1316844-77-5Relevant academic research and scientific papers
Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles
Pereshivko, Olga P.,Peshkov, Vsevolod A.,Ermolatev, Denis S.,Van Hove, Sofie,Van Hecke, Kristof,Van Meervelt, Luc,Van Der Eycken, Erik V.
, p. 1587 - 1594 (2011)
A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles. Georg Thieme Verlag Stuttgart · New York.
α-Tertiary Propargylamine Synthesis via KA2-Type Coupling Reactions under Solvent-Free CuI-Zeolite Catalysis
Bénéteau, Valérie,Chassaing, Stefan,Pale, Patrick,Plac?is, Clotilde,Schlimpen, Fabian,Starck, Eliot
, p. 16593 - 16613 (2021/12/06)
The potential of copper(I)-zeolite catalysis was evaluated in the three-component KA2-coupling mediated synthesis of α-tertiary propargylamines. Our archetypal copper(I)-doped zeolite CuI-USY proved to be efficient under ligand- A nd solvent-free conditions at 80 °C. Usable up to four times, this catalytic material enables the coupling of diverse ketones, alkynes, and amines with a broad functional group tolerance. A decarboxylative and a desilylative version, respectively, involving an alkynoic acid and trimethylsilylacetylene as alkyne surrogates, was also set up to bypass selectivity issues and/or to access α-tertiary propargylamines that are unattainable under standard KA2 conditions. Interestingly, the KA2-type coupling reactions were successfully linked to other CuI-catalyzed reactions, thus resulting in sequential one-pot processes under full CuI-USY catalysis.
