Asian Journal of Organic Chemistry最新文献

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Synthesis of a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400637

Ruijun Jiang , Tingting Qin , Yiping Wang , Huicong Cui , Yanping Shi , Lei Zhang , Dr. Xuguang Liu

Ullazine, a typical polycyclic aromatic hydrocarbon with a 14 π‐electron nitrogen‐containing core, has garnered significant attention due to its excellent performance in optoelectronics applications. Integration of heteroatoms into the frameworks of polycyclic aromatic hydrocarbons is a well‐established strategy for modifying molecular characteristics and functionalities. In this study, heteroatom‐doped ullazine congener Bis‐BS‐U containing two boron‐sulfur bonds was synthesized. The structures and properties of Bis‐BS‐U were systematically compared to those of the previously reported bis‐boron/nitrogen doped ullazine (Bis‐BN‐U) and bis‐boron/oxygen doped ullazine (Bis‐BO‐U). Notably, the absorption and fluorescence spectra of Bis‐BS‐U exhibited a pronounced red shift relative to those of Bis‐BN‐U and Bis‐BO‐U. Theoretical calculations suggest that the boron/sulfur six‐member ring in Bis‐BS‐U exhibits very weak antiaromaticity. Moreover, the fluorescence intensity of Bis‐BS‐U showed an initial increase upon addition of Hg²⁺, followed by gradual decrease over time. This study expands the family of ullazine and provides valuable insights for the future development of heteroatom‐doped ullazines.

{"title":"Synthesis of a Bis‐Boron/Sulfur Doped Ullazine and Direct Comparison with Its Boron/Nitrogen and Boron/Oxygen Analogues","authors":"Ruijun Jiang , Tingting Qin , Yiping Wang , Huicong Cui , Yanping Shi , Lei Zhang , Dr. Xuguang Liu","doi":"10.1002/ajoc.202400637","DOIUrl":"10.1002/ajoc.202400637","url":null,"abstract":"<div><div>Ullazine, a typical polycyclic aromatic hydrocarbon with a 14 π‐electron nitrogen‐containing core, has garnered significant attention due to its excellent performance in optoelectronics applications. Integration of heteroatoms into the frameworks of polycyclic aromatic hydrocarbons is a well‐established strategy for modifying molecular characteristics and functionalities. In this study, heteroatom‐doped ullazine congener <strong>Bis‐BS‐U</strong> containing two boron‐sulfur bonds was synthesized. The structures and properties of <strong>Bis‐BS‐U</strong> were systematically compared to those of the previously reported bis‐boron/nitrogen doped ullazine (<strong>Bis‐BN‐U</strong>) and bis‐boron/oxygen doped ullazine (<strong>Bis‐BO‐U</strong>). Notably, the absorption and fluorescence spectra of <strong>Bis‐BS‐U</strong> exhibited a pronounced red shift relative to those of <strong>Bis‐BN‐U</strong> and <strong>Bis‐BO‐U</strong>. Theoretical calculations suggest that the boron/sulfur six‐member ring in <strong>Bis‐BS‐U</strong> exhibits very weak antiaromaticity. Moreover, the fluorescence intensity of <strong>Bis‐BS‐U</strong> showed an initial increase upon addition of Hg<sup>2+</sup>, followed by gradual decrease over time. This study expands the family of ullazine and provides valuable insights for the future development of heteroatom‐doped ullazines.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400637"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622449","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 of Polysubstituted Indoles via the Indium‐Promoted Regioselective Hydrohydrazination of Terminal Alkynes

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400682

Norio Sakai , Takahiro Yokoyama , Kento Ishida

We demonstrated that indium bromide, a trivalent indium compound with strong tolerance toward various coordination functional groups, can be used as a sole promotor to effectively promote the hydrohydrazination of a variety of N‐phenylhydrazines with aromatic/aliphatic alkynes and the subsequent [3,3]‐sigmatropic reaction of the hydrazone intermediate, leading to the one‐pot preparation of various poly‐substituted indole derivatives. Notably, the initial hydrohydrazination proceeded in a Markovnikov‐type manner and showed high regioselectivity, with the hydrohydrazination of arylalkynes affording only 2‐arylindole derivatives. Therefore, our findings provide a facile and practical one‐pot process for the synthesis of polysubstituted indole derivatives from various phenylhydrazines and aromatic/aliphatic alkynes using only one promotor.

引用次数: 0

C–Centered Radicals: Generation, Detection, Stability and Perspectives

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400686

Dr. Archana Velloth , Piyush Kumar , Shabana Butt , Dr. Sugumar Venkataramani

C–Centered radicals are one of the classical reactive intermediates that have shown enormous utility in organic synthesis. Besides homolytic bond cleavages, the advancements of electron transfer‐based photoredox and electroredox processes are popular choices for their generation and synthetic explorations. Considering the widespread attention and versatility of C‐centered radicals in several fields, a systematic understanding of structural, stability, and reactivity aspects is crucial for the further development and futuristic applications of radical chemistry. In this regard, several topics pertaining to the generation, detection, and studies relevant to radical chemistry in general and thermodynamic and kinetic stability of the C‐centered radicals specifically, with a major emphasis on physical organic chemistry aspects, are presented. Besides portraying the factors governing their stability and reactivity, this contribution also discusses their challenges and perspectives.

引用次数: 0

Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400617

Fatemeh Doraghi , Shahab Kermaninia , Hadi Afaridoun , Bagher Larijani , Mohammad Mahdavi

Transition metal‐catalyzed transformations of bridged‐ring bicyclic alkenes have emerged as an interesting area of synthetic chemistry in the last two decades. Due to their multiple points of reactivity, bicyclic alkenes, especially oxa/aza‐bicyclic alkenes, can participate in a variety annulation/functionalization reactions catalyzed by transition metals. In this review, a wide range of transition metal‐catalyzed C−H activation/addition of bicyclic alkenes with nucleophiles is described.

近二十年来，过渡金属催化的桥环双环烯转化已成为合成化学的一个有趣领域。由于双环烯，尤其是氧杂/氮杂双环烯具有多点反应活性，因此可以在过渡金属催化下参与各种环化/官能化反应。在本综述中，介绍了一系列过渡金属催化的双环烯与亲核物的 C-H 活化/加成反应。

引用次数: 0

A Review on Use of Electrolytes in Catalytic/ Sub‐Stoichiometric Amounts in Electro‐Organic Synthesis: A Much Greener Approach

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400307

Dr. Toreshettahally R. Swaroop , Dr. Rajaghatta N. Suresh , Dr. Muddegowda Umashankara , Dr. Kanchugarakoppal S. Rangappa

In this review, we have discussed the various types of organic electrochemical reactions which use catalytic/sub‐stoichiometric amount of inorganic and/or organic salts as electrolytes. We have also presented the plausible mechanism of each electro‐organic reaction. This review article highlights notable examples of electro‐organic synthesis published from 2000 to 2023.

引用次数: 0

Synthesis of 2H‐1,4‐Oxazin‐3(4H)‐One Utilizing Umpolung Reaction to α‐Hydrazonoketone

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400698

Dr. Isao Mizota , Keiji Oshima , Nozomi Hoshiai , Ayaki Yamamoto , Masaki Mitani , Rabbia Batool , Prof. Dr. Bo‐Tau Liu , Prof. Dr. Makoto Shimizu

2H‐1,4‐Oxazin‐3(4H)‐One Derivatives Are Known to Exhibit a Wide Range of Biological Activities Such as Antifungal, Anticancer, as Receptor Antagonists and Potassium Channel Modulators. In This Report, We Describe That α‐Hydrazonoketone Is an Appropriate Substrate for the Umpolung Reaction and a Promising Candidate for the Synthesis of 2H‐1,4‐Oxazine‐3(4H)‐Ones. Notably, Umpolung N‐Methylation for α‐Hydrazonoketone Proceeded Quantitatively in a Mild and Extremely Short Reaction Time, Which Has Been Difficult to Achieve in the Conventional Reactions. Moreover, We Also Developed Tandem Umpolung Reaction/Reduction/N‐Acyl‐O‐Alkylation to Afford 2H‐1,4‐Oxazin‐3(4H)‐Ones in High Yield in the Presence of Chloroacetyl Chloride.

引用次数: 0

Oxirane‐Driven Cascade Transformations of 5‐Arylidene‐Thiazolidine‐2,4‐Diones

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400645

Dr. Alexander Yu. Simonov , Dr. Alexey A. Panov , Dr. Andrei V. Churakov , Prof. Dr. Vladimir I. Polshakov , Prof. Dr. Igor B. Levshin

The reaction of thiazolidine‐2,4‐diones (TZDs) with oxiranes has been thoroughly investigated. For the first time, it has been observed that 5‐arylidene‐TZD derivatives can undergo transformation into 6‐substituted 1,4‐oxathian‐2‐ones. Additionally, it has been demonstrated that certain 3‐substituted 5‐arylidene‐TZDs can convert to 1,4‐oxathian‐2‐ones and oxazolidines upon reaction with oxiranes, confirming that the process follows a cascade mechanism. Several factors have been found to influence the reaction‘s outcome, including the amount of oxirane, the presence of a base, and solvent polarity. It has been determined that dimethylformamide (DMF) is essential for the reaction to proceed efficiently. Furthermore, the critical role of the benzylidene group in facilitating the reaction has been confirmed. An unusual hydrogen bond between the ortho‐hydrogens of the phenyl group and the sulfur atom of the thiazolidine ring, observed via NMR spectroscopy, highlights the sulfur atom‘s strong electron‐accepting properties, which play a key role in the observed transformations.

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引用次数: 0

Synthesis of Bridged and Fused Tetracycles via Rhodium‐Catalyzed C−H Allylation/Cycloaddition of Azomethine Imines with MBH Adducts and Allyl Acetates

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400646

Yang Sun , Yiyan Wang , Lijun Zhang , Rui Zhong , Hui Wang

A rhodium‐catalyzed cascade C−H allylation combined with exo‐ and endo‐type [3+2] dipolar cycloaddition of aryl azomethine imines with Morita‐Baylis‐Hillman (MBH) adducts and allyl acetates is described. This process, which is operationally simple and proceeds efficiently in air and moisture under neat conditions, facilitates diverse bridged and fused tetracycles as single diastereomers. The reaction showcases a broad substrate scope and good functional group compatibility. Furthermore, its practicality is further demonstrated through successful scale‐up and synthetic applications.

引用次数: 0

Pyridinium‐Based Schiff‐Base Fluorescent Chemosensor for Sequential Detection of Al3+ Ions and TNP: Applications in Cell Imaging and Latent Fingerprint Visualization

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400669

Pragya , Sonali J. Jain , Krishnan Rangan , Prabhat Nath Jha , Bharti Khungar

A fluorescent pyridinium‐based chemosensor (E)‐1‐(2‐(3‐hydroxy‐4‐((pyridin‐2‐ylimino) methyl) phenoxy) ethyl) pyridin‐1‐ium bromide (BzPySB) was synthesized and characterized using various spectroscopic techniques. The chemosensing potential of BzPySB was explored using UV‐vis and fluorescence spectroscopy in the aqueous medium. The turn‐on fluorescence behavior was observed for BzPySB in the presence of Al³⁺, while other metal ions were non‐responsive. The B−H and Job′s plot confirmed the 1 : 1 stoichiometric ratio of the BzPySB and Al³⁺. The in situ generated complex BzPySB‐Al³⁺ offered selectivity toward TNP via fluorescence turn‐off phenomena with high K_sv and LOD values. The “off‐on‐off” sensing mechanism was elucidated through ¹H NMR, mass spectrometry, and DFT calculations. The probe also detected Al³⁺ in plant and MCF‐7 cells, highlighting its potential in biological systems. Moreover, BzPySB exhibited solid‐state luminescent properties credited to weak π‐π interaction, leading to its successful application in the visualization of latent fingerprints.

本研究合成了一种基于吡啶的荧光化学传感器（E）-1-(2-(3-羟基-4-((吡啶-2-亚氨基)甲基)苯氧基)乙基)吡啶-1-鎓溴化物（BzPySB），并利用各种光谱技术对其进行了表征。在水介质中使用紫外可见光谱和荧光光谱探索了 BzPySB 的化学传感潜力。观察到 BzPySB 在 Al3+ 存在下的荧光开启行为，而其他金属离子则无反应。B-H 图和 Job′s 图证实了 BzPySB 和 Al3+ 的化学计量比为 1 ：1 的化学计量比。原位生成的 BzPySB-Al3+ 复合物通过荧光熄灭现象对 TNP 具有选择性，具有较高的 Ksv 值和 LOD 值。通过 1H NMR、质谱分析和 DFT 计算，阐明了 "off-on-off "传感机制。该探针还能在植物和 MCF-7 细胞中检测到 Al3+，突显了其在生物系统中的应用潜力。此外，由于 BzPySB 具有微弱的 π-π 相互作用，因此它具有固态发光特性，从而成功地应用于潜在指纹的可视化。

{"title":"Pyridinium‐Based Schiff‐Base Fluorescent Chemosensor for Sequential Detection of Al3+ Ions and TNP: Applications in Cell Imaging and Latent Fingerprint Visualization","authors":"Pragya , Sonali J. Jain , Krishnan Rangan , Prabhat Nath Jha , Bharti Khungar","doi":"10.1002/ajoc.202400669","DOIUrl":"10.1002/ajoc.202400669","url":null,"abstract":"<div><div>A fluorescent pyridinium‐based chemosensor (E)‐1‐(2‐(3‐hydroxy‐4‐((pyridin‐2‐ylimino) methyl) phenoxy) ethyl) pyridin‐1‐ium bromide (<strong>BzPySB</strong>) was synthesized and characterized using various spectroscopic techniques. The chemosensing potential of <strong>BzPySB</strong> was explored using UV‐vis and fluorescence spectroscopy in the aqueous medium. The turn‐on fluorescence behavior was observed for <strong>BzPySB</strong> in the presence of Al<sup>3+</sup>, while other metal ions were non‐responsive. The B−H and Job′s plot confirmed the 1 : 1 stoichiometric ratio of the <strong>BzPySB</strong> and Al<sup>3+</sup>. The in situ generated complex <strong>BzPySB</strong>‐Al<sup>3+</sup> offered selectivity toward TNP via fluorescence turn‐off phenomena with high <em>K</em><sub>sv</sub> and LOD values. The “off‐on‐off” sensing mechanism was elucidated through <sup>1</sup>H NMR, mass spectrometry, and DFT calculations. The probe also detected Al<sup>3+</sup> in plant and MCF‐7 cells, highlighting its potential in biological systems. Moreover, <strong>BzPySB</strong> exhibited solid‐state luminescent properties credited to weak <em>π‐π</em> interaction, leading to its successful application in the visualization of latent fingerprints.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400669"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622492","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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

Deacylation of N‐Acylsulfonamides Mediated by Metal Triflimides

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry

Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400673

Juan Tian , Shimin Yang , Ying Peng , Mengyun Chen , Xin Chen , Xinyi Wang , Dayong Sang

N‐Acylsulfonamides play a significant role in organic and medicinal chemistry. The N‐deacylation of N‐acylsulfonamides is an important transformation that releases the sulfonamide structural motif. Herein, a metal triflimide‐catalyzed nonhydrolytic method for the deacylation of N‐acylsulfonamides is presented. Commercially available metal triflimides reactive for the N‐deacylation include Cu(NTf₂)₂, Zn(NTf₂)₂, Mg(NTf₂)₂, Ce(NTf₂)₃, and La(NTf₂)₃. A range of N‐acyl groups, including acetyl, propionyl, butyryl, isobutyryl, octanoyl, benzoyl, 2‐phenylacetyl, and sterically hindered pivaloyl are readily deblocked efficiently. A variety of functional groups, such as halogeno, keto, nitro, cyano, ether, and carboxylate, are tolerated intact.

引用次数: 0

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