Multicomponent Assembly of Trisubstituted Imidazoles and Their Photochemical Cyclization into Fused Polyheterocyclic Scaffolds

被引：10

作者：

Gapanenok, Diana ^{[1
]}

Makhmet, Azat ^{[1
,2
,3
]}

Peshkov, Anatoly A. ^{[1
]}

Smirnova, Darya ^{[1
]}

Amire, Niyaz ^{[3
]}

Peshkov, Vsevolod A. ^{[3
]}

Spiridonova, Darya ^{[1
]}

Dar'in, Dmitry ^{[1
]}

Balalaie, Saeed ^{[4
]}

Krasavin, Mikhail ^{[1
,5
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

[2] LN Gumilyov Eurasian Natl Univ, Dept Chem, Nur Sultan 010000, Kazakhstan

[3] Nazarbayev Univ, Sch Sci & Humanities, Dept Chem, Nur Sultan 010000, Kazakhstan

[4] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran 19697, Iran

[5] Immanuel Kant Baltic Fed Univ, Kaliningrad 236016, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 12期

基金：

美国国家科学基金会;

关键词：

BIGINELLI REACTION; 3-COMPONENT REACTION; DERIVATIVES; HETEROCYCLES; ALKALOIDS; EFFICIENT; CATALYST; DIHYDROPYRIMIDINONES; INDOLES; FACILE;

D O I：

10.1021/acs.joc.2c00475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward route to a large and diverse library of trisubstituted imidazoles was established via a three component reaction of 2-oxoaldehydes, 1,3-dicarbonyl compounds, and acyclic nitrogen bis-nucleophiles. The obtained products were subsequently explored in a photochemical cyclization yielding a variety of imidazole-fused polycyclic compounds.

引用

页码：7838 / 7851

页数：14

共 77 条

[1] Isocyanide-based multicomponent reactions in drug discovery
Akritopoulou-Zanze, Irini
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2008, 12 (03) : 324 - 331
[2] Imidazole as a Promising Medicinal Scaffold: Current Status and Future Direction
Alghamdi, Sahar S.
Suliman, Rasha S.
Almutairi, Khlood
Kahtani, Khawla
Aljatli, Dimah
[J]. DRUG DESIGN DEVELOPMENT AND THERAPY, 2021, 15 : 3289 - 3312
[3] Novel one-pot synthesis of new derivatives of dihydropyrimidinones, unusual multisubstituted imidazoline-2-ones: X-ray crystallography structure
Balalaie, S.
Soleiman-Beigi, M.
Rominger, F.
[J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2005, 2 (04) : 319 - 329
[4] Banfi L, 2010, TOP HETEROCYCL CHEM, V23, P1, DOI 10.1007/7081_2009_23
[5] A Bronsted acid catalysed enantioselective Biginelli reaction
Barbero, Margherita
Cadamuro, Silvano
Dughera, Stefano
[J]. GREEN CHEMISTRY, 2017, 19 (06) : 1529 - 1535
[6] The role of imidazole and benzimidazole heterocycles in Chagas disease: A review
Beltran-Hortelano, Ivan
Alcolea, Veronica
Font, Maria
Perez-Silanes, Silvia
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 206
[7] Multicomponent and One-pot Syntheses of Quinoxalines
Biesen, Lukas
Mueller, Thomas J. J.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (04) : 980 - 1006
[8] Biginelli P., 1891, BERICHTE DTSCH CHEM, V24, P1317, DOI [DOI 10.1002/CBER.189102401228, 10.1002/cber.189102401228]
[9] 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview
Bozorov, Khurshed
Zhao, Jiangyu
Aisa, Haji A.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) : 3511 - 3531
[10] Molecular Complexity as a Driver for Chemical Process Innovation in the Pharmaceutical Industry
Caille, Seb
Cui, Sheng
Faul, Margaret M.
Mennen, Steven M.
Tedrow, Jason S.
Walker, Shawn D.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08) : 4583 - 4603

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