Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones

Olga P. Pereshivko; Vsevolod A. Peshkov; Anatoly A. Peshkov; Jeroen Jacobs; Luc Van Meervelt; Erik V. Van Der Eycken

doi:10.1039/c3ob42221f

Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones

Olga P. Pereshivko, Vsevolod A. Peshkov, Anatoly A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Erik V. Van Der Eycken

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

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	https://doi.org/10.1039/c3ob42221f
Publication status	Published - Mar 21 2014

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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10.1039/c3ob42221f

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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 › peer-review

Pereshivko, Olga P. ; Peshkov, Vsevolod A. ; Peshkov, Anatoly A. ; Jacobs, Jeroen ; Van Meervelt, Luc ; Van Der Eycken, Erik V. / Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas : Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 11. pp. 1741-1750.

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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.",

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AU - Jacobs, Jeroen

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