A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

Alexei Lukin, Anna Bakholdina, Anna Kryukova, Alexander Sapegin, Mikhail Krasavin

Research output

1 Citation (Scopus)

Abstract

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported basepromoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

Original languageEnglish
Pages (from-to)1061-1064
Number of pages4
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 1 Jan 2019

Scopus subject areas

  • Organic Chemistry

Cite this

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title = "A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles",
abstract = "A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported basepromoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.",
keywords = "Alkyne hydroamination, Cyclocondensation, Lewis acid catalysis, Multicomponent reactions, Propargylurea",
author = "Alexei Lukin and Anna Bakholdina and Anna Kryukova and Alexander Sapegin and Mikhail Krasavin",
year = "2019",
month = "1",
day = "1",
doi = "10.3762/bjoc.15.103",
language = "English",
volume = "15",
pages = "1061--1064",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

AU - Lukin, Alexei

AU - Bakholdina, Anna

AU - Kryukova, Anna

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

PY - 2019/1/1

Y1 - 2019/1/1

N2 - A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported basepromoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

AB - A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported basepromoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

KW - Alkyne hydroamination

KW - Cyclocondensation

KW - Lewis acid catalysis

KW - Multicomponent reactions

KW - Propargylurea

UR - http://www.scopus.com/inward/record.url?scp=85066508362&partnerID=8YFLogxK

U2 - 10.3762/bjoc.15.103

DO - 10.3762/bjoc.15.103

M3 - Article

VL - 15

SP - 1061

EP - 1064

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -