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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
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Original Articles

Organic Reactions in Ionic Liquids: An Efficient Method for Selective S‐Alkylation of 2‐Mercaptobenzothia(xa)zole with Alkyl Halides

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Pages 2039-2046 | Received 28 Oct 2003, Published online: 20 Aug 2006

References

  • Harizi , A. , Romdhane , A. and Mighri , Z. 2000 . Synthesis and reactivity of benzoxa(thia)zol‐2‐thiones: new route to 2‐alkylthiobenzoxa(thia)zoles . Tetrahedron Lett. , 41 ( 31 ) : 5833 – 5835 .
  • Husain , M. I. and Kumar , V. 1992 . Synthesis and studies of 3‐[(2‐benzothiazoly/benzimidazolyl/benzoxazolylthio)methyl]‐1,2,4‐triazolo[3,4,b] [1,3,4]thiadiazol‐6‐yl substituted phenyl as possible anthelmintics . Ind. J. Chem. Sect. B. , 31B ( 10 ) : 673 – 676 .
  • El‐Shaaer , H. M. , Abdel‐Aziz , S. A. , Allimony , H. A. , Ali , U. F. and Abdel‐Rahman , R. M. 1997 . Synthesis and antimicrobial activities of some new 2‐substituted benzoxazole/benzothiazole derivatives . Pharmazie , 52 ( 8 ) : 585 – 589 .
  • Johnson , C. A. , Mahamoud , A. , Brouant , P. , Galy , A. M. , Galy , J. P. , Barbe , J. , Concha , M. V. , Juan , C. C. and Osuna , A. 1992 . Synthesis of some new lead trypanocidal compounds belonging to the mercaptobenzazole series . Med. Chem. Res. , 2 ( 4 ) : 247 – 255 .
  • Maier , G. S. and Dobias , B. 1997 . 2‐mercaptobenzothiazole and derivatives in the flotation of galena, chalcocite and sphalerite: a study of flotation, adsorption and microcalorimetry . Miner. Eng. , 10 ( 12 ) : 1375 – 1393 . [CROSSREF]
  • Zhang , J. , Zhang , Z. , Liu , W. and Xue , Q. 1998 . The tribological behaviors of 2‐mercaptobenzoxazole derivatives as additives in liquid paraffin . Wear , 219 ( 2 ) : 184 – 187 . [CROSSREF]
  • Zhong , B. , Fan , Z. J. and Li , Z. M. 2003 . Synthesis and biological activity of 2‐substituted benzoxazole derivatives . Chin. J. Appl. Chem. , 20 ( 7 ) : 684 – 686 .
  • Paramashivappa , R. , Phani Kumar , P. , Subba Rao , P. V. and Srinivasa Rao , A. 2003 . Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors . Bioorg. Med. Chem. Lett. , 13 ( 4 ) : 657 – 660 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Herdan , J. , Crisan , L. , Baliu , S. , Luca , M. and Iordanche , G. Preparation of 2‐mercaptobenzazole derivatives with potential biological activities . Rom. RO 90 . 30 October, 1986 . 456
  • Antonova , A. and Kalcheva , V. 1989 . Synthesis of 2‐[(2‐substituted iminoalkyl)thio]benzothiazoles . Izv. Khim. , 22 ( 1 ) : 158 – 163 .
  • Kalcheva , V. and Tosheva , M. 1991 . Alkylation of 2(3)‐benzoxazolethiones with α‐haloketones and methyl vinyl ketone . Izv. Khim. , 24 ( 3 ) : 394 – 399 .
  • Sidoova , E. , Danek , J. and Konecny , V. 2‐[[[(2‐Ethyl‐6‐methylphenyl)carbamonyl]methyl]thio]benzothiazole with anthelmintic activity and its preparation . Czech. CS 276 . 13 May, 1992 . 388
  • Sih , J. C. and Graber , D. R. 1983 . 2‐Mercapto‐1,3‐benzoxazole: a useful reagent for the preparation of symmetrical and unsymmetrical sulfides . J. Org. Chem. , 48 ( 21 ) : 3842 – 3845 .
  • Liunova , L. M. and Rozhkova , N. K. 1969 . Reaction of 2‐mercaptobenzothiazole with alkyl halides . Uzb. Khim. Zh. , 13 ( 6 ) : 24 – 26 .
  • Ono , N. , Miyake , H. , Saito , T. and Kaji , A. 1980 . A convenient synthesis of sulfides, formaldehyde dithioacetals and chloromethyl sulfides . Synthesis , : 952 – 953 . [CROSSREF]
  • Khurana , J. M. and Sahoo , P. K. 1992 . Chemoselective alkylation of thiols: a detailed investigation of reaction of thiols with halides . Synth. Commun. , 22 ( 12 ) : 1691 – 1702 .
  • Giri , S. and Mishra , A. K. 1984 . Synthesis of some benzoxazol‐2‐yl alkyl/arylalkyl sulfides and sulfones as potential pesticides . Curr. Sci. , 53 ( 6 ) : 301 – 303 .
  • Rani , B. R. , Bhalerao , U. T. and Rahman , M. F. 1990 . An unusual S‐ and N‐alkylation of mercaptosubstituted hetercycles with O,O‐dialkylchlorophosphate/thiophosphate . Synth. Commun. , 20 ( 19 ) : 3045 – 3052 .
  • Goralski , C. T. and Burk , G. A. 1977 . A convenient synthesis of (chloromethyl)thio aromatics and (chloromethyl)thio heteroaromatics . J. Org. Chem. , 42 ( 18 ) : 3094 – 3096 .
  • Henri , J. M. , Hassanaly , P. , Kister , J. and Metzger , J. 1977 . Selective S‐alkylation in phase transfer catalysis of 2‐pyridine‐, ‐pyrimidine‐ and benzoxazolethione . Phosphorous Sulfur , 3 ( 3 ) : 355 – 358 .
  • Shah , S. T.A. , Khan , K. M. , Angelica , M. H. and Voelter , W. 2002 . An alternative approach towards the synthesis of thioethers and thioesters using CsF‐Celite in acetonitrile . Tetrahedron Lett. , 43 ( 46 ) : 8281 – 8283 . [CROSSREF]
  • Welton , T. 1999 . Room temperature ionic liquids. Solvent for synthesis and catalysis . Chem. Rev. , 99 ( 8 ) : 2071 – 2083 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Wasserscheid , P. and Keim , W. 2000 . Ionic liquids‐new solutions for transition metal catalysis . Angew. Chem. Int. Edit. , 39 ( 21 ) : 3772 – 3789 . [CROSSREF]
  • Sheldon , R. 2001 . Ionic liquids‐new solutions for transition metal catalysis . Chem. Commun. , : 2399 – 2407 . [CROSSREF]
  • Jairton , D. , Robeerto , F. and Paulo , A. Z.S. 2002 . Ionic liquids (Molten Salts) phase organometallic catalysis . Chem. Rev. , 102 ( 10 ) : 3667 – 3692 . [CROSSREF]
  • Zhao , D. , Wu , M. , Kou , Y. and Min , E. 2002 . Ionic liquids: application in catalysis . Catalysis Today , 74 : 157 – 189 . [CROSSREF]
  • Wasserscheid , P. and Welton , T. 2002 . Ionic Liquids in Synthesis Weinheim, , Germany : VCH Wiley .
  • Earle , M. J. , McCormac , P. B. and Seddon , K. R. 1998 . Regioselective alkylation in ionic liquids . Chem. Commun. , : 2245 – 2246 . [CROSSREF]
  • Owens , G. S. and Abu‐Omer , M. M. 2002 . Comparative kinetic investigations in ionic liquids using the MTO/peroxide system . J. Mol. Catal. A: Chem. , 187 ( 2 ) : 215 – 225 . [CROSSREF]
  • Vig , O. P. , Trehan , I. R. , Kumari , S. and Grewal , M. S. 1979 . Insect juvenile hormone analogues: part IV‐synthesis of multifunctional juvenoids . Ind. J. Chem. Sect. B. , 18B ( 1 ) : 69 – 70 .
  • Calo , V. , Fiandanese , V. , Nacci , A. and Volpe , A. 1996 . Allkylated ketosulphides of benzothiazoles as intermediates for stereoselective synthesis of allyl ketones, allyl thiiranes and dienes . Tetrahedron , 52 ( 6 ) : 2155 – 2166 . [CROSSREF]

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