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Highly efficient Cu(acac)2 catalyzed multi component synthesis of 1,4-disubstituted-1,2,3-triazoles using aryl halide/ phenyl boronic acid or styrene oxide and aryl alkynes with sodium azide in aqueous medium
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-04-02 DOI: 10.1016/j.tet.2025.134629
Upendra Pappula, Venkata Prasad Kalyana, Ujjal Kanti Roy
{"title":"Highly efficient Cu(acac)2 catalyzed multi component synthesis of 1,4-disubstituted-1,2,3-triazoles using aryl halide/ phenyl boronic acid or styrene oxide and aryl alkynes with sodium azide in aqueous medium","authors":"Upendra Pappula,&nbsp;Venkata Prasad Kalyana,&nbsp;Ujjal Kanti Roy","doi":"10.1016/j.tet.2025.134629","DOIUrl":"10.1016/j.tet.2025.134629","url":null,"abstract":"<div><div>The sequential three-component reaction of aryl halide/phenyl boronic acid or styrene oxide, with sodium azide and alkynes using copper catalysis has been discussed. The reaction proceeds <em>via</em> the in-situ generation of aryl azide/azido-alcohol followed by synthesis of 1,4-disubstituted-1,2,3-triazoles/<em>β</em>-hydroxy-triazoles. Relatively inert aryl halides are smoothly activated by the catalyst to form aryl azide s<em>in situ</em>. The multicomponent approach of the reaction makes it efficient, easy to perform and variety of functional group tolerant. This copper-catalyzed aqueous [3 + 2] azide−alkyne cycloaddition (CuAAC) reactions of <em>in situ</em> generated aryl azide/azido-alcohol and alkyne using commercially and readily available Cu(acac)<sub>2</sub> catalyst serves as an efficient protocol in ‘‘Click Chemistry’‘.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134629"},"PeriodicalIF":2.1,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143799859","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 synthesis and mechanistic insights of quinazoline and related molecules
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-31 DOI: 10.1016/j.tet.2025.134635
Pragati Kushwaha, Ayush Bhardwaj, Rashi
{"title":"One pot synthesis and mechanistic insights of quinazoline and related molecules","authors":"Pragati Kushwaha,&nbsp;Ayush Bhardwaj,&nbsp;Rashi","doi":"10.1016/j.tet.2025.134635","DOIUrl":"10.1016/j.tet.2025.134635","url":null,"abstract":"<div><div>One-pot synthesis of quinazoline derivatives has emerged as a highly efficient and sustainable strategy for the preparation of these bioactive compounds. This review highlights the recent advancements in the one-pot synthetic routes to quinazoline and its derivatives. It emphasises on the development of efficient catalysts including transition metal, organo-catalyst, and environmental friendly reagents, which will significantly improve reaction selectivity and yields. Ultimately, this review provides an in-depth overview of the progress, mechanistic pathways, challenges, and future prospects of one-pot synthesis of quinazoline and related molecules, highlighting the potential of this approach to revolutionize synthetic organic chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134635"},"PeriodicalIF":2.1,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791506","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 in direct asymmetric reaction of furanone 呋喃酮直接不对称反应的最新进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-29 DOI: 10.1016/j.tet.2025.134627
Ling Zhang , Qiang Zhang , Ran Wang , Aiqin Liu , Manfei Liang , Zhushuang Bai
{"title":"Recent advances in direct asymmetric reaction of furanone","authors":"Ling Zhang ,&nbsp;Qiang Zhang ,&nbsp;Ran Wang ,&nbsp;Aiqin Liu ,&nbsp;Manfei Liang ,&nbsp;Zhushuang Bai","doi":"10.1016/j.tet.2025.134627","DOIUrl":"10.1016/j.tet.2025.134627","url":null,"abstract":"<div><div>Butenoic acid compounds or γ-butyrolactone compounds containing multiple chiral centers widely exist in various natural products and have very important biological activities, such as anti-tumor activity. However, the scarcity of many highly active natural compounds restricts their potential for further research into biological functions and therapeutic applications. Therefore, new methods are required for the efficient synthesis of these compounds. Direct catalytic asymmetric reactions based on furanone have emerged as a promising approach for the quick construction of chiral poly-substituted compounds, enabling the synthesis of biologically active natural products, analogues, and bio-active molecules. In this review, we will explore recent developments in direct catalytic asymmetric reactions based on furanone and their applications in the synthesis of natural products and bioactive molecules.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134627"},"PeriodicalIF":2.1,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143816598","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
A heterogeneous MOF-253-based Pd/Cu bimetal for Sonogashira coupling reactions
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-29 DOI: 10.1016/j.tet.2025.134628
Ningtao Cao , Yue Tong , Jianwei Xie , Shaofeng Gong
{"title":"A heterogeneous MOF-253-based Pd/Cu bimetal for Sonogashira coupling reactions","authors":"Ningtao Cao ,&nbsp;Yue Tong ,&nbsp;Jianwei Xie ,&nbsp;Shaofeng Gong","doi":"10.1016/j.tet.2025.134628","DOIUrl":"10.1016/j.tet.2025.134628","url":null,"abstract":"<div><div>Here we reported a MOF-based bimetal catalyst, Cu-MOF-253-Pd, as an efficient, robust and recyclable catalyst for Sonogashira coupling reaction between (hetero)aryl halides and terminal alkynes for the preparation of di-substituted acetylenes. Broad substrate scope, including late-stage functionalization of complex molecule, has been demonstrated, and the synthetic applications further displayed high turnover numbers up to 4794, scalability, recyclability and robustness of the reaction system.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134628"},"PeriodicalIF":2.1,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738021","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
A critical review on the sustainable synthesis of pyrimidine-based heterocycles and their biological activities
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-29 DOI: 10.1016/j.tet.2025.134626
Viphrezolie Sorhie , Tsenbeni N. Lotha , Susital Mal , Subrata Das , Latonglila Jamir , Pranjal Bharali
{"title":"A critical review on the sustainable synthesis of pyrimidine-based heterocycles and their biological activities","authors":"Viphrezolie Sorhie ,&nbsp;Tsenbeni N. Lotha ,&nbsp;Susital Mal ,&nbsp;Subrata Das ,&nbsp;Latonglila Jamir ,&nbsp;Pranjal Bharali","doi":"10.1016/j.tet.2025.134626","DOIUrl":"10.1016/j.tet.2025.134626","url":null,"abstract":"<div><div>Pyrimidine scaffolds exhibit diverse biological and pharmacological activities, serving as inhibitors of specific biological systems and demonstrating analgesic, antiviral, antibacterial, antifungal, and anticonvulsant properties. A vast array of structurally significant derivatives, encompassing scaffolds generated via aryl ring substitution or by the derivatization at N1, N3, C5, and C6 positions of the pyrimidine ring, were produced as a result of the synthetic diversity of pyrimidines. The versatile nature of pyrimidines allow chemists to synthetically formulate and produce novel moieties through different synthetic routes. Recent developments in synthetic strategies have emphasized greener, more sustainable methods, such as microwave-assisted synthesis, one-pot reactions, ultrasonification, photochemical, electrochemical and metal-catalyzed cross-coupling reactions. Furthermore, bioinspired approaches and the use of renewable resources are gaining popularity in the synthesis of functionalized pyrimidines which have also been explored. This review aims to systematically evaluate both conventional and eco-friendly approaches for synthesizing these scaffolds, while also highlighting recent discoveries and technological advancements in their production. The pharmacological properties of various substituted pyrimidines, along with an exploration of their synthesis methods, provide a foundation for studying their future structure-activity relationships and mechanisms of action.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134626"},"PeriodicalIF":2.1,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776801","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 advancement on metal free hydroamination reaction of C–C multiple bonds
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-28 DOI: 10.1016/j.tet.2025.134625
Pamela Pal , Sayanti Show , Sukanya Das , Sriyanka Bhandari , Sushmita Nandy , Md. Abbasuddin Sk , Raj Kumar Nandi
{"title":"Recent advancement on metal free hydroamination reaction of C–C multiple bonds","authors":"Pamela Pal ,&nbsp;Sayanti Show ,&nbsp;Sukanya Das ,&nbsp;Sriyanka Bhandari ,&nbsp;Sushmita Nandy ,&nbsp;Md. Abbasuddin Sk ,&nbsp;Raj Kumar Nandi","doi":"10.1016/j.tet.2025.134625","DOIUrl":"10.1016/j.tet.2025.134625","url":null,"abstract":"<div><div>Hydroamination is an essential tool in organic synthesis because it facilitates the addition of amines to unsaturated hydrocarbons. Metal-free hydroamination reactions are a significant advancement in organic synthesis, enabling for both intra- and intermolecular processes employing unactivated C–C multiple bonds to form C–N bonds. We documented the reported literature methods, which provided an environmentally acceptable and cost-effective alternative to standard metal-catalyzed hydroamination reactions. This review focuses on the substrate range, functional group tolerance, and mechanistic understanding of diverse tactics, such as the utilization of Lewis acids, organic bases, iodine catalysts, photochemical and electrochemical approaches. Finally, this review aims to provide an in-depth analysis of the most recent advances in metal-free hydroamination reported between 2014 and 2024, highlighting its promise for sustainable chemistry with an emphasis on the production of fine chemicals and pharmaceutically impactful products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134625"},"PeriodicalIF":2.1,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738066","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
A fluorescent probe with large Stokes shift for detecting biothiols in living cells and zebrafish
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-28 DOI: 10.1016/j.tet.2025.134615
Zhao Wang , Zhenbo Gao , Yue Gao , Xiaomeng Pang , Xiaofeng Xia
{"title":"A fluorescent probe with large Stokes shift for detecting biothiols in living cells and zebrafish","authors":"Zhao Wang ,&nbsp;Zhenbo Gao ,&nbsp;Yue Gao ,&nbsp;Xiaomeng Pang ,&nbsp;Xiaofeng Xia","doi":"10.1016/j.tet.2025.134615","DOIUrl":"10.1016/j.tet.2025.134615","url":null,"abstract":"<div><div>Abnormal levels of biothiols in organisms can cause physiological disorders, which are closely associated with the occurrence and development of various diseases. Therefore, a novel fluorescent probe (TMN-Cl-S) with large Stokes shift was designed for in vivo detection of biothiols. The probe was characterized by a large Stokes shift (150 nm) and displayed a prominent activation response at physiological pH, enabling highly selective and sensitive detection of Cys, Hcy and GSH. Furthermore, the probe exhibited high stability, low cytotoxicity, and good cell membrane permeability, hence it was available for imaging biothiols in living cells and zebrafish.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134615"},"PeriodicalIF":2.1,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738067","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
Highly planar ground triplet biradical 5-trifluoromethyl-1,3-phenylene bis(tert-butyl nitroxide) testing the limit of stabilization
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-28 DOI: 10.1016/j.tet.2025.134614
Nagito Haga, Takayuki Ishida
{"title":"Highly planar ground triplet biradical 5-trifluoromethyl-1,3-phenylene bis(tert-butyl nitroxide) testing the limit of stabilization","authors":"Nagito Haga,&nbsp;Takayuki Ishida","doi":"10.1016/j.tet.2025.134614","DOIUrl":"10.1016/j.tet.2025.134614","url":null,"abstract":"<div><div>The magnetic study on newly developed 5-trifluoromethyl-1,3-phenylene bis(<em>tert</em>-butyl nitroxide) clarified the ground triplet state. Although it can be isolated under ambient conditions, a diamagnetic dimerized product was given, after the benzene rings underwent a [3 + 3] cycloaddition. The ability of complex formation was proven with Gd<sup>3+</sup>, giving a metal-ligand alternating chain compound. The DFT calculation work clearly indicates that this biradical is a robust triplet ligand. The much low-lying triplet state originates in the planar molecular skeleton, thanks to the less hindered <em>m</em>-trifluoromethyl group. From the empirical viewpoint, CF<sub>3</sub> has an unexpectedly stronger stabilizing effect than Ph but weaker than <em>t</em>-Bu, when located at the <em>m</em>-position with respect to the nitroxide group.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134614"},"PeriodicalIF":2.1,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143759994","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
Large multifunctional triphenylamine derivatives as versatile candidates for porous supramolecular materials 作为多孔超分子材料多功能候选材料的大型多功能三苯胺衍生物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-28 DOI: 10.1016/j.tet.2025.134630
Nadia Maté , Elena Bogdan , Lidia Căta , Anamaria Terec , Arie van der Lee , Mihail Bӑrboiu , Niculina D. Hӑdade , Ion Grosu
{"title":"Large multifunctional triphenylamine derivatives as versatile candidates for porous supramolecular materials","authors":"Nadia Maté ,&nbsp;Elena Bogdan ,&nbsp;Lidia Căta ,&nbsp;Anamaria Terec ,&nbsp;Arie van der Lee ,&nbsp;Mihail Bӑrboiu ,&nbsp;Niculina D. Hӑdade ,&nbsp;Ion Grosu","doi":"10.1016/j.tet.2025.134630","DOIUrl":"10.1016/j.tet.2025.134630","url":null,"abstract":"<div><div>The access to novel triphenyl-, tris(biphenyl)- and tris(phenyl-ethynyl-phenyl)amine derivatives decorated with bromine, carboxy or hydroxymethyl groups is developed based on aliphatic nucleophilic substitution and Suzuki-Miyaura and Sonogashira cross-coupling reactions. The target compounds decorated with various groups are able to participate to the formation of self-assembled architectures by hydrogen or halogen bonding.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"178 ","pages":"Article 134630"},"PeriodicalIF":2.1,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143735118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Catalyst- and solvent-free hydrosulfonylation of alkenes with sulfinates enabling green synthesis of β-sulfonyl amides
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-03-28 DOI: 10.1016/j.tet.2025.134632
Dan Luo, Qian Wang, Haibo Mei, Jianlin Han
{"title":"Catalyst- and solvent-free hydrosulfonylation of alkenes with sulfinates enabling green synthesis of β-sulfonyl amides","authors":"Dan Luo,&nbsp;Qian Wang,&nbsp;Haibo Mei,&nbsp;Jianlin Han","doi":"10.1016/j.tet.2025.134632","DOIUrl":"10.1016/j.tet.2025.134632","url":null,"abstract":"<div><div>An efficient hydrosulfonylation reaction of alkenes with sodium sulfinates as Michael donors has been developed, which affords β-sulfonyl amides as products with up to 99 % yield. This reaction was conducted under mild conditions without the need of any catalyst, in particular, no solvent was needed for this transformation. This reaction represents the first example of hydrosulfonylation reaction with sodium sulfinates under neat conditions. Moreover, this reaction features wide range of structurally diverse alkenes and sodium sulfinates, which provides a green and valuable strategy for the synthesis of β-sulfonyl amides.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"179 ","pages":"Article 134632"},"PeriodicalIF":2.1,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738022","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
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