Catalytic Asymmetric Synthesis of Bicyclic Isothioureas from a Common Enolizable Template

被引：0

作者：

Villaescusa, Leire ^{[1
]}

Azcune, Laura ^{[1
]}

Landa, Aitor ^{[1
]}

Oiarbide, Mikel ^{[1
]}

机构：

[1] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Donostia San Sebastian 20018, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 21期

关键词：

DERIVATIVES; 5,5-DIPHENYL-2-THIOHYDANTOIN; DESIGN;

D O I：

10.1021/acs.joc.4c01686

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While bicyclic isothiourea (ITU) moieties are found in biologically active molecules and organocatalysts, a catalytic asymmetric synthesis of ITUs is pending. Here, we report the catalytic, enantioselective functionalization of enolizable template II with a variety of electrophiles, including unsaturated ketones, esters, sulfones, nitro compounds, and thiolating reagents, as an entry to enantioenriched bicyclic ITUs III. Scope and limitations are shown, as well as examples of product derivatization.

引用

页码：15607 / 15622

页数：16

共 37 条

[1] Thiazolo[3,2-a]benzimidazoles: Synthetic Strategies, Chemical Transformations and Biological Activities
Al-Rashood, Khalid A.
Abdel-Aziz, Hatem A.
[J]. MOLECULES, 2010, 15 (06): : 3775 - 3815
[2] Novel acetamidothiazole derivatives: Synthesis and in vitro anticancer evaluation
Ali, Ahmed R.
El-Bendary, Eman R.
Ghaly, Mariam A.
Shehata, Ihsan A.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 908 - 919
[3] Development of fluorinated and methoxylated benzothiazole derivatives as highly potent and selective cannabinoid CB2 receptor ligands
Aly, Mayar W.
Ludwig, Friedrich-Alexander
Deuther-Conrad, Winnie
Brust, Peter
Abadi, Ashraf H.
Moldovan, Rares-Petru
Osman, Noha A.
[J]. BIOORGANIC CHEMISTRY, 2021, 114
[4] Armarego W. L. F., 1988, PURIFICATION LABORAT
[5] Birman VB, 2016, ALDRICHIM ACTA, V49, P23
[6] Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist
Chaturvedi, Radha Nandan
Pendem, Krishnaiah
Patel, Vipul P.
Sharma, Mukta
Malhotra, Sunita
[J]. MONATSHEFTE FUR CHEMIE, 2018, 149 (11): : 2069 - 2084
[7] A Bifunctional Cinchona Alkaloid-Squaramide Catalyst for the Highly Enantioselective Conjugate Addition of Thiols to trans-Chalcones
Dai, Le
Wang, Su-Xi
Chen, Fen-Er
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2137 - 2141
[8] Catalytic Enantioselective Synthesis of N,C,C-Trisubstituted -Amino Acid Derivatives Using 1H-Imidazol-4(5H)-ones as Key Templates
Etxabe, Julen
Izquierdo, Joseba
Landa, Aitor
Oiarbide, Mikel
Palomo, Claudio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (23) : 6883 - 6886
[9] BENZ-FUSED MESOIONIC XANTHINE ANALOGS AS INHIBITORS OF CYCLIC-AMP PHOSPHODIESTERASE
GLENNON, RA
GAINES, JJ
ROGERS, ME
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (06) : 766 - 769
[10] Spirocyclic Scaffolds in Medicinal Chemistry
Hiesinger, Kerstin
Dar'in, Dmitry
Proschak, Ewgenij
Krasavin, Mikhail
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (01) : 150 - 183

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