1600517-92-7Relevant academic research and scientific papers
Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration
Bernar, Ivan,Blanco-Ania, Daniel,Stok, Sophie J.,Sotorríos, Lia,Gómez-Bengoa, Enrique,Rutjes, Floris P. J. T.
, p. 5435 - 5444 (2018/10/20)
A completely regioselective and highly stereoselective palladium-catalyzed intramolecular hydroarylation of arenesulfonyl ynamines to benzothiazoles was developed. The presence of an electron-withdrawing group on the triple bond of the sulfonyl ynamine was crucial for the success of the reaction and our mechanistic studies suggest an alkyne-directed 5-exo-dig cyclization pathway. The products easily underwent photoinduced rearrangement to 3-amino-1-benzothiophene-1,1-diones (up to 35 % yields after two steps).
Gold(I)-Catalyzed 1,3-O-Transposition Reactions: Ynesulfonamides to Ynamides
Li, De-Yao,Wei, Yin,Shi, Min
supporting information, p. 4108 - 4113 (2015/06/30)
The gold-catalyzed 1,3-O-transposition reaction of ynesulfonamides provides a practical synthetic protocol for the synthesis of ynamides under mild conditions. This is the first 1,3-O-transposition example of ynesulfonamides in which a heteroatom is attached to the alkynyl terminal. A plausible mechanism is been proposed on the basis of 18O-labeling and control experiments as well as DFT calculation. By simple treatment, the obtained ynamides can easily be transformed into useful products. The gold-catalyzed 1,3-O-transposition reaction of ynesulfonamides provides a practical synthetic protocol for the synthesis of ynamides under mild conditions. This is the first 1,3-O-transposition example of ynesulfonamides in which a heteroatom is attached to the alkynyl terminal.
Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles
Zhang, Peng,Cook, Andrea M.,Liu, Yang,Wolf, Christian
, p. 4167 - 4173 (2014/05/20)
The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon-carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield.
