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 |
|---|---|
| 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 |
Fingerprint
Keywords
- 2-aminoimidazoles
- ring closure
- silver
- spiro compounds
- tandem reaction
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
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.
In: Synthesis, No. 10, Z21611SS, 16.05.2011, p. 1587-1594.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles
AU - Pereshivko, Olga P.
AU - Peshkov, Vsevolod A.
AU - Ermolatev, Denis S.
AU - Van Hove, Sofie
AU - Van Hecke, Kristof
AU - Van Meervelt, Luc
AU - Van Der Eycken, Erik V.
PY - 2011/5/16
Y1 - 2011/5/16
N2 - 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.
AB - 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.
KW - 2-aminoimidazoles
KW - ring closure
KW - silver
KW - spiro compounds
KW - tandem reaction
UR - http://www.scopus.com/inward/record.url?scp=79955872035&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79955872035&partnerID=8YFLogxK
U2 - 10.1055/s-0030-1260012
DO - 10.1055/s-0030-1260012
M3 - Article
AN - SCOPUS:79955872035
SP - 1587
EP - 1594
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 10
M1 - Z21611SS
ER -