Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols

作者: Lei Lu , Juan Ma , Panpan Qu , Feng Li

DOI: 10.1021/ACS.ORGLETT.5B00824

关键词:

摘要: A simple, highly efficient, and general strategy for the direct synthesis of amino-(N-alkyl)benzenesulfonamides has been accomplished via N-alkylation aminobenzenesulfonamides bearing both different types amino groups with alcohols as alkylating agents. Notably, this research exhibited potential recognition in complex molecules alcohols, facilitating progress transition-metal-catalyzed “hydrogen autotransfer (or hydrogen-borrowing) process.”

参考文章(46)
Ken-ichi Fujita, Shigetoyo Furukawa, Ryohei Yamaguchi, Oxidation of primary and secondary alcohols catalyzed by a pentamethylcyclopentadienyliridium complex Journal of Organometallic Chemistry. ,vol. 649, pp. 289- 292 ,(2002) , 10.1016/S0022-328X(01)01461-9
Takeyuki Suzuki, Organic synthesis involving iridium-catalyzed oxidation. Chemical Reviews. ,vol. 111, pp. 1825- 1845 ,(2011) , 10.1021/CR100378R
Arun K. Ghosh, Bruno D. Chapsal, Garth L. Parham, Melinda Steffey, Johnson Agniswamy, Yuan-Fang Wang, Masayuki Amano, Irene T. Weber, Hiroaki Mitsuya, Design of HIV-1 Protease Inhibitors with C3-Substituted Hexahydrocyclopentafuranyl Urethanes as P2-Ligands: Synthesis, Biological Evaluation, and Protein–Ligand X-ray Crystal Structure Journal of Medicinal Chemistry. ,vol. 54, pp. 5890- 5901 ,(2011) , 10.1021/JM200649P
Johnson Agniswamy, Chen-Hsiang Shen, Yuan-Fang Wang, Arun K. Ghosh, Kalapala Venkateswara Rao, Chun-Xiao Xu, Jane M. Sayer, John M. Louis, Irene T. Weber, Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran. Journal of Medicinal Chemistry. ,vol. 56, pp. 4017- 4027 ,(2013) , 10.1021/JM400231V
Sebastian Imm, Sebastian Bähn, Min Zhang, Lorenz Neubert, Helfried Neumann, Florian Klasovsky, Jan Pfeffer, Thomas Haas, Matthias Beller, Improved Ruthenium-Catalyzed Amination of Alcohols with Ammonia: Synthesis of Diamines and Amino Esters Angewandte Chemie International Edition. ,vol. 50, pp. 7599- 7603 ,(2011) , 10.1002/ANIE.201103199
Elisabeth-Maria Bissinger, Ralf Heinke, Astrid Spannhoff, Adrien Eberlin, Eric Metzger, Vincent Cura, Pierre Hassenboehler, Jean Cavarelli, Roland Schüle, Mark T. Bedford, Wolfgang Sippl, Manfred Jung, Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1. Bioorganic & Medicinal Chemistry. ,vol. 19, pp. 3717- 3731 ,(2011) , 10.1016/J.BMC.2011.02.032
M Haniti SA Hamid, C Liana Allen, Gareth W Lamb, Aoife C Maxwell, Hannah C Maytum, Andrew JA Watson, Jonathan MJ Williams, None, Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology. Journal of the American Chemical Society. ,vol. 131, pp. 1766- 1774 ,(2009) , 10.1021/JA807323A
Amparo Prades, Rosa Corberán, Macarena Poyatos, Eduardo Peris, [IrCl2Cp*(NHC)] Complexes as Highly Versatile Efficient Catalysts for the Cross‐Coupling of Alcohols and Amines Chemistry: A European Journal. ,vol. 14, pp. 11474- 11479 ,(2008) , 10.1002/CHEM.200801580
Feng Shi, Man Kin Tse, Shaolin Zhou, Marga-Martina Pohl, Jörg Radnik, Sandra Hübner, Klaus Jähnisch, Angelika Brückner, Matthias Beller, Green and Efficient Synthesis of Sulfonamides Catalyzed by Nano-Ru/Fe3O4 Journal of the American Chemical Society. ,vol. 131, pp. 1775- 1779 ,(2009) , 10.1021/JA807681V