SH-Methylation of SH-Containing Heterocycles with Dimethyl Carbonate via Phase-Transfer Catalytic Reaction

REFERENCES

• Shah , S. T. A. ; Khan , K. M. ; Martinez Heinrich , A. ; Voelter , W. An alternative approach towards the syntheses of thioethers and thioesters using CsF-celite in acetonitrile . Tetrahedron Lett. 2002 , 43 , 8281 – 8283 .
   Web of Science ®Google Scholar
• Narkhede , H. P. ; More , U. B. ; Dalal , D. S. ; Pawar , N. S. ; More , D. H. ; Mahulikar , P. P. Fly-ash-supported synthesis of 2-mercaptobenzothiazole derivatives under microwave irradiation . Synth. Commun. 2007 , 37 , 573 – 577 .
   Web of Science ®Google Scholar
• Mauleón , P. ; Alonso , I. ; Rodríguez Rivero , M. ; Carretero , J. C. Enantioselective synthesis of chiral sulfones by Rh-catalyzed asymmetric addition of boronic acids to α,β-unsaturated 2-pyridyl sulfones . J. Org. Chem. 2007 , 72 , 9924 – 9935 .
   PubMed Web of Science ®Google Scholar
• Hu , Y. ; Chen , Z. C. ; Le , Z. G. ; Zheng , Q. G. Organic reactions in ionic liquids: An efficient method for selective S-alkylation of 2-mercaptobenzothia(xa)zole with alkyl halides . Synth. Commun. 2004 , 34 , 2039 – 2046 .
   Web of Science ®Google Scholar
• Vlassa , M. ; Kezdi , M. ; Goia , I. Application of phase-transfer catalysis in the acridine series I:S-Alkylation and S-acylation of thioacridone and of some halogenated thioacridone derivatives . Synthesis 1980 , 10 , 850 – 851 .
   Google Scholar
• Heravi , M. M. ; Ahari , N. Z. ; Oskooie , H. A. ; Ghassemzadeh , M. Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1701–1712.
   Web of Science ®Google Scholar
• Shaikh , A. A. ; Sivaram , S. Organic carbonates . Chem. Rev. 1996 , 96 , 951 – 976 .
   PubMed Web of Science ®Google Scholar
• Ono , Y. Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block . Appl. Catal. A. 1997 , 155 , 133 – 166 .
   Web of Science ®Google Scholar
• Tundo , P. New developments in dimethyl carbonate chemistry . Pure Appl. Chem. 2001 , 73 , 1117 – 1124 .
   Web of Science ®Google Scholar
• Tundo , P. ; Selva , M. The chemistry of dimethyl carbonate . Acc. Chem. Res. 2002 , 35 , 706 – 716 .
   PubMed Web of Science ®Google Scholar
• (a) Janin , Y. L. ; Chiki , J. ; Legraverend , M. ; Huel , C. ; Bisagni , E. On the methylation of 3-cyano-6-hydroxypyridin-2(1H)-ones . Tetrahedron 1999 , 55 , 12797 – 12804 ; (b) Jyothi , T. M. ; Raja , T. ; Talawar , M. B. ; Rao , B. S. Selective O-methylation of catechol using dimethyl carbonate over calcined Mg-Al hydrotalcites . Appl. Catal. A. 2001 , 211 , 41 – 46 ; (c) Ouk , S. ; Thiébaud , S. ; Borredon , E. ; Legars , P. ; Lecomte , L. O-Methylation of phenolic compounds with dimethyl carbonate in solid/liquid phase transfer systems . Tetrahedron Lett. 2002 , 43 , 2661 – 2663 ; (d) Ouk , S. ; Thiébaud , S. ; Borredon , E. ; Legars , P. High-performance method for O-methylation of phenol with dimethyl carbonate . Appl. Catal. A. 2003 , 241 , 227 – 233 ; (e) Romero , M. D. ; Ovejero , G. ; Rodriguez , A. ; Gomez , J. M. ; Agueda , I. O-Methylation of phenol in liquid phase over basic zeolites . Ind. Eng. Chem. Res. 2004 , 43 , 8194 – 8199 ; (f) Shen , Z. L. ; Jiang , X. Z. ; Mo , W. M. ; Hu , B. X. ; Sun , N. Catalytic O-methylation of phenols with dimethyl carbonate to aryl methyl ethers using [BMIm]Cl . Green Chem. 2005 , 7 , 97 – 99 ; (g) Luque , R. ; Campelo , J. M. ; Conesa , T. D. ; Luna , D. ; Marinas , J. M. ; Romero , A. A. Catechol O-methylation with dimethyl carbonate over different acid–base catalysts . New J. Chem. 2006 , 30 , 1228 – 1234 ; (h) Wu , G. D. ; Wang , X. L. ; Chen , B. ; Li , J. P. ; Zhao , N. ; Wei , W. ; Sun , Y. H. Fluorine-modified mesoporous Mg-Al mixed oxides: Mild and stable base catalysts for O-methylation of phenol with dimethyl carbonate . Appl. Catal. A. 2007 , 329 , 106 – 111 .
   Web of Science ®Google Scholar
• (a) Jiang , X. L. ; Tiwari , A. ; Thompson , M. ; Chen , Z. H. ; Cleary , T. P. ; Lee , T. B. K. A practical method for N-methylation of indoles using dimethyl carbonate . Org. Proc. Res. Dev. 2001 , 5 , 604 – 608 ; (b) Shieh , W. C. ; Dell , S. ; Repič , O. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and microwave-accelerated green chemistry in methylation of phenols, indoles, and benzimidazoles with dimethyl carbonate . Org. Lett. 2001 , 3 , 4279 – 4281 ; (c) Selva , M. ; Tundo , P. ; Perosa , A. Reaction of functionalized anilines with dimethyl carbonate over NaY faujasite, 3: Chemoselectivity toward mono-N-methylation . J. Org. Chem. 2003 , 68 , 7374 – 7378 ; (d) Ouk , S. ; Thiébaud , S. ; Borredon , E. ; Chabaud , B. N-Methylation of nitrogen-containing heterocycles with dimethyl carbonate . Synth. Commun. 2005 , 35 , 3021 – 3026 ; (e) Selva , M. ; Perosa , A. Green chemistry metrics: A comparative evaluation of dimethyl carbonate, methyl iodide, dimethyl sulfate, and methanol as methylating agents . Green Chem. 2008 , 10 , 457 – 464 ; (f) Juárez , R. ; Padilla , A. ; Corma , A. ; García , H. Organocatalysts for the reaction of dimethyl carbonate with 2,4-diaminotoluene . Ind. Eng. Chem. Res. 2008 , 47 , 8043 – 8047 .
   Web of Science ®Google Scholar
• (a) Stanovnik , B. ; Tišler , M. ; Hribar , A. ; Barlin , G. B. ; Brown , D. J. Methylation of heterocyclic compounds containing imino, mercapto, and/or hydroxy groups by means of N,N-dimethylformamide dimethyl acetal. Aust. J. Chem. 1981, 34, 1729–1738; (b) Lissel , M. ; Schmidt , S. ; Neumann , B. Use of dimethyl carbonate as a methylating agent under phase-transfer-catalyzed conditions. Synthesis 1986, 382–383; (c) Tundo , P. ; Trotta , F. ; Moraglio , G. ; Ligorati , F. Continuous-flow processes under gas–liquid phase-transfer catalysis (GL-PTC) conditions: The reaction of dialkyl carbonates with phenols, alcohols, and mercaptans. Ind. Eng. Chem. Res. 1988, 27, 1565–1571; (d) Selva , M. ; Tundo , P. Highly chemoselective methylation and esterification reactions with dimethyl carbonate in the presence of NaY faujasite: The case of mercaptophenols, mercaptobenzoic acids, and carboxylic acids bearing OH substituents. J. Org. Chem. 2006, 71, 1464–1470.
   Web of Science ®Google Scholar
• Akiba , K. ; Shiraishi , H. ; Inamoto , N. Direct synthesis of 2,2-diaryl-3-methyl-2,3-dihydrobenzothiazoles from 3-methyl-2,3-dihydrobenzothiazole-2-thione and some mechanistic aspects . Bull. Chem. Soc. Jpn. 1979 , 52 , 156 – 159 .
   Web of Science ®Google Scholar
• Shridhar , D. R. ; Jogibhukta , M. ; Rao , P. S. ; Handa , V. K. An improved method for the synthesis of 2-thioxo-2,3-dihydro-1,3-benzoxazoles [2(3H)-benzoxazolethiones] . Synthesis. 1983 , 936 – 937 .
   Google Scholar
• Quast , H. ; Fuss , A. ; Nahr , U. Photochemical formation of methylenecyclopropane analogs, 11: Photochemical elimination of nitrogen from phenyl-substituted 1,4-dihydro-5-imino-5H-tetrazoles: Products of phenyl-substituted tris(imino)methane diradicals . Chem. Ber. 1985 , 118 , 2164 – 2185 .
   Google Scholar
• Tochtermann , W. ; Gustmann , H. ; Wolff , C. Carbon-13 NMR spectra of heterocycles, 1: Nitrogen heterocycles, 1: The reaction of bis(5-tetrazolyl) disulfides with diazoalkanes . Chem. Ber. 1978 , 111 , 566 – 573 .
   Google Scholar
• Harizi , A. ; Romdhane , A. ; Mighri , Z. Synthesis and reactivity of benzoxa(thia)zol-2-thiones: new route to 2-alkylthiobenzoxa(thia)zoles . Tetrahedron Lett. 2000 , 41 , 5833 – 5835 .
   Web of Science ®Google Scholar
• Berris , B. C. Recovery of quaternary ammonium salts from aqueous solution. U.S. Patent 5030757; Chem. Abstr. 1991 , 115 , 114015g .
   Google Scholar