365441-83-4Relevant articles and documents
Leaving group and regioselectivity switches in the aminoalkylation reaction of indoles and related heterocycles with α-amido sulfones
Blay, Gonzalo,Giron, Rosa M.,Montesinos-Magraner, Marc,Pedro, Jose R.
supporting information, p. 3885 - 3895 (2013/07/19)
The regioselective aminoalkylation of indoles and related heterocycles with α-amido sulfones under basic conditions has been studied. The reaction that employed the MeMgBr/MgBr2 system provided high yields of 3-(1-carbamoylalkyl)indoles. On the other hand, the reaction that used Cs 2CO3 afforded 1-(1-carbamoylalkyl)indoles exclusively in high yields. The first reaction constitutes a switch of the leaving group of the α-amido sulfone in comparison to previously reported reactions between indoles and α-amido sulfones, which provided 3-(1-arylsulfonylalkyl) indoles. The second reaction constitutes a switch in the regioselectivity. The extensions of these C- and N-aminoalkylations starting from pyrroles and 7-azaindole have also been studied. Structurally diverse aminoalkylated indoles, pyrroles, and 7-azaindoles were obtained with excellent yield in most of the cases. The regioselective aminoalkylation of indoles and heterocycles with α-amido sulfones under basic conditions is described. The reaction with MeMgBr/MgBr2 gives 3-(1-carbamoylalkyl)indoles, whereas employing Cs2CO3 yields 1-(1-carbamoylalkyl)indoles. The first case presents a switch of the leaving group of the α-amido sulfone, whereas the second demonstrates a switch in the regioselectivity. Copyright
Reductive BOC-amination of aldehydes
Bernacka, Elbieta,Klepacz, Anna,Zwierzak, Andrzej
, p. 5093 - 5094 (2007/10/03)
Base-assisted elimination-reduction of α-amidoalkyl sulfones with sodium borohydride proceeds in tetrahydrofuran at room temperature leading to the corresponding BOC-amines in good yields.