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

Research output: Contribution to journalArticle

19 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 languageEnglish
Pages (from-to)1741-1750
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number11
DOIs
Publication statusPublished - Mar 21 2014

Fingerprint

Isocyanates
Regioselectivity
isocyanates
Gold
gold
Cyclization
ureas
Urea
propargylamine
endo-alpha-sialidase

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 journalArticle

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.
@article{77d2290428874e1fb4230093a2ead868,
title = "Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones",
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.",
author = "Pereshivko, {Olga P.} and Peshkov, {Vsevolod A.} and Peshkov, {Anatoly A.} and Jeroen Jacobs and {Van Meervelt}, Luc and {Van Der Eycken}, {Erik V.}",
year = "2014",
month = "3",
day = "21",
doi = "10.1039/c3ob42221f",
language = "English",
volume = "12",
pages = "1741--1750",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "11",

}

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

VL - 12

SP - 1741

EP - 1750

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 11

ER -