Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2–POCl3 system
作者： Kiumars Bahrami , Mohammad M. Khodaei , Jamshid Abbasi
DOI: 10.1016/J.TET.2012.04.040
关键词:
摘要: Abstract Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in presence Amberlite IRA-400 (OH−). This method has been applied to a variety substrates including nucleophilic sterically hindered amines, also phenols excellent yields esters. In most cases these reactions are highly selective, simple, clean, affording products high purity.
elsevier.com
sci-hub.se 参考文章(75)
Kiumars Bahrami, Mohammad M. Khodaei, Azita Farrokhi, H2O2/SOCl2: a useful reagent system for the conversion of thiocarbonyls to carbonyl compounds Tetrahedron. ,vol. 65, pp. 7658- 7661 ,(2009) , 10.1016/J.TET.2009.06.110
Christopher G. Frost, Joseph P. Hartley, David Griffin, Catalytic Arylation of Sulfamoyl Chlorides: A Practical Synthesis of Sulfonamides Synlett. ,vol. 2002, pp. 1928- 1930 ,(2002) , 10.1055/S-2002-34907
K. Bahrami, Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride Tetrahedron Letters. ,vol. 47, pp. 2009- 2012 ,(2006) , 10.1016/J.TETLET.2006.01.051
John F. O'Connell, Henry Rapoport, 1-Benzenesulfonyl- and 1-p-toluenesulfonyl-3-methylimidazolium triflates: efficient reagents for the preparation of arylsulfonamides and arylsulfonates Journal of Organic Chemistry. ,vol. 57, pp. 4775- 4777 ,(1992) , 10.1021/JO00043A046
Kiumars Bahrami, Mohammad Khodaei, Fardin Naali, H2O2/Fe(NO3)3-PromotedSynthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles Synlett. ,vol. 2009, pp. 569- 572 ,(2009) , 10.1055/S-0028-1087911
Kiumars Bahrami, Mohammad Khodaei, Iman Kavianinia, A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles Synthesis. ,vol. 2007, pp. 547- 550 ,(2007) , 10.1055/S-2007-965878
Alan R. Katritzky, Ashraf A. A. Abdel-Fattah, Anatoliy V. Vakulenko, Hui Tao, N-sulfonylbenzotriazoles as advantageous reagents for C-sulfonylation. Journal of Organic Chemistry. ,vol. 70, pp. 9191- 9197 ,(2005) , 10.1021/JO051157I
Kiumars Bahrami, Mohammad Khodaei, Maryam Tajik, Trimethylsilyl Chloride PromotedSelective Desulfurization of Thiocarbonyls to Carbonyls with HydrogenPeroxide Synthesis. ,vol. 2010, pp. 4282- 4286 ,(2010) , 10.1055/S-0030-1258283
Kiumars Bahrami, Mohammad Khodaei, Yeganeh Tirandaz, Desulfurization of Thioamidesinto Amides with H2O2/ZrCl4 ReagentSystem Synthesis. ,vol. 2009, pp. 369- 371 ,(2009) , 10.1055/S-0028-1083314
Jerrold Meinwald, Spencer Knapp, S. Kay Obendorf, Robert E. Hughes, Single-atom peri-bridged naphthalenes. 2. Synthesis, crystal structure, and reactions of naphtho[1,8-bc]thiete derivatives Journal of the American Chemical Society. ,vol. 98, pp. 6643- 6649 ,(1976) , 10.1021/JA00437A037