N -Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of N -sulfonyl amidines
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from a 3-butyn-2-one participating CuAAC/ring-opening method. Its high reactivity due to bearing two EWGs allowed us to offer the first example of a reaction between ketenimine and amide to synthesize N-sulfonyl amidines efficiently.
A Novel Synthesis of N -Sulfonylformamidines from N Sulfonyl sulfonamides
N -Sulfonylformamidines were synthesized from N -sulfonylsulfonamides by reacting with p -toluenesulfonyl chloride (TsCl) and N, N - disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N, N -disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N -sulfonylformamidines were obtained in 60% to quantitative yields.
Mild reductive functionalization of amides into N-sulfonylformamidines
The development of a protocol for the reductive functionalization of amides into N-sulfonylformamidines is reported. The one-pot procedure is based on a mild catalytic reduction of tertiary amides into the corresponding enamines by the use of Mo(CO)6 (molybdenum hexacarbonyl) and TMDS (1,1,3,3-tetramethyldisiloxane). The formed enamines were allowed to react with sulfonyl azides to give the target compounds in moderate to good yields.
Trillo, Paz,Slagbrand, Tove,Tinnis, Fredrik,Adolfsson, Hans
p. 484 - 487
(2018/08/17)
Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity
NBS-mediated addition-elimination reaction of sulfonamides/carboxamides and formamides afforded N-sulfonylamidines and N-formylarylamides, respectively, depending on the different mechanism of elimination. Hydrogen bond-induced proton transfer leads to en
Direct condensation of sulfonamide and formamide: NaI-catalyzed synthesis of N-sulfonyl formamidine using TBHP as oxidant
A new N-sulfonyl formamidine synthesis was developed via NaI-catalyzed direct condensation of sulfonamide and formamide. The green methodology is featured by high atom economy, easily available starting materials, the lack of need for a transition-metal c
Chen, Shulin,Xu, Yuan,Wan, Xiaobing
supporting information; experimental part
p. 6152 - 6155
(2012/01/03)
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