Categories: Synthesis of N-Heterocycles, Synthesis of S-Heterocycles >
Synthesis of sultams and related compounds
An efficient amidation reaction of saturated C-H bonds catalyzed by a unique disilver(I) complex is reported. The reaction is stereospecific and practical for the construction of amine-containing molecules.
Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43, 4210-4212.
Highly strained β-sultams, sulfonyl analogues of β-lactams, were prepared enantio- and diastereoselectively by tertiary amine catalyzed [2 + 2] cycloaddition reactions. β-Sultams are practical precursors of highly enantioenriched β-aminosulfonyl derivatives of biological interest.
M. Zajac, R. Peters, Org. Lett., 2007, 9, 2007-2010.
Ring-closing metathesis (RCM) enables the synthesis of various of N-substituted five-membered sultams in good to excellent yields by reaction. As many sultams precipitated from the reaction mixture, an easy separation by filtration was possible.
S. Mondal, S. Debnath, Synthesis, 2014, 46, 368-374.
A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes allows access to various substituted benzosultams regioselectively in excellent yields.
S. Debnath, S. Mondal, J. Org. Chem., 2015, 80, 3940-3948.
A catalyst-free, redox-neutral, and completely atom-economical reaction enables the synthesis of sultams by simply heating 2-nitrochalcones with elemental sulfur in 3-picoline or N-methylmorpholine (NMM).
T. B. Nguyen, P. Retailleau, Org. Lett., 2017, 19, 3879-3882.