Tetrahedron最新文献_第7页

Synthesis of stagonosporyne G from (−)-D-quinic acid

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-21 DOI: 10.1016/j.tet.2025.134488

Kentaro Koyama, Hironori Okamura, Hirosato Takikawa

引用次数: 0

Exploring azetidine containing heterocycles: From green synthesis to applications

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-21 DOI: 10.1016/j.tet.2025.134491

Shivangi Jaiswal , Nikhilesh Arya , Dharma Kishore , Jaya Dwivedi , Swapnil Sharma

{"title":"Exploring azetidine containing heterocycles: From green synthesis to applications","authors":"Shivangi Jaiswal , Nikhilesh Arya , Dharma Kishore , Jaya Dwivedi , Swapnil Sharma","doi":"10.1016/j.tet.2025.134491","DOIUrl":"10.1016/j.tet.2025.134491","url":null,"abstract":"<div><div>Azetidine is a four-membered nitrogen-containing saturated heterocycle that has received significant attention in organic and medicinal chemistry research. Various FDA-approved drugs such as azelnidipine, cobimetinib, ximelagatran, and baricitinib contain azetidine moiety. The synthetic versatility of azetidine has been explored less due to its strained ring system. In the last decades, scientists have been working to advance their synthetic feasibility <em>via</em> greener routes. Thus, this review sheds light on the various green synthetic methodologies to achieve azetidine heterocycles, focusing on the high yield, stereoselective, and mild solvent/reaction medium. Importantly, an essential aspect of each synthetic strategy has been highlighted, which delves excellent insight into the desired transformation. Further, this review explores the versatile application of azetidine-based ligands in coupling reactions, asymmetric catalysis, and explosive materials. Besides, synthetic routes to FDA-approved azetidine-heterocycles have been reported, which commence the development of novel azetidine heterocycles with broader applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134491"},"PeriodicalIF":2.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342870","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Recent advances and prospects in the gold-catalyzed synthesis of oxazoles

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-21 DOI: 10.1016/j.tet.2025.134484

Kaimal Madhusoodhanan Neeraja , P. S. Devi , Gopinathan Anilkumar

{"title":"Recent advances and prospects in the gold-catalyzed synthesis of oxazoles","authors":"Kaimal Madhusoodhanan Neeraja , P. S. Devi , Gopinathan Anilkumar","doi":"10.1016/j.tet.2025.134484","DOIUrl":"10.1016/j.tet.2025.134484","url":null,"abstract":"<div><div>Oxazoles are heterocyclic compounds distinguished by a five-membered ring structure, featuring oxygen and nitrogen atoms at positions one and three. Renowned for their diverse chemical and biological properties, oxazoles hold significant value across a spectrum of disciplines including medicinal chemistry, materials science, and agrochemicals. Their ubiquitous presence underscores their pivotal role in scientific research and industrial applications alike. In the initial phases, transition metal-mediated methodologies were commonly adopted for the synthesis of oxazoles. Frequent use of these metals can pose environmental and health risks, prompting efforts to develop sustainable and environmentally benign catalytic methodologies. Gold catalysis emerges as one of the preferred greener alternatives in this context. The straightforward, diverse, and extensive chemistry demonstrated by gold renders it a highly appealing option for catalysis. Driven by its remarkable versatility and distinctive properties, we have gathered here the progress made in gold-catalyzed oxazole synthesis since 2004. The key advantages of this reaction lie in its high efficiency, chemoselectivity, regioselectivity, recyclability of the catalytic system, greater atom economy, and mild reaction setup. This review provides an overview of the Au-catalyzed oxazole synthesis covering the literature until early 2024.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134484"},"PeriodicalIF":2.1,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342943","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of cyclic carbonates from CO2 and epoxides by novel metal and halide-free chiral boron compounds

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-20 DOI: 10.1016/j.tet.2025.134485

Ahmet Kilic , Valerio D’Elia , Emine Aytar , Chalida Phungpanya , Fatma Aslanli

{"title":"Synthesis of cyclic carbonates from CO2 and epoxides by novel metal and halide-free chiral boron compounds","authors":"Ahmet Kilic , Valerio D’Elia , Emine Aytar , Chalida Phungpanya , Fatma Aslanli","doi":"10.1016/j.tet.2025.134485","DOIUrl":"10.1016/j.tet.2025.134485","url":null,"abstract":"<div><div>The production of organic cyclic carbonates as valuable chemicals was carried out using a green and sustainable catalytic strategy for the environmentally friendly metal and halide-free CO<sub>2</sub> fixation. A series of novel chiral boron compounds <strong>(B</strong><sub><strong>1</strong></sub> and <strong>B</strong><sub><strong>1a-1d</strong></sub> with <strong>B</strong><sub><strong>2</strong></sub> and <strong>B</strong><sub><strong>2a-2d</strong></sub><strong>)</strong> was synthesized, systematically characterized and applied for the synthesis of cyclic carbonates via CO<sub>2</sub> insertion into epoxides under reasonably mild reaction conditions. The prepared chiral boron compounds were characterized by NMR (<sup>1</sup>H, <sup>13</sup>C, and <sup>11</sup>B), FT-IR, UV–Vis spectroscopy, LC-MS/MS spectrometry. The thus characterized chiral boron compounds were used as Lewis acids for the cycloaddition reaction of CO<sub>2</sub> to epoxides in the presence of halide-free 4-dimethylaminopyridine (DMAP) as a nucleophilic catalytic component. Importantly, the performance of the newly synthesized compounds was also compared to that of a series of commercially available boron compounds. Halide-free commercially available boron Lewis acids generally showed lower conversion and/or selectivity under the applied reaction conditions that the newly synthesized compounds. The most active chiral boron compounds, dioxaborinanes <strong>(B</strong><sub><strong>1a</strong></sub><strong>)</strong> and <strong>(B</strong><sub><strong>1d</strong></sub><strong>)</strong>, were selective for cyclic carbonate production under atmospheric pressure and were also screened under mild CO<sub>2</sub> pressures to afford higher conversion without significantly affecting cyclic carbonate selectivity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134485"},"PeriodicalIF":2.1,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

ppm level Pd catalytic Suzuki-Miyaura coupling reaction in water and its application in the synthesis of Bixafen

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-17 DOI: 10.1016/j.tet.2025.134464

Zhiyong Tan , Tingting Chen , Jiayi Shen , Wenjun Luo , Daohong Yu , Jinbin Zhu , Minjie Zhang , Weihong Zhong , Wei Guo

引用次数: 0

Spiro-heterocycles: Recent advances in biological applications and synthetic strategies

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-17 DOI: 10.1016/j.tet.2025.134468

Basavaraja D , Siddalingeshwar V. Doddamani , Athira C. S , Aiswarya Siby , Sreelakshmi V , Ancy A , Sasidhar B. Somappa

引用次数: 0

Green and eco-compatible synthesis of quinoxaline molecules using chitosan as a biodegradable catalyst in aqueous hydrotropic medium

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-15 DOI: 10.1016/j.tet.2025.134456

Aboli C. Sapkal , Suraj R. Attar , Nilam S. Dhane , Nilesh T. Pandit , Santosh B. Kamble

{"title":"Green and eco-compatible synthesis of quinoxaline molecules using chitosan as a biodegradable catalyst in aqueous hydrotropic medium","authors":"Aboli C. Sapkal , Suraj R. Attar , Nilam S. Dhane , Nilesh T. Pandit , Santosh B. Kamble","doi":"10.1016/j.tet.2025.134456","DOIUrl":"10.1016/j.tet.2025.134456","url":null,"abstract":"<div><div>The development of green and sustainable methodologies for organic synthesis is an imperative step toward reducing the environmental impact of chemical processes. In this study, we present an efficient and eco-compatible method for the synthesis of quinoxaline derivatives using chitosan, a biodegradable and renewable catalyst, in an aqueous hydrotropic medium. Chitosan, derived from natural sources, acts as an effective biocatalyst, facilitating the reaction under mild conditions without hazardous organic solvents or harsh reagents. The use of a hydrotropic medium, specifically sodium toluene-4-sulfonate (NaPTS), enhances the solubility of reactants, leading to increased reaction rates and yields. This green approach provides significant advantages, including operational simplicity, low toxicity, and reduced waste generation. Moreover, the process is conducted in water, further promoting the sustainability of the reaction. The quinoxaline products obtained were characterized using standard spectroscopic techniques, confirming their structural integrity and purity. This method not only offers a greener alternative to traditional synthesis approaches but also aligns with the principles of green chemistry, making it suitable for large-scale applications in pharmaceutical and fine chemical industries.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134456"},"PeriodicalIF":2.1,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143315916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

One-pot multistep carboxylation–oxidation of cage compounds

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-13 DOI: 10.1016/j.tet.2025.134472

Elena A. Ivleva, Yulia E. Khatmullina, Mikhail Yu. Skomorokhov, Yuri N. Klimochkin

引用次数: 0

Effect of monosubstitution on the stability of phenylnitrene: A density functional theory study

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-12 DOI: 10.1016/j.tet.2025.134469

Juan Carlos Posadas-Hurtado , Francisco Méndez , Marco Martín González-Chávez , María de los Ángeles Zermeño-Macías

{"title":"Effect of monosubstitution on the stability of phenylnitrene: A density functional theory study","authors":"Juan Carlos Posadas-Hurtado , Francisco Méndez , Marco Martín González-Chávez , María de los Ángeles Zermeño-Macías","doi":"10.1016/j.tet.2025.134469","DOIUrl":"10.1016/j.tet.2025.134469","url":null,"abstract":"<div><div>The effect of the substituent on the stability of phenylnitrenes has impact in their application of the synthesis de aza compounds and novel materials. The energy gaps ΔE<sub>1A1–3A2</sub>, ΔE<sub>1A2–3A2</sub> and ΔE<sub>1A1–1A2</sub> for the 3A2, 1A2 and 1A1 states of <em>para</em>-, <em>meta</em>- and <em>ortho</em>-monosubstituted phenylnitrene with a set of electron-withdrawing or electron-donating substituents in the benzene ring were calculated at the DFT (M062X and B3LYP) and MP2 levels of theory and showed that the stability was 3A2>1A2>1A1. The ΔE trends ΔE<sub>1A1–3A2</sub> > ΔE<sub>1A2–3A2</sub> > ΔE<sub>1A1–1A2</sub> and ΔE<sub>1A1–3A2</sub> > ΔE<sub>1A1–1A2</sub> > ΔE<sub>1A2–3A2</sub> obtained for the electron-donating and electron-withdrawing substituents, respectively, indicated that the difference of stability between 3A2, 1A2 and 1A1 decreases as the substituent changes from electron-withdrawing to electron-donating. Electron-withdrawing substituent on <em>para-, meta-</em> and <em>ortho</em>-monosubstituted phenylnitrene causes its closed-shell singlet 1A1 to become less stable than its open-shell singlet 1A2 compared to those of phenylnitrene. The sensitive of the <em>para</em>-monosubstituted phenylnitrene to the effect of the electron-donating and electron-withdrawing substituents follows the trend ΔE<sub>1A1–1A2</sub> > ΔE<sub>1A1–3A2</sub> > ΔE<sub>1A2–3A2</sub>. Correlation analysis between the Hammett constant (σ) with the ΔE<sub>1A1–3A2</sub> and ΔE<sub>1A2–3A2</sub> reveals that substituents produce energy changes that are linearly additive, and the resonance effects are more important than inductive effects.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"173 ","pages":"Article 134469"},"PeriodicalIF":2.1,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143356341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-12 DOI: 10.1016/j.tet.2025.134467

Jiaqing Shao, Jiang Liu, Haibo Mei, Jianlin Han

引用次数: 0