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

被引：5

作者：

Lukin, Alexei ^{[1
]}

Bakholdina, Anna ^{[1
]}

Kryukova, Anna ^{[1
]}

Sapegin, Alexander ^{[2
]}

Krasavin, Mikhail ^{[2
]}

机构：

[1] MIREA Russian Technol Univ, Lomonosov Inst Fine Chem Technol, Moscow 119571, Russia

[2] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷

基金：

俄罗斯科学基金会;

关键词：

alkyne hydroamination; cyclocondensation; Lewis acid catalysis; multicomponent reactions; propargylurea;

D O I：

10.3762/bjoc.15.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

引用

页码：1061 / 1064

页数：4

共 7 条

[1]

Armani E., 2016, US Pat. Appl, Patent No. [US20160168101A1, 20160168101]

[2] A novel Zn-catalyzed hydroamination of propargylamides: a general synthesis of di- and tri-substituted imidazoles [J].

Pews-Davtyan, Anahit ;

Beller, Matthias .

CHEMICAL COMMUNICATIONS, 2011, 47 (07) :2152-2154

[3] A new facile synthesis of 3-amidoindole derivatives and their evaluation as potential GSK-3β inhibitors [J].

Pews-Davtyan, Anahit ;

Tillack, Annegret ;

Schmoele, Anne-Caroline ;

Ortinau, Stefanie ;

Frech, Moritz J. ;

Rolfs, Arndt ;

Beller, Matthias .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (05) :1149-1153

[4] Efficient Conversion of Tertiary Propargylamides into Imidazoles via Hydroamination-Cyclization [J].

Safrygin, Alexander ;

Krivosheyeva, Elena ;

Dar'in, Dmitry ;

Krasavin, Mikhail .

SYNTHESIS-STUTTGART, 2018, 50 (15) :3048-3058

[5]

Samajdar S., 2018, PCT Int. Appl., Patent No. [WO2015104653A1, 2015104653]

[6]

Zula A, 2013, MINI-REV MED CHEM, V13, P1921

[7]

2019, TETRAHEDRON LETT, V60, P777, DOI DOI 10.1016/J.TETLET.2019.02.011

← 1 →