Tetrahedron最新文献_第6页

Unprecedented synthesis of indole-linked tetra-substituted alkenes by catalyst-free domino reaction 通过无催化剂多米诺反应前所未有地合成吲哚连接的四取代烯烃

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-24 DOI: 10.1016/j.tet.2024.134327

Darakshan, Ujjain Chaurasia, Aatka Mehar, Tasneem Parvin

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Synthesis and investigation of photo-physical properties of fluorescent dyes obtained by the Knoevenagel condensation of mono-, di- or tri-formyl aromatic aldehydes and various CH-acid derivatives 通过单、二或三芳基芳香醛与各种 CH 酸衍生物的 Knoevenagel 缩合获得的荧光染料的合成及其光物理特性研究

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-24 DOI: 10.1016/j.tet.2024.134325

A. Pałasz, P. Goszczycki, D. Cież, A. Błaszków, A. Marchewka, M. Ogos, D. Barczyk

{"title":"Synthesis and investigation of photo-physical properties of fluorescent dyes obtained by the Knoevenagel condensation of mono-, di- or tri-formyl aromatic aldehydes and various CH-acid derivatives","authors":"A. Pałasz, P. Goszczycki, D. Cież, A. Błaszków, A. Marchewka, M. Ogos, D. Barczyk","doi":"10.1016/j.tet.2024.134325","DOIUrl":"10.1016/j.tet.2024.134325","url":null,"abstract":"<div><div>Fluorescent dyes were constructed using the Knoevenagel condensation of the appropriate aldehydes and CH-acid derivatives. Aromatic aldehydes containing one, two or three formyl groups were used as substrates. Cyanoacetamide, ethyl cyanoacetate, benzoylacetonitrile and indan-1,3-dione play the role of CH-acid derivative. The appropriate aldehydes were obtained by the Duff formylation reaction. The dyes synthesis procedure was very simple. The condensation was carried out in water in the presence of NaOH, as the basic catalyst at room temperature, and the dyes were obtained in yields between 58 and 93 %. The work-up procedure was very simple, and the products do not require any further purification. The great advantages of this synthetic procedure are its simplicity, cheapness, compliance with the rules of green chemistry and the fact that it efficiently leads to structurally complex fluorescent dyes. Twenty-three new compounds were obtained, eleven of which exhibited fluorescence in solution and four in the solid state. Taking into account the fluorescence quantum yield and the emission maximum value close to the NIR range, the dye constructed by condensation of indan-1,3-dione and methyl 3,5-diformyl-4-hydroxybenzoate meets the above-mentioned requirements (Φ = 16 %, λ<sub>em</sub> = 660 nm) best. The dye with the highest value of Φ = 25 % in solid is a derivative of cyanoacetamide and 3,4,5-trimethoxybenzaldehyde.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134325"},"PeriodicalIF":2.1,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142555539","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}

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Approach to extended polycyclic aromatic hydrocarbons by benzannulation and intramolecular cyclization; improvement of the reaction conditions by microwave irradiation 通过苯annulation 和分子内环化反应制备扩展的多环芳烃；利用微波辐照改善反应条件

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-24 DOI: 10.1016/j.tet.2024.134332

Rui Umeda, Raiki Nishikawa, Taketo Matsui, Kotaro Takase

引用次数: 0

Paradigm shift in medicinal products synthesis: Continuous flow technology 药用产品合成的范式转变：连续流技术

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-24 DOI: 10.1016/j.tet.2024.134333

Bryce L. Koeberg , Mellisa B. Sagandira , Cloudius R. Sagandira , Paul Watts

{"title":"Paradigm shift in medicinal products synthesis: Continuous flow technology","authors":"Bryce L. Koeberg , Mellisa B. Sagandira , Cloudius R. Sagandira , Paul Watts","doi":"10.1016/j.tet.2024.134333","DOIUrl":"10.1016/j.tet.2024.134333","url":null,"abstract":"<div><div>About 80 % of the population in developing economies such as Africa use traditional medicines for healthcare. Traditional medicines from diverse cultures have been recognized for their efficacy and cost-effectiveness in improving health in developing economies. Access to synthetic natural products is typically associated with challenges such as lengthy synthetic routes, large environmental footprint, complex chemical architecture and time-consuming and purification processes. Continuous flow technology has emerged as a potent and enabling tool in the synthesis of complex natural products because of its efficiency and environmentally benign nature. Herein, we review advances in continuous flow synthesis of diverse natural products with biological activity to demonstrate the impact and potential of the technology in overcoming challenges faced in natural products synthesis. Consequently, this allows for easy and efficient access to atypical or structurally complex natural products. Overall, this article highlights the transformative impact of continuous flow technology on the bioactive natural products synthesis and offer a useful reference tool for chemists interested in the synthesis of these compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134333"},"PeriodicalIF":2.1,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533894","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

Recognition of carboxylic acids and phosphonic acids using a 1,8-diphenylanthracene-based diguanidine in solution and solid states

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-24 DOI: 10.1016/j.tet.2024.134314

Takahiro Kusukawa, Masashi Ooe, Kensuke Inuzuka

{"title":"Recognition of carboxylic acids and phosphonic acids using a 1,8-diphenylanthracene-based diguanidine in solution and solid states","authors":"Takahiro Kusukawa, Masashi Ooe, Kensuke Inuzuka","doi":"10.1016/j.tet.2024.134314","DOIUrl":"10.1016/j.tet.2024.134314","url":null,"abstract":"<div><div>A 1,8-diphenylanthracene-based diguanidine <strong>1</strong> has been designed and synthesized for the recognition of carboxylic acids and phosphonic acid derivatives. The diguanidine <strong>1a</strong> forms 1:1 complexes with the dicarboxylic acids and the diphosphonic acid derivatives in a DMSO solution, and the formation of these complexes was confirmed by a DOSY NMR analysis. The binding mode towards the guanidyl group (Type I, Type II, two existing types of binding modes toward three nitrogen atoms) with a diphosphonic acid derivative was successfully demonstrated by the 2D NOESY analysis. The diguanidine <strong>1a</strong> does not show any fluorescence in a DMSO solution, but after the addition of carboxylic acids, the formation of a stable complex or the formation of the protonated guanidinium (<strong>1a</strong>+2H<sup>+</sup>) were distinguishable by the observation of a light-blue fluorescence around 430 nm. These fluorescence observations can be determined the stability of the complexes of the diguanidine <strong>1a</strong> with carboxylic acids. On the other hand, the DMSO solution of diguanidine <strong>1a</strong> showed a light-blue fluorescence after the addition of phosphonic acids. Interestingly, diguanidine <strong>1a</strong> recognized methylphosphonic acid <strong>9a</strong> in the solid state by grinding and showed a green fluorescence, while the other phosphonic acids <strong>9</strong> and dicarboxylic acids (<strong>4d</strong>: pimelic acid, <strong>4f</strong>: azelaic acid) showed a light-blue fluorescence in the solid state, and a selectivity was observed. These fluorescence characteristics of the diguanidine <strong>1</strong> are applicable for the detection of carboxylic acids and phosphonic acids, especially for methylphosphonic acid <strong>9a</strong> in the solid state.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134314"},"PeriodicalIF":2.1,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743630","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

Regioselective C(sp2)-H nitrosation and nitration of (Hetero)arenes with Fe(NO3)3·9H2O as promoter, nitroso and nitro source 以Fe(NO3)3-9H2O为促进剂、亚硝基和硝基源的（异）烷的区域选择性C(sp2)-H亚硝化和硝化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-23 DOI: 10.1016/j.tet.2024.134329

Ailong Shao, Yuanyuan Li, Min Dong, Yuhang Wang, Rongjing Zhao, Jun Zhang, Shuisheng Chen, Hai Wu

引用次数: 0

Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles 噁唑硼烷催化二芳基膦氧化物与 α、β-不饱和 N-酰基吲哚和 N-酰基吡咯的不对称 1,4-加成反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-23 DOI: 10.1016/j.tet.2024.134331

Jinyi Qian, Wendi Shao, Qi Gao, Jiuling Li, Baomin Fan, Yafei Guo

引用次数: 0

Dithiolation of [60]fullerene with aliphatic primary thiols initiated by n-butylamine via aerobic oxidation reaction 正丁胺通过有氧氧化反应引发[60]富勒烯与脂肪族伯硫醇的二硫化反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-22 DOI: 10.1016/j.tet.2024.134313

Sheng-Li Wu , Yu-Bo Li , Song-Xiao Yu , Peiwen Lv , Jintao Guan , Yi Wang , Zong-Jun Li

引用次数: 0

Amide synthesis from DDQ-mediated electrochemical Beckmann rearrangement 通过 DDQ 介导的电化学贝克曼重排合成酰胺

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-22 DOI: 10.1016/j.tet.2024.134324

Ren-Yu Tian , Mohammad Sanayi Haqmal , Yu-Ting Bao , Shi-Yao Liu , Guang-Ying Chen , Li Tang

引用次数: 0

Synthesis of novel isostere analogues of naphthyridines using CuI catalyst: DFT computations (FMO, MEP), molecular docking and ADME analysis 使用 CuI 催化剂合成新型萘啶类等效类似物：DFT 计算（FMO、MEP）、分子对接和 ADME 分析

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-10-22 DOI: 10.1016/j.tet.2024.134323

Kolandaivel Prabha , Satheeshkumar Rajendran , Balasubramanian Mythili Gnanamangai , Balachandra Mohan J , Koray Sayin , K.J. Rajendra Prasad , Gamze Tüzün

{"title":"Synthesis of novel isostere analogues of naphthyridines using CuI catalyst: DFT computations (FMO, MEP), molecular docking and ADME analysis","authors":"Kolandaivel Prabha , Satheeshkumar Rajendran , Balasubramanian Mythili Gnanamangai , Balachandra Mohan J , Koray Sayin , K.J. Rajendra Prasad , Gamze Tüzün","doi":"10.1016/j.tet.2024.134323","DOIUrl":"10.1016/j.tet.2024.134323","url":null,"abstract":"<div><div>An approach towards the synthesis of novel isosteres of benzonaphthyridines and benzonaphthonaphthyridines from the condensation reaction between 4-chloro-2-methylquinolines/4-chloro-2-methylbenzo[<em>h</em>]quinoline and appropriate <em>o</em>-amino aromatic and heteroaromatic carboxylic acids by using solvent (ethanol)/solvent free (neat) condition to yield the intermediate followed by the cyclization with PPA. The intermediate yield has been slightly increased in neat (solvent-free) conditions compared to solvent conditions. Further, the target isosteres of benzonaphthyridines and benzonaphthonaphthyridines were achieved in the one-pot synthesis using a CuI catalyst with a higher yield than the stepwise method. Quantum chemical calculations of synthesized compounds are performed by using M06-2X with 6-311+G(d,p) basis set in water, DFT calculations of the molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs), and the optimized geometry of the XRD values are compared with experimental values. All the synthesized novel isosteres molecules are investigated under molecular docking studies using MMP1 and MMP2 proteins, which showed all the molecules have the potential to heal pancreatic cancer. The most potent molecules among them are <strong>3i</strong> and <strong>3h</strong> due to their better docking scores. Furthermore, the molecules' pharmacokinetic (ADME) parameters have been observed to be effective in future biological evaluations of these compounds to be active.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134323"},"PeriodicalIF":2.1,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533895","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