18402-34-1Relevant academic research and scientific papers
Photo Click Reaction of Acylsilanes with Indoles
Stuckhardt, Constantin,Studer, Armido,Wissing, Maren
supporting information, p. 18605 - 18611 (2021/07/26)
Light-mediated coupling of acylsilanes with indoles is reported. This photo click reaction occurs under mild conditions (415 nm) mostly in quantitative yield and provides stable silylated N,O-acetals via light mediated siloxycarbene generation with subsequent indole-N-H insertion. We show that this very efficient and fully atom economic coupling process can be applied to conjugate complex systems, as documented by the clicking of carbohydrates with indole alkaloids. The method is also applicable to the conjugation of polymer chains. The linking acetal moiety can be readily cleaved and it is also shown that wavelength-selective coupling and cleavage with acyl silanes bearing a second photoactive moiety is possible. This is documented by a successful polymerization/depolymerization sequence and by a polymer folding/unfolding process.
N-SUBSTITUTED DERIVATIVES OF 2-PYRROLIDONE IN THE SILYL METHOD OF C- AND N-AMIDOALKYLATION
Shipov, A. G.,Zheltonogova, E. A.,Kobzareva, V. P.,Orlova, N. A.,Baukov, Yu. I.
, p. 2142 - 2150 (2007/10/02)
With O-silyl-substituted enols and 1-trimethylsilyl-2-pyrrolidone in the presence of catalytic amounts of trimethylsilyl triflate under mild conditions the adducts of 1-trimethylsilyl-2-pyrrolidone with benzaldehyde and furfural form the products from C- and N-amidoalkylation respectively.The N- and C-amidoalkylation products containing an ethoxycarbonyl group at the electrophilic center can be obtained by the reaction of 1-(1-chloro-1-ethoxycarbonylmethyl)-2-pyrrolidone with the above-mentioned organosilicon nucleophiles.In the reaction of 2-pyrrolidone, ethyl glyoxalate, and dimethylchlorosilane in the presence of stannic chloride reductive alkylation of the 1-lactam acetic ester occurs.
