Abstract
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.
Original language | English |
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Article number | Z21611SS |
Pages (from-to) | 1587-1594 |
Number of pages | 8 |
Journal | Synthesis |
Issue number | 10 |
DOIs | |
Publication status | Published - May 16 2011 |
Externally published | Yes |
Keywords
- 2-aminoimidazoles
- ring closure
- silver
- spiro compounds
- tandem reaction
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry