Shikha Pandey , Arsala Kamal , Ambuj Kumar Kushwaha , Dr. Sundaram Singh
In the current study, for the first time, N‐phenylazo (triazine) derivatives of 6‐aminouracil compounds were produced at room temperature under catalyst‐free conditions in pyridine using an easy, efficient, and green process. The main advantages of this approach are that it doesn't require a catalyst, is inexpensive, eco‐friendly, non‐toxic, and simple to handle. This technique shows a broad range of substrate compatibility for uracil compounds and diazonium salts.
{"title":"Synthesis of N‐Phenylazo (Triazine) Derivatives of 6‐Aminouracil Using Diazonium Salt Under Catalyst‐Free Condition","authors":"Shikha Pandey , Arsala Kamal , Ambuj Kumar Kushwaha , Dr. Sundaram Singh","doi":"10.1002/ajoc.202400409","DOIUrl":"10.1002/ajoc.202400409","url":null,"abstract":"<div><div>In the current study, for the first time, N‐phenylazo (triazine) derivatives of 6‐aminouracil compounds were produced at room temperature under catalyst‐free conditions in pyridine using an easy, efficient, and green process. The main advantages of this approach are that it doesn't require a catalyst, is inexpensive, eco‐friendly, non‐toxic, and simple to handle. This technique shows a broad range of substrate compatibility for uracil compounds and diazonium salts.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400409"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143116239","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}
A palladium‐catalyzed dehydrogenative cross‐coupling reactions between silanes and oxygen‐containing functional groups (water, alcohols, phenols) to generate the corresponding silanols, monosilane ethers, and disilane ethers directly in moderate to high yields. This strategy does not rely on any additional oxidizing agents or proton reductants. The possible mechanisms for this transformation are also proposed.
{"title":"Palladium‐Catalyzed Dehydrogenation Cross‐Coupling Reactions of Hydrosilanes: Facile Synthesis of Silanols and Silyl Ethers","authors":"Lianji Zhang , Yujuan Wu , Cuiping Wang , Yuhui Zhao , Wanguo Wei , Zhiqiang Zhang","doi":"10.1002/ajoc.202400471","DOIUrl":"10.1002/ajoc.202400471","url":null,"abstract":"<div><div>A palladium‐catalyzed dehydrogenative cross‐coupling reactions between silanes and oxygen‐containing functional groups (water, alcohols, phenols) to generate the corresponding silanols, monosilane ethers, and disilane ethers directly in moderate to high yields. This strategy does not rely on any additional oxidizing agents or proton reductants. The possible mechanisms for this transformation are also proposed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400471"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143117390","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}
Weeds are problematic plant species around the world. Various strategies exist for controlling weeds, but chemical treatment remains the preferred method, particularly when using natural substances. In this research, a crude aqueous‐methanol extract from dried Zanthoxylum limonella fruits was acid‐base partitioned into four fractions: neutral extract (NE), acid extract (AE), basic extract (BE), and aqueous extract (AQ). These fractions were further separated into seventeen subfractions: NEF1 to NEF7, AEF1 to AEF5, and BEF1 to BEF5, which were then tested for herbicidal activity against the growth of Chinese amaranth (Amaranthus tricolor) and barnyard grass (Echinochloa crus‐galli). Active subfractions were isolated via column chromatography and identified using spectroscopic methods, yielding seven active compounds: xanthoxyline (1), tambulin (2), atanine (3), prudomestin (4), skimmianine (5), p‐methoxybenzoic acid (6), and methyl caffeate (7). Compounds 2–7 had not been previously reported in Z. limonella. Xanthoxyline (1) was identified as the most potent botanical herbicide, fully inhibiting seed germination of Chinese amaranth and barnyard grass. This compound also decreased seed imbibition and α‐amylase activity in both species. Molecular docking studies on the α‐amylase enzyme (PDB ID: 1BG9) revealed that the aromatic, hydroxy, and carbonyl groups of xanthoxyline (1) interact with the enzyme's active sites.
{"title":"Bioassay‐Guided Extraction and Isolation of Natural Herbicides from Dried Zanthoxylum limonella Alston Fruits","authors":"Warot Chotpatiwetchkul , Patchanee Charoenying , Montinee Teerarak , Jatuporn Meesin , Nathjanan Jongkon , Nawasit Chotsaeng , Chamroon Laosinwattana","doi":"10.1002/ajoc.202400317","DOIUrl":"10.1002/ajoc.202400317","url":null,"abstract":"<div><div>Weeds are problematic plant species around the world. Various strategies exist for controlling weeds, but chemical treatment remains the preferred method, particularly when using natural substances. In this research, a crude aqueous‐methanol extract from dried <em>Zanthoxylum limonella</em> fruits was acid‐base partitioned into four fractions: neutral extract (NE), acid extract (AE), basic extract (BE), and aqueous extract (AQ). These fractions were further separated into seventeen subfractions: NEF1 to NEF7, AEF1 to AEF5, and BEF1 to BEF5, which were then tested for herbicidal activity against the growth of Chinese amaranth (<em>Amaranthus tricolor</em>) and barnyard grass (<em>Echinochloa crus‐galli</em>). Active subfractions were isolated via column chromatography and identified using spectroscopic methods, yielding seven active compounds: xanthoxyline (<strong>1</strong>), tambulin (<strong>2</strong>), atanine (<strong>3</strong>), prudomestin (<strong>4</strong>), skimmianine (<strong>5</strong>), <em>p</em>‐methoxybenzoic acid (<strong>6</strong>), and methyl caffeate (<strong>7</strong>). Compounds <strong>2–7</strong> had not been previously reported in <em>Z. limonella</em>. Xanthoxyline (<strong>1</strong>) was identified as the most potent botanical herbicide, fully inhibiting seed germination of Chinese amaranth and barnyard grass. This compound also decreased seed imbibition and α‐amylase activity in both species. Molecular docking studies on the α‐amylase enzyme (PDB ID: 1BG9) revealed that the aromatic, hydroxy, and carbonyl groups of xanthoxyline (<strong>1</strong>) interact with the enzyme's active sites.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400317"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119175","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}
In article number e202400547, Tomoya Takao, Atsushi Kawamura, and Hidefumi Makabe accomplished the first total synthesis of inaoside A, isolated from the edible mushroom Laetiporus cremeiporus, using α-selective Schmidt glycosylation of the easily prepared 2,3,5-tri-TBS-protected ribofuranosyl trichloroacetimidate as a key step. In this cover picture, the creatures of L. cremeiours are trying to build inaoside by guiding the aglycon to the α-face of the ribose derivative.
{"title":"Front Cover: First Total Synthesis of Inaoside A (Asian J. Org. Chem. 12/2024)","authors":"Tomoya Takao, Atsushi Kawamura, Hidefumi Makabe","doi":"10.1002/ajoc.202481201","DOIUrl":"https://doi.org/10.1002/ajoc.202481201","url":null,"abstract":"<p>In article number e202400547, Tomoya Takao, Atsushi Kawamura, and Hidefumi Makabe accomplished the first total synthesis of inaoside A, isolated from the edible mushroom <i>Laetiporus cremeiporus</i>, using α-selective Schmidt glycosylation of the easily prepared 2,3,5-tri-TBS-protected ribofuranosyl trichloroacetimidate as a key step. In this cover picture, the creatures of <i>L. cremeiours</i> are trying to build inaoside by guiding the aglycon to the α-face of the ribose derivative.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202481201","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142861224","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}
The natural product quinine has been known to humankind for centuries, and in that time has played a pivotal role in the treatment of malaria. Quinine, and the related cinchona alkaloids, have seen widespread contemporary use across chemical and biological disciplines, owing in part to the plethora of functional groups and stereochemical information contained within their scaffold. This review focuses on site‐selective synthetic modifications of the cinchona alkaloids. Our comparative analysis may act as a ‘user manual’ for the selective functionalisation of the cinchona alkaloids, and aims to promote consideration of remarkable and lesser‐understood aspects of cinchona chemistry.
{"title":"Site‐Selective Synthetic Modifications of the Cinchona Alkaloids","authors":"Finlay P. Player , Daniel J. Foley","doi":"10.1002/ajoc.202400397","DOIUrl":"10.1002/ajoc.202400397","url":null,"abstract":"<div><div>The natural product quinine has been known to humankind for centuries, and in that time has played a pivotal role in the treatment of malaria. Quinine, and the related cinchona alkaloids, have seen widespread contemporary use across chemical and biological disciplines, owing in part to the plethora of functional groups and stereochemical information contained within their scaffold. This review focuses on site‐selective synthetic modifications of the cinchona alkaloids. Our comparative analysis may act as a ‘user manual’ for the selective functionalisation of the cinchona alkaloids, and aims to promote consideration of remarkable and lesser‐understood aspects of cinchona chemistry.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400397"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860655","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}
Herein an efficient method for in situ generated o–quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The in situ generated o–quinone methides could be undergoing conjugate addition with 3‐aryl oxindoles in one‐pot reaction system, which provided 3,3‐disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).
{"title":"Conjugate Addition of 3‐Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups","authors":"Liu Song","doi":"10.1002/ajoc.202400370","DOIUrl":"10.1002/ajoc.202400370","url":null,"abstract":"<div><div>Herein an efficient method for <em>in situ</em> generated <em>o</em>–quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The <em>in situ</em> generated <em>o</em>–quinone methides could be undergoing conjugate addition with 3‐aryl oxindoles in one‐pot reaction system, which provided 3,3‐disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400370"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860748","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}
Microwave synthesis is a sustainable and eco‐friendly method for producing novel organic compounds, offering faster reactions, higher yields, and improved purity compared to traditional techniques. Efficiency is increased by the uniform heating caused by microwave radiation, especially for the synthesis of heterocyclic compound and their derivatives. Owing to have important biological and therapeutic qualities, a number of microwave‐assisted synthetic methods of pyrroles have been developed that produce better results than the conventional reported method. In view of this, the present review emphasizes solvent‐free and catalyst‐free methods for the microwave‐assisted synthesis of pyrrole and its fusion with other heterocycles such as furan, pyridine, beta‐lactam, and indole. A comparison between traditional and microwave‐assisted techniques is given in terms of reagents, covering yield, waste minimization, solvents, and catalysts.
{"title":"Microwave‐Assisted Synthetic Pathways of Pyrrole: A Comprehensive Review","authors":"Ritika Yadav , Mohit Sanduja , Vinod Kumar , Kirti Sharma , Sameer Khan , Kapil Kumar","doi":"10.1002/ajoc.202400401","DOIUrl":"10.1002/ajoc.202400401","url":null,"abstract":"<div><div>Microwave synthesis is a sustainable and eco‐friendly method for producing novel organic compounds, offering faster reactions, higher yields, and improved purity compared to traditional techniques. Efficiency is increased by the uniform heating caused by microwave radiation, especially for the synthesis of heterocyclic compound and their derivatives. Owing to have important biological and therapeutic qualities, a number of microwave‐assisted synthetic methods of pyrroles have been developed that produce better results than the conventional reported method. In view of this, the present review emphasizes solvent‐free and catalyst‐free methods for the microwave‐assisted synthesis of pyrrole and its fusion with other heterocycles such as furan, pyridine, beta‐lactam, and indole. A comparison between traditional and microwave‐assisted techniques is given in terms of reagents, covering yield, waste minimization, solvents, and catalysts.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400401"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142861165","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}
Arunava Misra , Sudipta Mondal , Mohabul Alam Mondal
Ortho‐Phthaldehyde (OPA) is one of the isomers of benzenedicarbaldehydes. It exhibits distinctive chemical properties stemming from the closely attached dicarbaldehyde groups. Since its development, it has been widely employed as a potent disinfectant, owing to its inherent antimicrobial properties. OPA has the ability to form a fluorescent product with primary amines, making it useful for detecting and estimating various biogenic amines, peptides, and proteins in bodily fluids. Moreover, the combination of thiol and amine with OPA produces a more sensitive fluorogenic compound, significantly enhancing the sensitivity and specificity of OPA‐based analytical techniques. This review summarizes recent developments in biochemical analysis using OPA. It also discusses key achievements in the development of photoactive polymers. Additionally, it covers the use of OPA as a synthetic precursor to achieve small molecules with unique structures that have become increasingly important in various fields of scientific research from 2004.
{"title":"O‐Phthalaldehyde: A Versatile Chemical with its Roles and Future Perspectives","authors":"Arunava Misra , Sudipta Mondal , Mohabul Alam Mondal","doi":"10.1002/ajoc.202400383","DOIUrl":"10.1002/ajoc.202400383","url":null,"abstract":"<div><div><em>Ortho</em>‐Phthaldehyde (OPA) is one of the isomers of benzenedicarbaldehydes. It exhibits distinctive chemical properties stemming from the closely attached dicarbaldehyde groups. Since its development, it has been widely employed as a potent disinfectant, owing to its inherent antimicrobial properties. OPA has the ability to form a fluorescent product with primary amines, making it useful for detecting and estimating various biogenic amines, peptides, and proteins in bodily fluids. Moreover, the combination of thiol and amine with OPA produces a more sensitive fluorogenic compound, significantly enhancing the sensitivity and specificity of OPA‐based analytical techniques. This review summarizes recent developments in biochemical analysis using OPA. It also discusses key achievements in the development of photoactive polymers. Additionally, it covers the use of OPA as a synthetic precursor to achieve small molecules with unique structures that have become increasingly important in various fields of scientific research from 2004.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400383"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862096","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}
Nanfang Wang , Wozheng Fang , Yu Yan , Nan Sun , Junbiao Chang , Xiao‐Na Wang
A TMSOTf‐catalyzed annulation was developed for the construction of polysubstituted maleimides from ynamides and alkynyl sulfoxides, using oxygen as a green oxidant and ynamides as both carbon and nitrogen sources. This novel protocol proceeds in the presence of TMSOTf without the need for an expensive catalytic system and tolerates a broad substrate scope, providing a variety of maleimides in generally moderate to good yields under mild reaction conditions.
{"title":"TMSOTf‐Catalyzed Annulation of Ynamides with Alkynyl Sulfoxides to Construct Substituted Maleimides","authors":"Nanfang Wang , Wozheng Fang , Yu Yan , Nan Sun , Junbiao Chang , Xiao‐Na Wang","doi":"10.1002/ajoc.202400416","DOIUrl":"10.1002/ajoc.202400416","url":null,"abstract":"<div><div>A TMSOTf‐catalyzed annulation was developed for the construction of polysubstituted maleimides from ynamides and alkynyl sulfoxides, using oxygen as a green oxidant and ynamides as both carbon and nitrogen sources. This novel protocol proceeds in the presence of TMSOTf without the need for an expensive catalytic system and tolerates a broad substrate scope, providing a variety of maleimides in generally moderate to good yields under mild reaction conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400416"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216972","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}
Deep J. Kalita , Pratiksha Bhorali , Supriya Khundrakpam , Sanjib Gogoi
A Rh(III)‐catalyzed annulation reaction of 2‐(2‐nitrovinyl)phenols and disubstituted alkynes is developed to complete the first synthesis of biologically important 4‐nitro substituted benzo[b]oxepines. The same reaction conditions are also applied for the efficient synthesis of 4‐cyano substituted benzo[b]oxepines which have high biological significance. Some of the synthesized 4‐nitrobenzo[b]oxepines are easily transformed to triazole fused dibenzo[b]oxepines.
{"title":"Rhodium(III)‐Catalyzed (5+2) Annulation Reaction for the Synthesis of Nitro and Cyano Substituted Benzo[b]Oxepines","authors":"Deep J. Kalita , Pratiksha Bhorali , Supriya Khundrakpam , Sanjib Gogoi","doi":"10.1002/ajoc.202400392","DOIUrl":"10.1002/ajoc.202400392","url":null,"abstract":"<div><div>A Rh(III)‐catalyzed annulation reaction of 2‐(2‐nitrovinyl)phenols and disubstituted alkynes is developed to complete the first synthesis of biologically important 4‐nitro substituted benzo[<em>b</em>]oxepines. The same reaction conditions are also applied for the efficient synthesis of 4‐cyano substituted benzo[<em>b</em>]oxepines which have high biological significance. Some of the synthesized 4‐nitrobenzo[<em>b</em>]oxepines are easily transformed to triazole fused dibenzo[<em>b</em>]oxepines.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":"Article e202400392"},"PeriodicalIF":2.8,"publicationDate":"2024-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142252815","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}
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