Abstract
Cationic gold-catalyzed cycloisomerizations of propargylureas, derived in situ from secondary propargylamines and aryl or alkyl isocyanates, have been studied. The reaction outcome was found to be different from what was previously observed for the tosyl isocyanate-derived ureas in terms of both regio- and chemoselectivity. As a result, the current protocol offers efficient access to the 3,4-dihydropyrimidin-2(1H)-one core through the 6-endo-dig N-cyclization.
| Original language | English |
|---|---|
| Pages (from-to) | 1741-1750 |
| Number of pages | 10 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 12 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Mar 21 2014 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Biochemistry
Cite this
Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas : Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones. / Pereshivko, Olga P.; Peshkov, Vsevolod A.; Peshkov, Anatoly A.; Jacobs, Jeroen; Van Meervelt, Luc; Van Der Eycken, Erik V.
In: Organic and Biomolecular Chemistry, Vol. 12, No. 11, 21.03.2014, p. 1741-1750.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas
T2 - Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones
AU - Pereshivko, Olga P.
AU - Peshkov, Vsevolod A.
AU - Peshkov, Anatoly A.
AU - Jacobs, Jeroen
AU - Van Meervelt, Luc
AU - Van Der Eycken, Erik V.
PY - 2014/3/21
Y1 - 2014/3/21
N2 - Cationic gold-catalyzed cycloisomerizations of propargylureas, derived in situ from secondary propargylamines and aryl or alkyl isocyanates, have been studied. The reaction outcome was found to be different from what was previously observed for the tosyl isocyanate-derived ureas in terms of both regio- and chemoselectivity. As a result, the current protocol offers efficient access to the 3,4-dihydropyrimidin-2(1H)-one core through the 6-endo-dig N-cyclization.
AB - Cationic gold-catalyzed cycloisomerizations of propargylureas, derived in situ from secondary propargylamines and aryl or alkyl isocyanates, have been studied. The reaction outcome was found to be different from what was previously observed for the tosyl isocyanate-derived ureas in terms of both regio- and chemoselectivity. As a result, the current protocol offers efficient access to the 3,4-dihydropyrimidin-2(1H)-one core through the 6-endo-dig N-cyclization.
UR - http://www.scopus.com/inward/record.url?scp=84894429954&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84894429954&partnerID=8YFLogxK
U2 - 10.1039/c3ob42221f
DO - 10.1039/c3ob42221f
M3 - Article
C2 - 24492944
AN - SCOPUS:84894429954
VL - 12
SP - 1741
EP - 1750
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 11
ER -