: Tulsion®-8052 MP cation resin catalyst accelerates chemical reaction by creating a suitable environment for the aldehyde and indole reactants to interact and form desired product bis(indolyl) methanes in solvent-free room temperature conditions. The uniqueness of this catalytic method is that it is eco-friendly, recyclable, selective, and operates on a variety of functional groups with good to excellent yield at room temperature conditions without the use of any hazardous solvents, high temperature, and inert atmosphere.
{"title":"Solvent-free Simplistic Synthesis of Bis(indolyl) Methanes Using Tulsion®-8052 MP Resin","authors":"Suhas Sadaphal, Sanjay Gaikwad, Shubham Dagale, Suryakant Sapkal, Pratibha Randhavane, Jaishree Gawai","doi":"10.2174/0115701786318532240722113525","DOIUrl":"https://doi.org/10.2174/0115701786318532240722113525","url":null,"abstract":": Tulsion®-8052 MP cation resin catalyst accelerates chemical reaction by creating a suitable environment for the aldehyde and indole reactants to interact and form desired product bis(indolyl) methanes in solvent-free room temperature conditions. The uniqueness of this catalytic method is that it is eco-friendly, recyclable, selective, and operates on a variety of functional groups with good to excellent yield at room temperature conditions without the use of any hazardous solvents, high temperature, and inert atmosphere.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141943358","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 the current study, we reported a cost-effective, simple strategy for the synthesis and reactivity of a novel series of chromenopyridine derivatives involving 2,4-diamino-3-carbonitrile moieties. These new compounds were synthesized in good yields from malononitrile and various chromene derivatives as a precursor, which was prepared by the reduction of iminocoumarin derivatives. The formed iminocoumarin was obtained by Knoevenagel condensation from malononitrile and different aromatic aldehydes. These novel chromenopyridine derivatives were further reacted with triethyl orthoformate under microwave irradiation to afford the final compounds, namely "chromenopyridine formimidate." The structures of all molecules were characterized by FT-IR, 1H NMR, 13C NMR, and elemental analysis.
{"title":"Microwave-assisted Synthesis and Reactivity of Some Novel Chromenopyridine Derivatives Bearing 2,4-Diamino-3-Carbonitrile Moieties","authors":"Amira Trabelsi, Emna khdhiri, Souhir Abid, Lujain M. Althobaiti, Houcine Ammar","doi":"10.2174/0115701786316461240801065332","DOIUrl":"https://doi.org/10.2174/0115701786316461240801065332","url":null,"abstract":": In the current study, we reported a cost-effective, simple strategy for the synthesis and reactivity of a novel series of chromenopyridine derivatives involving 2,4-diamino-3-carbonitrile moieties. These new compounds were synthesized in good yields from malononitrile and various chromene derivatives as a precursor, which was prepared by the reduction of iminocoumarin derivatives. The formed iminocoumarin was obtained by Knoevenagel condensation from malononitrile and different aromatic aldehydes. These novel chromenopyridine derivatives were further reacted with triethyl orthoformate under microwave irradiation to afford the final compounds, namely \"chromenopyridine formimidate.\" The structures of all molecules were characterized by FT-IR, 1H NMR, 13C NMR, and elemental analysis.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141943366","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}
Pub Date : 2024-07-29DOI: 10.2174/0115701786333234240725110033
K. venkatapathy, C. J. Magesh
In the present investigation, we report the multistep synthesis of pyranoquinolinyl acrylic acid (PQAA)/furoquinolinyl acrylic acid (FQAA) diastereomers via perkin condensation and reduction, followed by one-pot inverse electron demand Diels-Alder reaction among 2,3 dihydropyran, amine, and aromatic aldehyde mediated by indium (III) triflate in 1-butyl-3-methylimidazolium tetrafluoroborate (In(OTf)3/ [bmim]BF4) at 25.0-27.0oC. The pyranoquinolinyl acrylic acid/furoquinolinyl acrylic acid diastereomers were evaluated for their in vitro antibacterial activity. Molecular docking studies were carried out employing iGEMDOCK software to evaluate the mode of binding between UDP-N-acetylenolpyruvoyl glucosamine reductase and PQAA adducts. All the pyranoquinolinyl/ furoquinolinyl/tetrahydro-cyclopentaquinolinyl acrylic acid (PQAA/FQAA/CPQAA) diastereomers were thoroughly characterized by NMR, FT-IR, mass spectral, and CHN analysis.
{"title":"Synthesis, Spectral Characterization, Molecular Docking Studies, and Biological Evaluation of Pyranoquinolinyl Acrylic Acid (PQAA) Diastereomers as Antibacterial Agents Promoted by Indium (III) Triflate in 1-Butyl-3-Methylimidazolium Tetrafluoroborate Ionic Liquid","authors":"K. venkatapathy, C. J. Magesh","doi":"10.2174/0115701786333234240725110033","DOIUrl":"https://doi.org/10.2174/0115701786333234240725110033","url":null,"abstract":"In the present investigation, we report the multistep synthesis of pyranoquinolinyl acrylic acid (PQAA)/furoquinolinyl acrylic acid (FQAA) diastereomers via perkin condensation and reduction, followed by one-pot inverse electron demand Diels-Alder reaction among 2,3 dihydropyran, amine, and aromatic aldehyde mediated by indium (III) triflate in 1-butyl-3-methylimidazolium tetrafluoroborate (In(OTf)3/ [bmim]BF4) at 25.0-27.0oC. The pyranoquinolinyl acrylic acid/furoquinolinyl acrylic acid diastereomers were evaluated for their in vitro antibacterial activity. Molecular docking studies were carried out employing iGEMDOCK software to evaluate the mode of binding between UDP-N-acetylenolpyruvoyl glucosamine reductase and PQAA adducts. All the pyranoquinolinyl/ furoquinolinyl/tetrahydro-cyclopentaquinolinyl acrylic acid (PQAA/FQAA/CPQAA) diastereomers were thoroughly characterized by NMR, FT-IR, mass spectral, and CHN analysis.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141865564","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}
Pub Date : 2024-07-19DOI: 10.2174/0115701786315719240712070219
Mohit Gangwar, Rajnish Kumar, R. Yadav, Avijit Mazumder, Salahuddin, Neelima Kukreti, P. Tyagi, Bhupinder Kapoor
Piperazines, a class of heterocyclic compounds, have garnered significant attention in the field of organic synthesis due to their diverse pharmacological activities and widespread applications in medicinal chemistry. This review provides a comprehensive overview of the recent advancements in the synthesis of piperazines, highlighting innovative methodologies, novel reagents, and green synthesis approaches adopted by researchers. The synthesis of piperazines has witnessed remarkable progress, with a focus on developing efficient and sustainable synthetic routes. Various strategies, such as transition-metal-catalyzed reactions, microwave-assisted synthesis, photo-redox reactions, and bio-inspired methods, have emerged as powerful tools for constructing piperazine scaffolds. The review also encompasses discussions on the stereochemistry and regioselectivity issues associated with piperazine synthesis, shedding light on the intricacies of achieving specific substitution patterns. The impact of newly synthesized piperazines in drug discovery and development is also explored, emphasizing the therapeutic potential of these compounds in various disease areas. In conclusion, this review provides a comprehensive and up-to-date account of the recent advancements in piperazine synthesis, offering insights into the current state of the field and guiding future research directions. The integration of innovative methodologies and the exploration of sustainable practices underscore the ongoing efforts to streamline the synthesis of piperazines, contributing to the expansion of their applications in medicinal chemistry and related disciplines.
{"title":"Recently Adopted Synthetic Protocols for Piperazines: A Review","authors":"Mohit Gangwar, Rajnish Kumar, R. Yadav, Avijit Mazumder, Salahuddin, Neelima Kukreti, P. Tyagi, Bhupinder Kapoor","doi":"10.2174/0115701786315719240712070219","DOIUrl":"https://doi.org/10.2174/0115701786315719240712070219","url":null,"abstract":"\u0000\u0000Piperazines, a class of heterocyclic compounds, have garnered significant attention in the\u0000field of organic synthesis due to their diverse pharmacological activities and widespread applications\u0000in medicinal chemistry. This review provides a comprehensive overview of the recent advancements\u0000in the synthesis of piperazines, highlighting innovative methodologies, novel reagents, and green\u0000synthesis approaches adopted by researchers. The synthesis of piperazines has witnessed remarkable\u0000progress, with a focus on developing efficient and sustainable synthetic routes. Various strategies,\u0000such as transition-metal-catalyzed reactions, microwave-assisted synthesis, photo-redox reactions,\u0000and bio-inspired methods, have emerged as powerful tools for constructing piperazine scaffolds. The\u0000review also encompasses discussions on the stereochemistry and regioselectivity issues associated\u0000with piperazine synthesis, shedding light on the intricacies of achieving specific substitution patterns.\u0000The impact of newly synthesized piperazines in drug discovery and development is also explored,\u0000emphasizing the therapeutic potential of these compounds in various disease areas. In conclusion, this\u0000review provides a comprehensive and up-to-date account of the recent advancements in piperazine\u0000synthesis, offering insights into the current state of the field and guiding future research directions.\u0000The integration of innovative methodologies and the exploration of sustainable practices underscore\u0000the ongoing efforts to streamline the synthesis of piperazines, contributing to the expansion of their\u0000applications in medicinal chemistry and related disciplines.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141823861","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}
: This work is devoted to the synthesis of divers Michael adducts from (E)-α-atlantone as an α,β-unsaturated ketone isolated from Cedrus atlantica essential oil. The (E)-α-atlantone is subjected to ethyl cyanoacetate, phenylmagnesium bromide, and ethanol to produce the corresponding 1,4-Michael adducts in good yields. The conjugate addition of the appropriate reagents onto (E)-α-atlantone proceeds in a regiospecific manner, closely governed by the nucleophilicity of the reagents as well as their stereospecific blocking. The structure of the obtained Michael adducts is established using NMR (1H & 13C) spectroscopy and elemental analysis. Likewise, the DFT method was utilized to comprehend the molecular properties, stability, and reactivity of the investigated compounds, as well as to explain the proposed mechanism. The computed outcomes are in good agreement with the experimental data.
{"title":"Semisynthesis and DFT Study of New Michael Adducts using (E)-Α-Atlantone, Isolated from Cedrus Atlantica Essential Oil","authors":"Rida Nejjari, Maryam Bashir, Houria Raji, Bouchra Es-Sounni, Mohamed Adardour, Farhan Siddique, Mohamed Bakhouch, Abdelkrim Mouzdahir, Ahmed Benharref, Noureddine Mazoir, Samir Chtita","doi":"10.2174/0115701786321643240709114001","DOIUrl":"https://doi.org/10.2174/0115701786321643240709114001","url":null,"abstract":": This work is devoted to the synthesis of divers Michael adducts from (E)-α-atlantone as an α,β-unsaturated ketone isolated from Cedrus atlantica essential oil. The (E)-α-atlantone is subjected to ethyl cyanoacetate, phenylmagnesium bromide, and ethanol to produce the corresponding 1,4-Michael adducts in good yields. The conjugate addition of the appropriate reagents onto (E)-α-atlantone proceeds in a regiospecific manner, closely governed by the nucleophilicity of the reagents as well as their stereospecific blocking. The structure of the obtained Michael adducts is established using NMR (1H & 13C) spectroscopy and elemental analysis. Likewise, the DFT method was utilized to comprehend the molecular properties, stability, and reactivity of the investigated compounds, as well as to explain the proposed mechanism. The computed outcomes are in good agreement with the experimental data.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141737257","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}
HSP90 assists as a crucial molecular chaperone that responds to environmental stressors and helps in the survival of cells in microorganisms. This protein is integral to the stress response, aiding in the stabilization of various proteins essential for microbial survival. Consequently, the ability of a number of tissues to adjust to endogenous stress depends critically on appropriate chaperone activity. Modulators of chaperone activity, however, have emerged as a novel and developing area of drug discovery due to the association between changed chaperone function and the development of numerous illnesses. Inhibition of HSP90alpha can disrupt proper protein folding, thus impairing growth and virulence in fungi. In this work, we selected novel leads of gallic acid derivatives with the help of OSIRIS Property Explorer and DruLiTo software. Selected leads were subjected to ADME-T studies for further screening. Docking and molecular simulation studies on selected compounds were performed using Schrodinger v21 and GROMACS software to predict the bioactivity of novel leads of 3,4,5 trihydroxy benzoic acid for suppression of the HSP90alpha enzyme. Compounds 4N, 18N, 15N, and 14N showed good docking scores of -6.5, -6.4, -5.91, and -5.98, respectively, which was comparable to standard ciprofloxacin. Compound 4N and compound 14N demonstrated notable binding interactions and were selected for further investigation through molecular dynamics studies with HSP90alpha (PDB ID: 1YC1). RMSD, H BOND, and RMSF analysis confirmed the stable binding of compounds 4N and 14 N with the HSP90 enzyme. The RMSF plot showed less than 0.35 nm fluctuation for the HSP90alpha enzyme in complex with different ligands. It can be concluded that ligand binding can cause stability to the conformation of the protein. Compounds 4N and 14N are considered to be the best theoretical lead, which can further be studied experimentally as HSP90 alpha inhibitors for antimicrobial activity. Ongoing research aims to uncover more insights into the specific mechanisms of action, optimize structural features for enhanced efficacy, and explore potential synergies with existing antimicrobial agents. As a result, these derivatives hold promise as candidates for the development of novel antimicrobial agents with a broad spectrum of activity against bacteria and fungi
{"title":"Docking and Simulation Studies on Novel Analogues of 3,4,5-Trihydroxy Benzoic Acid as HSP90Alpha Inhibitors","authors":"Tanya Gupta, Ritu Kataria, Asim Kumar, Rubina Bhutani, Satish Sardana","doi":"10.2174/0115701786312992240702100154","DOIUrl":"https://doi.org/10.2174/0115701786312992240702100154","url":null,"abstract":"\u0000\u0000HSP90 assists as a crucial molecular chaperone that responds to environmental stressors\u0000and helps in the survival of cells in microorganisms. This protein is integral to the stress response,\u0000aiding in the stabilization of various proteins essential for microbial survival. Consequently, the ability\u0000of a number of tissues to adjust to endogenous stress depends critically on appropriate chaperone\u0000activity. Modulators of chaperone activity, however, have emerged as a novel and developing area of\u0000drug discovery due to the association between changed chaperone function and the development of\u0000numerous illnesses. Inhibition of HSP90alpha can disrupt proper protein folding, thus impairing\u0000growth and virulence in fungi. In this work, we selected novel leads of gallic acid derivatives with the\u0000help of OSIRIS Property Explorer and DruLiTo software. Selected leads were subjected to ADME-T\u0000studies for further screening. Docking and molecular simulation studies on selected compounds were\u0000performed using Schrodinger v21 and GROMACS software to predict the bioactivity of novel leads\u0000of 3,4,5 trihydroxy benzoic acid for suppression of the HSP90alpha enzyme. Compounds 4N, 18N,\u000015N, and 14N showed good docking scores of -6.5, -6.4, -5.91, and -5.98, respectively, which was\u0000comparable to standard ciprofloxacin. Compound 4N and compound 14N demonstrated notable binding\u0000interactions and were selected for further investigation through molecular dynamics studies with\u0000HSP90alpha (PDB ID: 1YC1). RMSD, H BOND, and RMSF analysis confirmed the stable binding of\u0000compounds 4N and 14 N with the HSP90 enzyme. The RMSF plot showed less than 0.35 nm fluctuation\u0000for the HSP90alpha enzyme in complex with different ligands. It can be concluded that ligand\u0000binding can cause stability to the conformation of the protein. Compounds 4N and 14N are considered\u0000to be the best theoretical lead, which can further be studied experimentally as HSP90 alpha inhibitors\u0000for antimicrobial activity.\u0000\u0000\u0000\u0000Ongoing research aims to uncover more insights into the specific mechanisms of action, optimize structural features for enhanced efficacy, and explore potential synergies with existing antimicrobial agents. As a result, these derivatives hold promise as candidates for the development of novel antimicrobial agents with a broad spectrum of activity against bacteria and fungi\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141653131","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}
Pub Date : 2024-07-12DOI: 10.2174/0115701786298913240709115332
Ratna Mukherjee, B. Banik
Michael addition reaction is widely accepted as the most important reaction for making carbon-carbon bonds in the synthesis of organic compounds. In this reaction, an enone is attacked by a nucleophile in a conjugated manner across a carbon-carbon double bond. The present work reported the Michael reaction of indole with α,β-unsaturated ketones via alkylation to yield 3-(3-oxoalkyl) indole or β-indolyl ketones. Naturally available orange juice has been demonstrated to be an efficient green catalyst for the Michael addition reaction of indoles with various cyclic and acyclic unsaturated ketones. The products were characterised by 1H NMR spectroscopy and compared with literature. This one-step, simple process has afforded the 3-indolyl carbonyl compounds in short reaction times and excellent yields at room temperature. The present method developed an inexpensive synthetic process to prepare substituted indoles in a simple and eco-friendly way.
{"title":"Orange Juice: A Remarkable Green Catalyst for the Michael Addition\u0000Reaction of Indoles","authors":"Ratna Mukherjee, B. Banik","doi":"10.2174/0115701786298913240709115332","DOIUrl":"https://doi.org/10.2174/0115701786298913240709115332","url":null,"abstract":"\u0000\u0000Michael addition reaction is widely accepted as the most important reaction for making\u0000carbon-carbon bonds in the synthesis of organic compounds. In this reaction, an enone is attacked by\u0000a nucleophile in a conjugated manner across a carbon-carbon double bond. The present work reported\u0000the Michael reaction of indole with α,β-unsaturated ketones via alkylation to yield 3-(3-oxoalkyl)\u0000indole or β-indolyl ketones. Naturally available orange juice has been demonstrated to be an efficient\u0000green catalyst for the Michael addition reaction of indoles with various cyclic and acyclic unsaturated\u0000ketones. The products were characterised by 1H NMR spectroscopy and compared with literature.\u0000This one-step, simple process has afforded the 3-indolyl carbonyl compounds in short reaction times\u0000and excellent yields at room temperature. The present method developed an inexpensive synthetic\u0000process to prepare substituted indoles in a simple and eco-friendly way.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141655021","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}
Pub Date : 2024-07-10DOI: 10.2174/0115701786308650240705072830
Farzaneh Ebrahimzadeh
This research work has explored the application of a magnetic catalyst composed of coreshell nanoparticles [Fe3O4@SiO2@CS@EDTA/Co(II)], known as NCM@EDTA/Co(II), in the conversion of various alcohols containing electron-donating or electron-withdrawing groups into their respective secondary or primary amine derivatives. The investigation has focused on optimizing reaction conditions by considering factors, such as the inclusion of a base, duration of reaction time, reaction temperature, catalyst quantity, and choice of transition metal, in order to determine the optimal parameters. The most favorable outcomes have been achieved by using 0.2 mmol of catalyst per 1 mmol of substrate under reflux conditions for a duration ranging from 3 to 24 hours. The reaction has demonstrated high efficiency, with the catalyst's easy separation via an external magnetic field, stability, and recyclability, highlighting its potential applications in chemistry and industrial environments.
{"title":"N-Alkylation of Amines Utilizing Magnetic Nano Chitosan Functionalized with EDTA/Co(II)","authors":"Farzaneh Ebrahimzadeh","doi":"10.2174/0115701786308650240705072830","DOIUrl":"https://doi.org/10.2174/0115701786308650240705072830","url":null,"abstract":"This research work has explored the application of a magnetic catalyst composed of coreshell nanoparticles [Fe3O4@SiO2@CS@EDTA/Co(II)], known as NCM@EDTA/Co(II), in the conversion of various alcohols containing electron-donating or electron-withdrawing groups into their respective secondary or primary amine derivatives. The investigation has focused on optimizing reaction conditions by considering factors, such as the inclusion of a base, duration of reaction time, reaction temperature, catalyst quantity, and choice of transition metal, in order to determine the optimal parameters. The most favorable outcomes have been achieved by using 0.2 mmol of catalyst per 1 mmol of substrate under reflux conditions for a duration ranging from 3 to 24 hours. The reaction has demonstrated high efficiency, with the catalyst's easy separation via an external magnetic field, stability, and recyclability, highlighting its potential applications in chemistry and industrial environments.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141587105","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 the six-membered heterocyclic compound piperazine, two nitrogen atoms are positioned within the ring at 1 and 4 positions. Numerous studies have shown that piperazine has the potential to be a useful pharmacophore in many harmful pharmacological conditions such as microbiocidal, antiinflammatory, anticancer, antioxidant, etc. In this present review, we highlighted the synthetic protocols for piperazine and its analogs, as well as the synthetic protocol for piperazine via rearrangement reaction, which have been adopted in recent years. The study also involved a listing of several patents (granted), which comprised important work on piperazine and its derivatives. Among all the methods, the most commonly adopted synthetic methods included the synthesis of piperazine analogs by dizacope, hydrolytic, mumm, multi-component, ugi-smiles, [2+3]-stevens, aza-Wittig, Curtius, Schmidt rearrangement reactions, etc. These synthetic protocols have also been compared based on different reaction conditions, feasibility, and economy to help the researchers in designing their work.
{"title":"Recent Advances in Synthetic Strategies of Piperazine & its Analogs Via\u0000Rearrangement Reactions: A Review","authors":"Upasana Sharma, Rajnish Kumar, Avijit Mazumder, Salahuddin, Neelima Kukreti, P. Tyagi, Navneet Khurana","doi":"10.2174/0115701786307643240625074530","DOIUrl":"https://doi.org/10.2174/0115701786307643240625074530","url":null,"abstract":"\u0000\u0000In the six-membered heterocyclic compound piperazine, two nitrogen atoms are positioned\u0000within the ring at 1 and 4 positions. Numerous studies have shown that piperazine has the potential to\u0000be a useful pharmacophore in many harmful pharmacological conditions such as microbiocidal, antiinflammatory, anticancer, antioxidant, etc. In this present review, we highlighted the synthetic protocols for piperazine and its analogs, as well as the synthetic protocol for piperazine via rearrangement\u0000reaction, which have been adopted in recent years. The study also involved a listing of several patents\u0000(granted), which comprised important work on piperazine and its derivatives. Among all the methods,\u0000the most commonly adopted synthetic methods included the synthesis of piperazine analogs by dizacope, hydrolytic, mumm, multi-component, ugi-smiles, [2+3]-stevens, aza-Wittig, Curtius, Schmidt\u0000rearrangement reactions, etc. These synthetic protocols have also been compared based on different\u0000reaction conditions, feasibility, and economy to help the researchers in designing their work.\u0000","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141684252","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}
: 4-Hydroxyquinoline-2(1H)-ones exhibit multiple biological activities, and studying their synthetic methods is of great significance. In the presence of tetramethylguanidine and silver nitrate, 4-hydroxyquinoline-2(1H)-ones were efficiently synthesized from 2-ethynylanilines and carbon dioxide under atmospheric pressure. The reaction conditions, such as types of silver catalysts and reaction solvents, were optimized, and the applicability of the substrate was preliminarily investigated. This method provides an alternative pathway for the synthesis of 4-hydroxyquinoline-2(1H)-ones and the conversion and utilization of carbon dioxide.
{"title":"Synthesis of 4-hydroxyquinoline-2(1H)-ones Based on Ag(I)-catalyzed Carbon Dioxide Fixation on 2-alknylanilines","authors":"Xin-Yu Lin, Guo-Jun Chen, Su-Zhe Wu, Ke-Xuan Xu, Xiao-Tian Zhang, Qi Feng","doi":"10.2174/0115701786302455240603070018","DOIUrl":"https://doi.org/10.2174/0115701786302455240603070018","url":null,"abstract":": 4-Hydroxyquinoline-2(1H)-ones exhibit multiple biological activities, and studying their synthetic methods is of great significance. In the presence of tetramethylguanidine and silver nitrate, 4-hydroxyquinoline-2(1H)-ones were efficiently synthesized from 2-ethynylanilines and carbon dioxide under atmospheric pressure. The reaction conditions, such as types of silver catalysts and reaction solvents, were optimized, and the applicability of the substrate was preliminarily investigated. This method provides an alternative pathway for the synthesis of 4-hydroxyquinoline-2(1H)-ones and the conversion and utilization of carbon dioxide.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141530305","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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