scholar
• Mizuno , T. , Nishiguchi , I. , Okushi , T. and Hirashima , T. 1991 . Facile synthesis of s‐alkyl thiocarbamates through reaction of carbamoyl lithium with elemental sulfur . Tetrahedron Lett. , 32 : 6867
   Web of Science ®Google Scholar
• Nagao , Y. , Abe , Y. , Misono , T. , Ichizen , N. , Shima , Y. , Iesaka , H. and Furushima , M. 1993 . Synthesis and biological activities of phenylcarbamates and phenylthiocarbamates . Nippon Kagaku Kaishi , : 719
   Google Scholar
• Sonoda , N. , Mizuno , T. , Murakami , S. , Konda , K. , Ogawa , A. and Ryu , I. 1989 . Selenium‐catalyzed synthesis of s‐alkyl thiocarbamates from amines, carbon monoxide, sulfur, and alkyl halides . Angew. Chem. Int. Ed. Engl. , 28 : 452
   Google Scholar
• Mizuno , T. , Nishiguchi , I. and Sonoda , N. 1994 . Novel synthesis of s‐alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst . Tetrahedron , 50 : 5669
   Google Scholar
• Mizuno , T. , Daigaku , T. and Nishiguchi , I. 1965 . Reaction of thiolates with carbon monoxide . Tetrahedron Lett. , 36 : 1533
   Google Scholar
• Mizuno , T. , Junko , T. and Ogawa , A. 2003 . Facile s‐alkyl thiocarbamates synthesis by a novel DBU‐assisted carbonylation of amines with carbon momoxide and sulfer . Tetrahedron , 59 : 1327
   Google Scholar
• Mizuno , T. , Iwai , T. , Ogawa , A. and Ito , T. 2004 . Practical synthesis of s‐alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfer . Tetrahedron , 60 : 2869
   Google Scholar
• Kwart , H. and Evans , E. R. 1966 . The vapor phase rearrangement of thioncarbonates and thioncarbamates . J. Org. Chem. , 31 : 410
   Web of Science ®Google Scholar
• Hackler , R. E. and Balko , T. W. 1973 . The [3, 3]‐sigmatropic rearrangement of allylic dialkylthiocarbamates . J. Org. Chem. , 38 : 2106
   PubMedGoogle Scholar
• Sakamoto , M. , Yoshiaki , M. , Takahashi , M. , Fujita , T. and Watanabe , S. 1995 . Photochemical isomerization of o‐allyl and o‐but‐3‐enyl thiocarbamates . J. Chem. Soc. Perkin Trans. 1 , : 373
   Google Scholar
• Bohme , A. and Gais , H. J. 1999 . Palladium catalyzed enantioseletive rearrangement of o‐allylic thiocarbamates: Asymmetric synthesis of allylic thiols . Tetrahedron: Asymmetry , 10 : 2511
   Google Scholar
• Overberger , C. G. , Ringsdorf , H. and Weinshenker , N. 1962 . Preparation and polymerization of S‐, O‐, and N‐vinyl derivatives of carbonic acid.1 unsaturated carbonic acid derivatives . J. Org. Chem. , 27 : 4331
   Google Scholar
• Ricci , A. , Danieli , R. and Pirazzini , G. 1977 . Addition reactions of benzenethiol to unsaturated systems catalyzed by trimethyl(phenylthio)‐silane or ‐stannane . J. Chem. Soc. Perkin Trans. 1 , : 1069
   Google Scholar
• Marr , F. and Hoppe , D. 2002 . Synthesis of enantiomerically enriched tertiary 2‐cyclohexene‐1‐thiols via configurationally stable‐thio‐substituted allyllithium compounds . Org. Lett. , 4 : 4217
   Google Scholar
• Grzyb , J. A. , Shen , M. , Ishii , C. Y. , Chi , W. , Brown , R. S. and Batey , R. A. 2005 . Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides . Tetrahedron , 61 : 7153
   Web of Science ®Google Scholar
• Jones , W. D. , Reynolds , K. A. , Sperry , C. K. , Lachicotte , R. J. , Godleski , S. A. and Valente , R. R. 2000 . Selective carbonylation routes to thiocarbamates. An alternative to phosgene . Organometallics , 19 : 1661
   Google Scholar
• Jacob , J. , Reynolds , K. A. , Jones , W. D. , Godleski , S. A. and Valente , R. R. 2001 . Nickel‐mediated selective carbonyltion routes to thiocarbamates . Organometallics , 20 : 1028
   Google Scholar
• Koch , P. 1975 . Selenium catalyzed carbonylation of amine and disulfieds. A new synthesis of thiocarbamates . Tetrahedron Lett. , 25 : 2087
   Google Scholar
• Wynne , J. H. , Jensen , S. D. and Snow , A. W. 2003 . Facile one‐pot synthesis of s‐alkyl thiocarbamates . J. Org. Chem. , 68 : 3733
   Google Scholar
• Sonoda , N. , Yamamoto , G. , Natsukawa , K. , Kondo , K. and Murai , S. 1975 . A new synthesis of heterocycles by the reaction of amino and alcohol or amino thiols with carbon monoxide in the presence of selenium . Tetrahedron Lett. , 24 : 1969
   Google Scholar
• Zhang , X. P. and Lu , S. W. 2005 . A new and facile route for the synthesis of thiocarbamates from aniline, carbon monoxide, and thiols mediated by selenium . Chem. Lett. , 34 : 606
   Web of Science ®Google Scholar
• Mei , J. T. and Lu , S. W. 2002 . Reaction process phase transfer catalysis for selective oxidative‐reductive carbonylation to monuron . Chin. J. Catal. , 23 : 1
   Google Scholar
• Mei , J. T. , Yang , Y. , Xue , Y. and Lu , S. W. 2003 . Selective formation of unsymmetric ureas by selenium‐catalyzed oxidative‐reductive carbonylation with CO . J. Mol. Catal. A: Chem. , 191 : 135
   Google Scholar
• Sonoda , N. , Yasuhara , T. , Kondo , K. , Ikeda , T. and Tsutsumi , S. 1971 . A new synthesis of urea. The reaction of ammonia or aliphatic amines with carbon monoxide in the presence of selenium . J. Am. Chem. Soc. , 93 : 6344
   Google Scholar
• Ogawa , A. , Kambe , N. , Murai , S. and Sonoda , N. 1985 . Selenium‐assisted carbonylation of alkyl ketones with carbon monoxide . Tetrahedron , 41 : 4813
   Google Scholar
• Birch , R. S. , Gowan , W. S. and Norris , P. 1925 . Some reactions of substituted mercaptomagnesium halides . J. Chem. Soc. , 127 : 904
   Google Scholar
• Yoshida , K. , Isobe , M. , Yano , K. and Nagamatsu , K. 1985 . N‐nitroso compounds. IV. Reaction of N‐nitrosourea with thiol. A new synthesis of thiocarbamic S‐esters . Bull. Chem. Soc. Jpn. , 58 : 2143
   Google Scholar
• Baskakow , C. 1966 . J. Org. Chem. USSR (Engl. Transl.) , 2 : 1191
   Google Scholar
• Werner , E. A. 1890 . Interaction of benzyl chloride and ally1 bromide, respectively, with thiocarbamide, monophenylthiocarbamide and diphenylthiocarbamide . J. Chem. Soc. , 57 : 303
   Google Scholar
• Bourne , N. , Williams , A. , Douglas , K. I. and Penkava , T. R. 1984 . The E1CB mechanism for thiocarbamate ester hydrolysis: equilibrium and kinetic studies . J. Chem. Soc. Perkin Trans. 2 , : 1827
   Google Scholar
• McKinley , N. S. 1944 . Phenyl isocyanate derivatives of certain alkylated phenols. Melting points and x‐ray powder diffraction data . Ind. Eng. Chem. Anal. Ed. , 16 : 304
   Google Scholar
• Satchell , D. P. N. , Satche:ll , R. S. and Wassef , W. N. 1992 . Kinetics of the mercury(II) ion‐promoted desulfurisation of thiocarbamates in auqeous solution . J. Chem. Soc. Perkin Trans. 2 , : 1199
   Google Scholar