3989-48-8Relevant articles and documents
A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines
Shvets, Elena H.,Pidvorotnia, Anastasiia V.,Kulyk, Olesia G.,Mazepa, Alexander V.,Kolosov, Maksim A.
supporting information, p. 114 - 122 (2020/10/02)
4,7-Dihydroazolo[1,5-a]pyrimidin-5-ylmethanesulfonamides are side-products of the three-component Biginelli-like reaction of aminoazoles, aldehydes and N,N-dialkyl-2-ketomethanesulfonamides. Herein, we report a straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines by a two-component condensation of aminoazoles and N,N-dialkyl(cinnamoyl)methanesulfonamides in DMF at reflux. The starting N,N-dialkyl-2-ketomethanesulfonamides can be obtained by either lithiation of N,N-dialkylmethanesulfonamides and reaction with aldehydes followed by oxidation of the resulting alcohols or by Claisen condensation of N,N-dialkylmethanesulfonamides with the corresponding esters. The chemical structures of all synthesized compounds are supported by 1H and 13C NMR-spectroscopy, mass spectrometry and elemental analysis.
Highly enantioselective transfer hydrogenation of racemic α-substituted β-keto sulfonamides: Via dynamic kinetic resolution
Xiong, Zhichao,Pei, Chengfeng,Xue, Peng,Lv, Hui,Zhang, Xumu
supporting information, p. 3883 - 3886 (2018/04/20)
Highly enantioselective transfer hydrogenation of β-keto sulfonamides was developed via dynamic kinetic resolution using a chiral Ru(ii) catalyst with an azeotropic solution of HCO2H/Et3N as a hydrogen donor, affording α-substituted β-hydroxyl sulfonamides in good yields with excellent diastereo- and enantioselectivities. This method is featured with mild conditions, easy operation, and a broad substrate scope, which make it possible to find wide applications in the synthesis of natural products and biologically active compounds containing the α-substituted β-hydroxyl sulfonamide core.
DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents
Jones, Caroline S.,Bull, Steven D.,Williams, Jonathan M. J.
supporting information, p. 8452 - 8456 (2016/09/28)
Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.