SH-methylation of SH-containing heterocycles with dimethyl carbonate via phase-transfer catalytic reaction

Synthetic Communications

Volumn 41, Issue 6, 2011, Pages 871-878

  Xie, Jian Gang ^a,b   Quan, Jing ^a   Li, Shu Bai ^a   Zheng, Yan ^a   Zhu, Li Min ^a  

^a DONGHUA UNIVERSITY   (China)

^b ZHENGZHOU NORMAL UNIVERSITY   (China)

Author keywords

Dimethyl carbonate; methylation; phase transfer catalyst; SH containing heterocycle; thioether

Indexed keywords

CARBONIC ACID; DIMETHYL SULFATE; HALIDE; HETEROCYCLIC COMPOUND; POTASSIUM CARBONATE; SULFIDE; TETRABUTYLAMMONIUM; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; MASS SPECTROMETRY; MELTING POINT; METHYLATION; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS;

EID: 79952074614     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003707048     Document Type: Article

References (34)

1. 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. (Pubitemid 35223356)
2. 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.
3. Mauleó n, P.; Alonso, I.; Rodríguez Rivero, M.; Carretero, J. C. Enantioselective synthesis of chiral sulfones by Rh-catalyzed asymmetric addition of boronic acids to a,b-unsaturated 2-pyridyl sulfones. J. Org. Chem. 2007, 72, 9924-9935.
4. 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. (Pubitemid 38780514)
5. 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.
6. 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. (Pubitemid 41512251)
7. Shaikh, A. A.; Sivaram, S. Organic carbonates. Chem. Rev. 1996, 96, 951-976. (Pubitemid 126641474)
8. Ono, Y. Catalysis in the production and reactions of dimethyl carbonate, an environmentally benign building block. Appl. Catal. A. 1997, 155, 133-166. (Pubitemid 127398691)
9. Tundo, P. New developments in dimethyl carbonate chemistry. Pure Appl. Chem. 2001, 73, 1117-1124.
10. Tundo, P.; Selva, M. The chemistry of dimethyl carbonate. Acc. Chem. Res. 2002, 35, 706-716.
11. (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;
12. (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; (Pubitemid 32264301)
13. (c) Ouk, S.; Thié baud, 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; (Pubitemid 34242753)
14. (d) Ouk, S.; Thié baud, S.; Borredon, E.; Legars, P. High-performance method for O-methylation of phenol with dimethyl carbonate. Appl. Catal. A. 2003, 241, 227-233;
15. (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;
16. (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; (Pubitemid 40311511)
17. (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; (Pubitemid 44174323)
18. (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. (Pubitemid 47239407)
19. (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; (Pubitemid 33586292)
20. (b) Shieh, W. C.; Dell, S.; Repic, 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; (Pubitemid 33627265)
21. (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; (Pubitemid 37122488)
22. (d) Ouk, S.; Thié baud, S.; Borredon, E.; Chabaud, B. N-Methylation of nitrogen-containing heterocycles with dimethyl carbonate. Synth. Commun. 2005, 35, 3021-3026; (Pubitemid 41722049)
23. (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; (Pubitemid 351466554)
24. (f) Juá rez, R.; Padilla, A.; Corma, A.; Garcí a, H. Organocatalysts for the reaction of dimethyl carbonate with 2,4-diaminotoluene. Ind. Eng. Chem. Res. 2008, 47, 8043-8047.
25. (a) Stanovnik, B.; Tisler, 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;
26. (b) Lissel, M.; Schmidt, S.; Neumann, B. Use of dimethyl carbonate as a methylating agent under phase-transfer-catalyzed conditions. Synthesis 1986, 382-383;
27. (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;
28. (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.
29. 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.
30. 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.
31. 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.
32. 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.
33. 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. (Pubitemid 30490632)
34. Berris, B. C. Recovery of quaternary ammonium salts from aqueous solution. U.S. Patent 5030757; Chem. Abstr. 1991, 115, 114015g.