Diversity-Oriented Silver(I)-Mediated Synthesis of Spiro-2-aminoimidazoles

作者：Pereshivko Olga P; Peshkov Vsevolod A; Ermolat'ev Denis S^*; Van Hove Sofie; Van Hecke Kristof; Van Meervelt Luc; Van der Eycken Erik V

来源：Synthesis (Germany), 2011, 2011(10): 1587-1594.

DOI：10.1055/s-0030-1260012

• 2-aminoimidazoles
• spiro compounds
• tandem reaction
• ring closure
• silver

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.

• 出版日期2011-5