Sachin M. Thorat, Dr. Anindita Bhowmick, Dr. Sunderraman Sambasivan, Prof. Dr. Ramakrishna G. Bhat
{"title":"Visible-Light Photoredox Catalyzed Facile Synthesis of 2-Amino-1,3,4-Thiadiazoles from Aldehydes and Thiosemicarbazides","authors":"Sachin M. Thorat, Dr. Anindita Bhowmick, Dr. Sunderraman Sambasivan, Prof. Dr. Ramakrishna G. Bhat","doi":"10.1002/ajoc.202500386","DOIUrl":"10.1002/ajoc.202500386","url":null,"abstract":"<p>A metal-free, visible light mediated protocol has been developed to synthesize 2-amino-1,3,4-thiadiazoles (ATZ) from commercially available aldehydes and thiosemicarbazides. This one-pot strategy has been achieved by the condensation of aldehydes with substituted thiosemicarbazides in presence of 2,4,6-tri(<i>p</i>-tolyl)pyrylium tetrafluoroborate (TPP-TFB) as a photoredox catalyst. Different aldehydes/hetero aldehydes, as well as thiosemicarbazides reacted smoothly under the reaction conditions to afford the 2-amino-1,3,4-thiadiazoles in good to excellent yields. The practicality of the developed protocol has been successfully demonstrated by the facile one-pot synthesis of commercial herbicide <i>Tebuthiuron</i> on a gram scale. A series of control experiments, cyclic voltammetry, and fluorescence studies have been carried out to support the proposed reaction pathway.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057922","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}
{"title":"Reductive N-Alkylation of Amides with Carbonyl Compounds Using Copper(II) Bromide and 1,1,3,3-Tetramethyldisiloxane","authors":"Tomoya Nobuta, Noriyuki Yamagiwa, Yutaka Suto","doi":"10.1002/ajoc.202500496","DOIUrl":"10.1002/ajoc.202500496","url":null,"abstract":"<p>We report a reductive <i>N</i>-alkylation of amides using carbonyl compounds as alkylating agents and 1,1,3,3-tetramethyldisiloxane (TMDS) as the reducing agent with CuBr<sub>2</sub>. The synthesis of secondary amides is essential in organic chemistry, and recently, some reductive <i>N</i>-alkylation of primary amides has been reported; however, previous methods require harsh conditions, such as high temperatures and/or pressures, and substrate compatibility is limited. Our method proceeds under mild reaction conditions and does not require toxic or expensive reagents. A range of substrates, including aromatic, aliphatic, and cinnamyl amides, as well as γ-lactams, afforded the corresponding alkylated amides in moderate to high yields. Notably, aldehydes and ketones can serve as alkylating agents in this transformation.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145058061","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}
Jayshree Nandkumar Solanke, Selvam Vasanth, Marappan Pradeep Kumar, Mamidisetti Vishnuvardhan, Dr. Vasudevan Dhayalan, Dr. Rambabu Dandela
{"title":"Green One-Pot Strategy for the Direct Synthesis of Benzil","authors":"Jayshree Nandkumar Solanke, Selvam Vasanth, Marappan Pradeep Kumar, Mamidisetti Vishnuvardhan, Dr. Vasudevan Dhayalan, Dr. Rambabu Dandela","doi":"10.1002/ajoc.202400568","DOIUrl":"10.1002/ajoc.202400568","url":null,"abstract":"<p>A practical and green methodology has been developed for the direct synthesis of arylated 1,2-diketones from aldehydes utilizing 4 mol% of <i>N</i>-heterocyclic carbenes (NHC) organocatalysts and activated carbon. The design of this method is a one-pot, two-step sequence: NHC-catalyzed benzoin condensation followed by aerobic oxidation in the presence of activated carbon (AC) and molecular O<sub>2,</sub> offering good to high yields, tolerating various functional groups. This method demonstrates a sustainable and eco-friendly protocol for efficiently synthesizing benzil scaffolds from a wide range of aldehydes directly through one-pot conversions. Catalyst loading, solvent screening, and mechanistic experiments were also performed to understand the roles of NHC catalysts and activated charcoal.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057791","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}
{"title":"Synthetic Strategies of Guanine Derivatives for Self-Assembly in Supramolecular Chemistry","authors":"Dr. Mengjia Liu, Dr. Jingwen Wei","doi":"10.1002/ajoc.202500502","DOIUrl":"10.1002/ajoc.202500502","url":null,"abstract":"<p>Guanine analogs are powerful molecular platforms for building functional supramolecular assemblies. Their broad utility stems from an exceptional ability to adopt diverse topologies, self-assembling into discrete G<sub>4</sub>-quartet, G-quadruplexes, and extended ribbon-like structures. This structural flexibility underlies their wide range of functional applications. Significant research has focused on chemically modifying guanine derivatives to improve their performance in both aqueous and organic environments, and to make them responsive to external factors such as ionic strength, pH, light, and temperature. These modifications allow the inherent chemical information of guanine to be translated into programmable, higher-order supramolecular systems. Recent progress has led to exciting advances across fields including supramolecular chemistry and chemical biology. In this review, we highlight these developments and discuss how synthetic modifications and interdisciplinary strategies continue to expand the structural and functional diversity of guanine-based systems.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057913","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}
Dr. Ana Andrijević, Milica Marković, Dr. Milica Selaković, Dr. Nađa Grozdanić, Dr. Tatjana Stanojković, Prof.Dr. Andrea M. Nikolić, Prof.Dr. Igor M. Opsenica
{"title":"Exploiting the Versatile Reactivity of Aryldiazonium Tetrafluoroborate Salts in the Synthesis of New Isochromene-Fused CF3-Substituted Pyrazoles with Anticancer Potential","authors":"Dr. Ana Andrijević, Milica Marković, Dr. Milica Selaković, Dr. Nađa Grozdanić, Dr. Tatjana Stanojković, Prof.Dr. Andrea M. Nikolić, Prof.Dr. Igor M. Opsenica","doi":"10.1002/ajoc.202500315","DOIUrl":"10.1002/ajoc.202500315","url":null,"abstract":"<p>Pyrazoles, and in particular their fluorinated derivatives, are valuable heterocyclic moieties in medicinal chemistry. Our research group recently developed a one-pot, two-step synthesis of pyrazolo[3,4-c]isochromenes, combining two privileged structures into a single hybrid molecule. Based on the preliminary anticancer screening results of these derivatives, herein, we designed a next-generation compound library focused on the derivatization of a specific portion of the 1-(trifluoromethyl)-3,5-dihydroisochromeno[3,4-c]pyrazole scaffold via late-stage functionalization. The diverse reactivity of aryldiazonium tetrafluoroborate salts was leveraged to achieve this and generate a small but varied compound library. The new series was tested for their anticancer properties and selected derivatives demonstrated pro-apoptotic activity in the human cervical carcinoma cell lines HeLa. The obtained results highlight these structures as valid candidates for further biological studies, while the streamlined synthetic route offers a facile approach to further structural analogs.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057924","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}
Kumar Naveen, Nishkant Malkoti, Vishesh Singh Rawat, Prof. Dr. Elumalai Gnanamani
{"title":"Diastereoselective Michael Addition of Non-Functionalized Furanone to Nitroalkenes in Aqueous Condition","authors":"Kumar Naveen, Nishkant Malkoti, Vishesh Singh Rawat, Prof. Dr. Elumalai Gnanamani","doi":"10.1002/ajoc.202500354","DOIUrl":"10.1002/ajoc.202500354","url":null,"abstract":"<p>Selectivity plays a major role in organic chemistry and biological applications. Herein, we present a diastereoselective DMAP-catalyzed Michael addition of furanone (butenolide) to nitroalkenes. Notably, our method does not require the pre-activation of furanone as 2-(trimethylsiloxy)furan and utilizes water: ethanol (1:3) as a solvent. These mild conditions afford the <i>anti</i>-Michael products in up to 82% isolated yield with up to 87:13 dr (diastereomeric ratio). The scope of this reaction extends to various aromatic, heteroaromatic, and aliphatic nitroalkenes. Furthermore, we demonstrate this process on a gram scale and highlight the utility of the obtained Michael adducts for accessing natural product cores.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832613","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}
Zhaoyi Wang, Meijun Chen, Assoc. Prof. Jiaxuan Shen
{"title":"Three-Component Difunctionalization of Alkenes or Cyclopropanes Using 4-Cyanopyridine as Pyridylation Reagents","authors":"Zhaoyi Wang, Meijun Chen, Assoc. Prof. Jiaxuan Shen","doi":"10.1002/ajoc.202500494","DOIUrl":"10.1002/ajoc.202500494","url":null,"abstract":"<p>Pyridine cores are important heterocycles that exist in natural products, pharmaceuticals, and chiral ligands. Recently, radical-based 4-cyanopyridine has an effective approach for the synthesis of complex pyridines. In this review, we provide an overview of the recent development of multicomponent reactions using 4-cyanopyridine as pyridylation reagent for rapidly constructing complex molecules, including pyridine core. We systematically classified the recent literatures in the field based on bonding type, including C─C or C-heteroatom. This review aims to highlight the results of 4-cyanopyridine as a powerful pyridylation reagent for multicomponent reactions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057777","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}
Kancharla Niteesh, Cheng-Yen Chung, Chun-Han Cha, Wei-Zheng Zeng, Naoto Uramaru, Ichiro Arai, Pei-Jane Huang, Prof. Fung Fuh Wong
{"title":"Facile Cascade Synthesis of 6-(Chloromethyl)pyrazolo[3,4-d]pyrimidines from 5-Amino-1H-pyrazole-4-carbaldehydes","authors":"Kancharla Niteesh, Cheng-Yen Chung, Chun-Han Cha, Wei-Zheng Zeng, Naoto Uramaru, Ichiro Arai, Pei-Jane Huang, Prof. Fung Fuh Wong","doi":"10.1002/ajoc.202500556","DOIUrl":"10.1002/ajoc.202500556","url":null,"abstract":"<p>A facile cascade method was developed for synthesis of 6-(halomethyl)pyrazolo[3,4-<i>d</i>]pyrimidines from 5-amino-1<i>H</i>-pyrazole-4-carbaldehydes via amidation and sequential heterocyclization in two steps. This synthetic method allowed to prepare 1,3-disubstituted 6-(halomethyl)pyrazolo[3,4-<i>d</i>]pyrimidines by using series of 5-amino-1<i>H</i>-pyrazole-4-carbaldehydes as the starting materials in presence of the commercially available safety agents, including 2-haloacetyl chloride, trimethylamine, and ammonium hydroxide.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057869","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}
Delio Santalucia, Andrea Francesco Landucci, Nicolò Rossi, Alessandro Mandoli
{"title":"Trimethylenemethane for Everyone: Convenient Preparation of the Nakamura-Yamago 1,3-Dipolar Reagent and an Effective Oxidative Transformation of Ketene Acetals","authors":"Delio Santalucia, Andrea Francesco Landucci, Nicolò Rossi, Alessandro Mandoli","doi":"10.1002/ajoc.202500471","DOIUrl":"10.1002/ajoc.202500471","url":null,"abstract":"<p>A convenient route to the Nakamura-Yamago methylenecyclopropane (MCP) precursor <b>1</b> to oxygen-stabilized, singlet trimethylenemethane (TMM) is reported, which avoids the hurdles of the original preparation procedure. An effective oxidation protocol is also introduced for converting the sensitive ketene acetals (KAs) from 1,3-dipolar cycloaddition of <b>1</b> to electron-poor olefins, into the corresponding α-hydroxyesters. The method, based on the use of dimethyldioxirane (DMDO) in acetone, affords fair to good yields (23–81%) for a number of KAs endowed with ketone, ester, or imide functional groups, as well as additional C─C double bonds. The utility of the protocol is further exemplified by the diastereoselective preparation of the Rokach-Galano-Durand bicyclic lactone <i>rac-</i><b>18</b>, one of the most versatile building-blocks for the synthesis of isoprostanoidic derivatives.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057776","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}
Enrique Francés-Poveda, Abigail Montiel, Oscar A. Douglas-Gallardo, Carmen Moya-López, Genesys L. Mahecha, Mario E. Flores, Felipe de la Cruz-Martínez, Francisca Werlinger, Javier Martínez, Agustín Lara-Sánchez
{"title":"Synthesis of Crosslinked Biopolyesters Catalyzed by Natural Amino Acids","authors":"Enrique Francés-Poveda, Abigail Montiel, Oscar A. Douglas-Gallardo, Carmen Moya-López, Genesys L. Mahecha, Mario E. Flores, Felipe de la Cruz-Martínez, Francisca Werlinger, Javier Martínez, Agustín Lara-Sánchez","doi":"10.1002/ajoc.202500475","DOIUrl":"10.1002/ajoc.202500475","url":null,"abstract":"<p>Epoxidized sunflower oil (ESO), derived from waste sunflower oil (WSO), was copolymerized with various biobased cyclic anhydrides via ring-opening copolymerization (ROCOP) reaction to produce highly crosslinked polyesters. This catalytic synthesis was performed by a metal-free catalyst system formed by natural amino acid (L-glutamic acid) and tetrabutylammonium iodide (TBAI). The resulting bio-polyesters, obtained as jelly-like disks, were thoroughly characterized using multiple techniques such as FT-IR, TGA, and DSC. The presence of a crosslinked network in the biobased polymers was assessed by dynamical mechanical analysis (DMA) and at room temperature the rubbery state of crosslinked materials was observed. These materials demonstrated complete degradability when treated with a 1 M aqueous sodium hydroxide solution. In addition, density functional theory (DFT) calculation was employed to elucidate the polymerization mechanism, focusing on the activation stage of the polymerization process. This study provides valuable insights into the catalytic efficiency and mechanistic details of the polymerization process, highlighting the potential of sustainable, metal-free catalysts for producing degradable biopolyesters.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500475","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145057774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}