Main Chain 1,5-Disubstituted-1H-Tetrazole-Based Polymers via Ugi-Azide-Four-Multicomponent Polymerization (UA-4MCP) DOI

Meryem S. Akdemir,

Birgit Huber, Marina Simian

et al.

ACS Applied Polymer Materials, Journal Year: 2023, Volume and Issue: 5(8), P. 6643 - 6650

Published: Aug. 1, 2023

The utilization of the distinctive molecular architecture tetrazoles, which comprises a five-membered ring containing four nitrogen atoms, offers tremendous potential in field polymer chemistry. Although research on pendant chain tetrazole-containing polymers has been considerably reported, exploration advanced synthesis methods for main tetrazole-based not extensively undertaken. On this premise, 1,5-disubstituted-1H-tetrazole (1,5-DS-T)-based compounds was investigated to showcase possibility formation by using Ugi-azide-four-multicomponent polymerization (UA-4MCP) strategy. Particularly, UA-4MC were designed with various side groups (e.g., aliphatic or aromatic) and engineered post-polymerization modification via thiol-ene photo-click reaction. chemical characterization confirmed 1,5-DS-T-based number average mass (Mn) up 8500 g mol–1. Importantly, side-group variation permitted tuning glass-transition temperature (Tg) between −25 60 °C. Furthermore, exhibited moderate thermal stability 305 ± 10 °C besides interesting nonconventional fluorescence behavior.

Language: Английский

Unlocking Chiral Sulfinimidoyl Electrophiles: Asymmetric Synthesis of Sulfinamides Catalyzed by Anionic Stereogenic-at-Cobalt(III) Complexes DOI
Hua‐Jie Jiang, Fang Wei, Xinran Chen

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Asymmetric catalysis involving a sulfoxide electrophile intermediate presents an efficient methodology for accessing stereogenic-at-sulfur compounds, such as sulfinate esters, sulfinamides, etc., which have garnered increasing attention in modern pharmaceutical sciences. However, the aza-analog of electrophiles, asymmetric issues about electrophilic sulfinimidoyl species remain largely unexplored and represent significant challenge sulfur stereochemistry. Herein, we exhibit anionic stereogenic-at-cobalt(III) complex-catalyzed synthesis chiral sulfinamides via iodide intermediates. Mechanistic investigations reveal that catalytic cycle is initiated by oxidative iodination, generating iodides. These active intermediates subsequently undergo enantiospecific nucleophilic substitution with water, affording diverse array enantioenriched sulfinamides. Notably, these promising antifungal activities against Sclerotinia sclerotiorum serve ideal platform molecules facilitating stereospecific transformation into various stereogenic aza-sulfur compounds.

Language: Английский

Citations

3
The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

et al.

Russian Chemical Reviews, Journal Year: 2023, Volume and Issue: 92(12), P. RCR5104 - RCR5104

Published: Dec. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Language: Английский

Citations

39
Enantioselective organocatalytic strategies to access noncanonical α-amino acids DOI Creative Commons
Pietro Pecchini, Mariafrancesca Fochi, Francesca Bartoccini

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 5832 - 5868

Published: Jan. 1, 2024

Organocatalytic asymmetric synthesis has evolved over the years and continues to attract interest of many researchers worldwide. Enantiopure noncanonical amino acids (ncAAs) are valuable building blocks in organic synthesis, medicinal chemistry, chemical biology. They employed elaboration peptides proteins with enhanced activities and/or improved properties compared their natural counterparts, as chiral catalysts, ligand design, for syntheses complex molecules, including products. The linkage ncAA enantioselective organocatalysis, subject this perspective, tries imitate biosynthetic process. Herein, we present contemporary earlier developments field organocatalytic activation simple feedstock materials, providing potential ncAAs diverse side chains, unique three-dimensional structures, a high degree functionality. These strategies, useful forging wide range C-C, C-H, C-N bonds combinations thereof, vary from classical name reactions, such Ugi, Strecker, Mannich most advanced concepts deracemisation, transamination, carbene N-H insertion. Concurrently, some interesting mechanistic studies/models, information on chirality transfer Finally, perspective highlights, through diversity (AAs) not selected by nature protein incorporation, generic modes activation, induction, reactivity commonly used, enamine, hydrogen bonding, Brønsted acids/bases, phase-transfer reflecting increasingly important role applied chemistry.

Language: Английский

Citations

7
Magnetic decorated 5-sulfosalicylic acid grafted to chitosan: A solid acid organocatalyst for green synthesis of quinazoline derivatives DOI Creative Commons

Reyhaneh Peyvasteh Sourkouhi,

Mohammad G. Dekamin, Ehsan Valiey

et al.

Carbohydrate Polymer Technologies and Applications, Journal Year: 2024, Volume and Issue: 7, P. 100420 - 100420

Published: Jan. 3, 2024

In this research, a new magnetically decorated multifunctional solid acid was designed and prepared conveniently by grafting of 5-sulfosalicylic (SSA) onto the chitosan (CS) backbone using toluene-2,4-diisocyanate (TDI) linker for first time. The obtained magnetic biopolymeric nanomaterial, CS-TDI-SSA-Fe3O4, properly characterized spectroscopic, microscopic, or analytical methods including FT-IR, EDX, XRD, BET, FESEM, TGA, VSM. supramolecular CS-TDI-SSA-Fe3O4 nanocomposite investigated, as heterogeneous organocatalyst, to promote three-component synthesis 2,3-dihydroquinazoline-4(1H)-one derivatives under green conditions. acidic nanocatalyst demonstrated highly efficient activity wide range quinazoline derivatives, an important pharmaceutical scaffold, through multicomponent strategy. reaction proceeds very well in presence EtOH afford corresponding (DHQ) high excellent yields. key advantages present protocol are use novel, renewable, biopolymeric, biodegradable simple procedure preparation hybrid material. Furthermore, catalyst can be used at least five times DHQ with slight decrease its catalytic activity.

Language: Английский

Citations

6
Recent advances in post Ugi-4CR dearomatizations for constructing spiro heterocycles DOI
Xiao Tang,

Qianqian Tao,

Liangliang Song

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4895 - 4912

Published: Jan. 1, 2024

This review summarizes recent advances in the combination of Ugi-4CR and dearomatization for synthesis spirocycles.

Language: Английский

Citations

3
A stereodivergent multicomponent approach for the synthesis of C–N atropisomeric peptide analogues DOI Creative Commons

Natalie J. Roper,

Aaron D. G. Campbell, Paul G. Waddell

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Four-component reactions at room temperature delivered C–N atropisomeric peptide analogues possessing both central and axial chirality with complete diastereocontrol. Reactions elevated selectively afforded the other diastereoisomer.

Language: Английский

Citations

3
Stereogenic-at-Cobalt(III) Complex Catalyzed Halocyclization of Alkynes: Enantioselective Access to Axially Chiralortho-Halo-C2-indoles DOI
Chuan‐Zhi Yao,

Zu‐Kui Xie,

Jie-Yue Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6146 - 6158

Published: April 6, 2023

Here, we report an anionic stereogenic-at-cobalt(III) complex catalysis strategy for the enantioselective halocyclization of ortho-alkynylanilines using N-halosuccinimide (NXS) as halogen source. This protocol provides a distinct atroposelective approach to access axially chiral ortho-halo-C2-indole skeletons in excellent yields with good high enantioselectivities (up 99% yield, 99:1 er).

Language: Английский

Citations

7
Recent developments in the total synthesis of natural products using the Ugi multicomponent reactions as the key strategy DOI
Enrique L. Larghi, Andrea B. J. Bracca, Sebastián O. Simonetti

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(3), P. 429 - 465

Published: Dec. 11, 2023

The total syntheses of selected natural products using different versions the Ugi multicomponent reaction is reviewed on a case-by-case basis. revision covers period 2008-2023 and includes detailed descriptions synthetic sequences, use state-of-the-art chemical reagents strategies, as well advantages limitations transformation some remedial solutions. Relevant data isolation bioactivity targets are also briefly provided. examples clearly evidence strategic importance this its key role in modern chemistry toolbox. This methodology proved to be valuable means for easily building molecular complexity efficiently delivering step-economic even intricate structures, with promising future.

Language: Английский

Citations

7
De novo Synthesis of Chiral 3,4‐DihydroquinazolinesviaOne‐Pot Enantioselective Ugi‐Azide/Cyclization Sequences† DOI

Zu‐Kui Xie,

Jun‐Jun Ding,

Yi‐Ming Ou

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2140 - 2146

Published: May 7, 2024

Comprehensive Summary Herein, we reported a precise de novo synthesis of chiral 3,4‐dihydroquinazoline frameworks via one‐pot anionic stereogenic‐at‐cobalt(III) complex‐catalyzed enantioselective Ugi‐azide/Pd‐catalyzed cyclization sequence. This powerful protocol involves 5 components and 2 catalytic systems, delivering 3,4‐dihydroquinazolines with excellent enantioselectivities (up to 94% ee). The preliminary antifungal experiments suggest that both Ugi‐adducts have great potential in inhibiting plant pathogens such as Trichoderma viride Fusarium graminearum .

Language: Английский

Citations

2
Loading Lewis Acid/Base Pair on Metal Nanocluster for Catalytic Ugi Reaction DOI

Jiqiang Fan,

Yanshuang Li,

Wen Wu Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Sept. 13, 2024

Constructing structurally robust and catalytically active metal nanoclusters for catalyzing multi-component reactions is an interesting while challenging task. Inspired by Lewis acid base catalysis, we realized the combination of both sites on surface a stable gold nanocluster Au

Language: Английский

Citations

2