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One pot synthesis of 4-iodo-3-phenylbenzo[b][1,6]naphthyridine via imino iodization-cyclization of alkynylquinoline-3-carbaldehydes 通过炔基喹啉-3-羰基醛的亚氨基碘化-环化一次性合成 4-碘-3-苯基苯并[b][1,6]萘啶
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-12 DOI: 10.1080/00397911.2024.2389542
Rashmi Singh , Vishal Prasad Sharma , Rajesh Kumar , Manish Raj , Tanu Gupta

Simple, environmentally benign and metal free one pot strategy has been used for the synthesis of 4-iodo-3-phenylbenzo[b][1,6]naphthyridine from O-alkynylquinolinyl aldehydes with tert-butyl amine and iodine through imine formation in good to excellent yield at room temperature in aerobic and mild conditions. The beauty of this reaction is the imine formation and cyclization in the same reaction pot. Due to presence of iodine in product, it can be useful for further reaction and can be valuable synthon for new organic compounds.

在室温、有氧和温和的条件下,采用简单、环保和无金属的一锅法从 O-炔基喹啉基醛与叔丁胺和碘通过亚胺的形成合成了 4-碘-3-苯基苯并[b][1,6]萘啶,收率良好甚至极佳。该反应的美妙之处在于亚胺的形成和环化在同一反应釜中完成。由于产物中含有碘,它可用于进一步反应,并可作为新有机化合物的重要合成物。
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引用次数: 0
Synthesis of trifluoromethyl substituted heterocyclic compounds with β-trifluoromethylated acrylates 用 β-三氟甲基丙烯酸酯合成三氟甲基取代的杂环化合物
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-10 DOI: 10.1080/00397911.2024.2390696
Cai Zhang
Trifluoromethyl heterocyclic compounds have high lipophilicity, metabolic stability and binding selectivity, so it is very important to develop their synthetic methods. This review provides an overview of synthesis of trifluoromethyl substituted heterocyclic compounds from β-trifluoromethylated acrylates over the period from 2018 to the present.
三氟甲基杂环化合物具有很高的亲脂性、代谢稳定性和结合选择性,因此开发其合成方法非常重要。本综述介绍了...
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引用次数: 0
Synthesis, antiproliferative activity and insilco studies of substituted 2-((N-benzyl-5-bromo-2-methoxyphenyl) sulfonamide) glycinamide derivatives 取代的 2-((N-苄基-5-溴-2-甲氧基苯基)磺酰胺)甘氨酰胺衍生物的合成、抗增殖活性和绝缘研究
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-06 DOI: 10.1080/00397911.2024.2387810
Dattatray D. Gaikwad , Sachin A. Dhawale , Chandrakant D. Pawar , Dattatraya N. Pansare , Umakant D. Pawar , Ashok M. Zine

The present work aimed to synthesize different substituted glycinamide derivatives. A series of novel substituted 2-((N-benzyl-5-bromo-2-methoxyphenyl) sulfonamide) and their glycinamide derivatives (5a–5p) were synthesized. We developed a simple strategy for synthesizing functionally diverse sulfonamide and glycinamide derivatives through a series of steps. A series of molecules containing amide derivatives were designed and synthesized, and their structures were elucidated and confirmed by1H NMR, 13 C NMR, LCMS, and their purity was checked using HPLC. The synthesized compounds were screened for anticancer activity against A-549 and A431 cancer cell lines by MTT assay and then docking studies were carried out to understand the molecular interactions. The preliminary bioassay suggests that most compounds showed remarkable anti-proliferation activity. Gefitinib was used as a positive control. The compounds 5g and 5f were active compared with Gefitinib in both the cell lines.

本研究旨在合成不同的取代甘氨酰胺衍生物。我们合成了一系列新型取代的 2-((N-苄基-5-溴-2-甲氧基苯基)磺酰胺)及其甘氨酰胺衍生物(5a-5p)。我们开发了一种简单的策略,通过一系列步骤合成功能多样的磺酰胺和甘氨酰胺衍生物。我们设计并合成了一系列含有酰胺衍生物的分子,并通过 1H NMR、13 C NMR 和 LCMS 对其结构进行了阐明和确认,同时使用 HPLC 对其纯度进行了检测。通过 MTT 试验筛选了合成的化合物对 A-549 和 A431 癌细胞株的抗癌活性,然后进行了对接研究以了解分子间的相互作用。初步生物测定表明,大多数化合物具有显著的抗癌活性。吉非替尼被用作阳性对照。与吉非替尼相比,化合物 5g 和 5f 在两种细胞系中都具有活性。
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引用次数: 0
Nucleophilic reactions with 3-formylchromones: A decade update 与 3-甲酰基色素的亲核反应:十年更新
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-05 DOI: 10.1080/00397911.2024.2387134
Magdy A Ibrahim , Mohamed Abdel-Megid , Osama Farouk , Nasser M. El-Gohary , Asmaa I Nabeel , Marwa M. A. Attai , Al-Shimaa Badran

The chemical reactivity of 3-formylchromones toward several carbon and nitrogen nucleophiles is collected in this review. Certain annulated chromones and 3-heteroaryl chromones were synthesized. A diversity of three component reactions including 3-formylchromones was also summarized.

本综述收集了 3-甲酰基色酮对几种碳和氮亲核物的化学反应性。本综述收集了 3-甲酰基色原酮与几种碳氮亲核物的化学反应性,并合成了某些环状色原酮和 3-异芳基色原酮。还总结了包括 3-甲酰基色原酮在内的三组分反应的多样性。
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引用次数: 0
TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[b][1,8]naphthyridin derivatives via metal free Cascade annulation TBAB 催化辅助 C-C/C-N 键形成:通过无金属级联环化获得二氢苯并[b][1,8]萘啶衍生物的有效方法
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2379447
Jiming Liu , Xinghua Zheng , Wenjun Luo , Zhengwang Chen , Fei Ling

An eco-friendly, metal-free approach for synthesizing dihydrobenzo[b][1,8]naphthyridine derivatives has been established. This method employs ortho-chloroquinolin-α,β-unsaturated ketones as dipolarophiles and acyclic enaminones as amphiphilic nucleophiles, enabling a formal [3 + 3] annulation reaction under phase-transfer catalysis to offed the targeted products. It boasts transition-metal-free conditions, broad functional group compatibility, and straightforward operational procedures.

合成二氢苯并[b][1,8]萘啶衍生物的环保型无金属方法已经建立。该方法采用正交-氯喹啉-α,β-不饱和酮作为双极性...
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引用次数: 0
1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization 1,4,5,8-四取代二氢蒽基三庚烯三醌:合成、结构和理化特性分析
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2381074
Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An

1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and tris(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and tris(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.

通过 TT 与 1,4,5,8-四(己氧基)蒽之间的 Diels-Alder 反应合成了 1,4,5,8-四取代二氢蒽基三庚烯三醌(TT)分子 THAO-TT 和 tris(THAO)-TT,从而制备出含有电子接受官能团的扩展三庚烯衍生物。制备的 THOA-TT 和三(THOA)-TT 具有良好的热稳定性,这得益于 TT 的刚性框架。THOA-TT 和三(THOA)-TT 的光学和氧化还原特性由苯醌单元和外围单元之间通过连接的甲基进行的同共轭控制。
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引用次数: 0
Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups 带有不同烷基氨基的新型高氟化磷酰胺的合成与表征
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2382784
Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi

Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (RFO)2P(O)NHR (R = CH2CH2CH3, (CH2)3CH3, (CH2)4-CH3, CH(CH3)2, C6H11, CH2CH2-C6H5, CH2-C6H5 or C6H5; RF = CH2CF3, CH2C2F5 or CH2CH2C6F13) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H2O2.This method was chosen out of various literature common methods, which were thoroughly investigated using 31P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (1H,13C,31P, and 19F) NMR, IR, and HRMS techniques.

合成了 17 种新的含烷基氨基的(RFO)2P(O)NHR(R = CH2CH2CH3、(CH2)3CH3、(CH2)4-CH3、CH(CH3)2、C6H11、CH2CH2-C6H5、CH2-C6H5 或 C6H5;RF = CH2CF3、CH2C2F5 或 CH2CH2C6F13)高氟化磷酰胺。这些化合物是以分子碘作为温和的催化剂,在 H2O2 的存在下,通过伯胺与作为磷酸化剂的双(多氟烷基)亚磷酸酯反应而得到的。此外,还研究了不同膦酸盐反应速率的变化,并与之前的研究成果进行了比较。利用多核(1H、13C、31P 和 19F)核磁共振、红外和 HRMS 技术对标题磷酰胺进行了全面表征。
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引用次数: 0
Hantzsch reaction: The important key for pyridine/dihydropyridine synthesis 汉兹奇反应:吡啶/二氢吡啶合成的重要关键
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2377738

Pyridines and its derivatives are an important class of heterocyclic compounds of low molecular weight. They have been used in the treatment of a various diseases like cardiovascular disease, antioxidant, antibacterial, anti-tubercular, anticancer, anticoagulant, etc. In 1882, Arthur Hantzsch reported pyridine derivative synthesis using different aldehydes, 2 molecules β-keto ester and ammonium acetate to give a Hantzsch ester or 1,4-dihydropyridine derivatives. This review article focuses on different protocols for Hantzsch reaction using different catalysts like β-cyclodextrin–polyurethane polymer (β-CDPU), chitosan nanoparticles (NPs), salicylic acid, p-toluenesulfonic acid (p-TSA), alginic acid, Fe-TUD-1, PdRuNi@GO, Ceric Ammonium Nitrate (CAN), sulfate polyborate, etc. for the synthesis of pyridine derivatives.

吡啶及其衍生物是一类重要的低分子量杂环化合物。它们已被用于治疗各种疾病,如心血管疾病、抗氧化剂、抗衰老、抗衰老药物、抗肿瘤药物、抗癌药物、抗衰老药物、抗肿瘤药物、抗病毒药物、抗肿瘤药物、抗...
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引用次数: 0
One-step synthesis of sugar nucleotides under optimized conditions 在优化条件下一步合成糖核苷酸
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2380063
Kota Fujihara , Hatsuo Yamamura , Atsushi Miyagawa

Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield.

糖核苷酸是酶促反应中合成生物活性寡糖的重要底物,然而,通过化学和酶促反应制备糖核苷酸具有挑战性。因此,我们研究了在最佳条件下利用简便的一步反应合成糖核苷酸的方法。通过优化的一步反应合成了七种糖核苷酸,产率为 40-80%,其中 1,2-反式糖苷具有优先性。此外,以克为单位合成 UDP-半乳糖的产率为 46%(578 毫克)。
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引用次数: 0
BF3‧OEt2 promoted synthesis of 9-fluorenlidene appended 2-hydrazinopyridine imines from (phenylethynyl)-fluorene and 2-hydrazinopyridine derivatives BF3‧OEt2 促进从(苯乙炔基)-芴和 2-肼基吡啶衍生物合成 9-亚芴基 2-肼基吡啶亚胺的过程
IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Pub Date : 2024-08-01 DOI: 10.1080/00397911.2024.2385538
Suresh Snoxma Smile , Harichandran Gurusamy , Ponnusamy Shanmugam

Reaction of 9-fluorene propargylic alcohols and substituted-2-hydrazinopyridine using BF3·OEt2 as a Lewis acid catalyst afforded 9-fluorenlidene appended 2-hydrazinopyridine imine derivatives has been developed. The scope of the reaction is demonstrated by selecting a range of fluorene propargylic alcohols and substituted 2-hydrazinopyridine imines. All the synthesized molecules were characterized using various spectroscopic and analytical techniques including 1H NMR,13C NMR, and Mass spectrometry. A plausible reaction mechanism for forming title compounds via propargylic allenyl carbocation is postulated. The synthetic utility of products thus formed is demonstrated by utilizing Suzuki coupling.

以BF3-OEt2为路易斯酸催化剂,使9-芴丙炔醇与取代的2-肼基吡啶反应,得到9-芴亚甲基2-肼基吡啶亚胺衍生物。
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引用次数: 0
期刊
Synthetic Communications
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