Pu-Fan Qian, Jun-Yi Li, Yi-Bo Zhou, Tao Zhou, Bing‐Feng Shi
Transition metal-catalyzed enantioselective C–H activation has provided a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphic review, we summarized the progress of half-sandwich d6 metal (CoIII, RhIII, IrIII, RuII) catalyzed enantioselective C–H functionalization reactions. The review was categorized according to the types of metal catalysts and chiral ligands. Representative enantio-determining models and catalytic cycles were presented. We hope this graphic review would stimulate further efforts on the development of novel chiral ligands and strategies in this emerging research topic.
{"title":"Half-Sandwich d 6 -Metal (Co III , Rh III , Ir III , Ru II )-Catalyzed Enantioselective C–H Activation","authors":"Pu-Fan Qian, Jun-Yi Li, Yi-Bo Zhou, Tao Zhou, Bing‐Feng Shi","doi":"10.1055/a-2167-8298","DOIUrl":"https://doi.org/10.1055/a-2167-8298","url":null,"abstract":"Transition metal-catalyzed enantioselective C–H activation has provided a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphic review, we summarized the progress of half-sandwich d6 metal (CoIII, RhIII, IrIII, RuII) catalyzed enantioselective C–H functionalization reactions. The review was categorized according to the types of metal catalysts and chiral ligands. Representative enantio-determining models and catalytic cycles were presented. We hope this graphic review would stimulate further efforts on the development of novel chiral ligands and strategies in this emerging research topic.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"466 - 485"},"PeriodicalIF":2.5,"publicationDate":"2023-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45047351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this spotlight, we have compiled the significant contributions of 2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) in both organic synthesis and catalysis starting from 2015 to date.
{"title":"Recent Applications of TEMPO in Organic Synthesis and Catalysis","authors":"Dr. Ravi Varala, Vittal Seema","doi":"10.1055/a-2155-2950","DOIUrl":"https://doi.org/10.1055/a-2155-2950","url":null,"abstract":"In this spotlight, we have compiled the significant contributions of 2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO) in both organic synthesis and catalysis starting from 2015 to date.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"408 - 413"},"PeriodicalIF":2.5,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44580412","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A practical syntheses of sorafenib and regorafenib have been achieved in an efficient manner which is free from the problems associated with the methods described in literature. The process involved preparation of 4-(4-aminophenoxy)-N-methylpicolinamide (Sorafenib intermediate) and 4-(4-amino-3-fluorophenoxy)-N-methylpicolinamide (Regorafenib intermediate) using only one base and avoided use of inert atmosphere. The reaction of intermediates with phenyl (4-chloro-3-(trifluoromethyl)phenyl)carbamate - prepared using water-assisted synthesis of carbamates – installed the main urea functionality in these molecules.
{"title":"A Practical and Efficient Method for the Synthesis of Sorafenib and Regorafenib","authors":"Ramteke Prachi, M. Gill","doi":"10.1055/a-2157-5855","DOIUrl":"https://doi.org/10.1055/a-2157-5855","url":null,"abstract":"A practical syntheses of sorafenib and regorafenib have been achieved in an efficient manner which is free from the problems associated with the methods described in literature. The process involved preparation of 4-(4-aminophenoxy)-N-methylpicolinamide (Sorafenib intermediate) and 4-(4-amino-3-fluorophenoxy)-N-methylpicolinamide (Regorafenib intermediate) using only one base and avoided use of inert atmosphere. The reaction of intermediates with phenyl (4-chloro-3-(trifluoromethyl)phenyl)carbamate - prepared using water-assisted synthesis of carbamates – installed the main urea functionality in these molecules.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"422 - 429"},"PeriodicalIF":2.5,"publicationDate":"2023-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45121697","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Michiyasu Nakao, Akihito Nakamura, T. Takesue, Syuji Kitaike, Hiro-o Ito, S. Sano
A three-component coupling reaction of ortho-phthalaldehyde, 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide, and various primary amines readily afforded novel phosphorus-substituted stable isoindoles in good to excellent yields. The importance of the reversible ring-opening of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide by methanolysis in the three-component coupling reaction became apparent.
{"title":"Synthesis of Novel Phosphorus-Substituted Stable Isoindoles by a Three-Component Coupling Reaction of ortho -Phthalaldehyde, 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide, and Primary Amines","authors":"Michiyasu Nakao, Akihito Nakamura, T. Takesue, Syuji Kitaike, Hiro-o Ito, S. Sano","doi":"10.1055/a-2148-9433","DOIUrl":"https://doi.org/10.1055/a-2148-9433","url":null,"abstract":"A three-component coupling reaction of ortho-phthalaldehyde, 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide, and various primary amines readily afforded novel phosphorus-substituted stable isoindoles in good to excellent yields. The importance of the reversible ring-opening of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide by methanolysis in the three-component coupling reaction became apparent.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"394 - 400"},"PeriodicalIF":2.5,"publicationDate":"2023-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46199662","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nathan R. Long, A. Le Gresley, Arran Solomonsz, Antony Wozniak, Steve Brough, S. Wren
Herein, we present a synthetic compound library comprising of 28 anilino and benzylamino monosquarate-amide derivatives. Members of this library were designed as bioisosteric replacements for groups such as the ubiquitous carboxylic acid moiety. Further to their synthesis, we have shown the potential of these chemical building blocks for the generation of additional novel compounds. This work forms part of our efforts aimed at the assembly of 96-well plates loaded with bioisosteric analogues that may be used to enrich drug discovery programs. The research presented in this work focuses on the chemistry of 3,4-dihydroxycyclobut-3-ene-1,2-dione, a known carboxylic acid bioisostere.
{"title":"Synthesis of Squaric Acid Monoamides as Building Blocks for Drug Discovery","authors":"Nathan R. Long, A. Le Gresley, Arran Solomonsz, Antony Wozniak, Steve Brough, S. Wren","doi":"10.1055/a-2148-9518","DOIUrl":"https://doi.org/10.1055/a-2148-9518","url":null,"abstract":"Herein, we present a synthetic compound library comprising of 28 anilino and benzylamino monosquarate-amide derivatives. Members of this library were designed as bioisosteric replacements for groups such as the ubiquitous carboxylic acid moiety. Further to their synthesis, we have shown the potential of these chemical building blocks for the generation of additional novel compounds. This work forms part of our efforts aimed at the assembly of 96-well plates loaded with bioisosteric analogues that may be used to enrich drug discovery programs. The research presented in this work focuses on the chemistry of 3,4-dihydroxycyclobut-3-ene-1,2-dione, a known carboxylic acid bioisostere.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"401 - 407"},"PeriodicalIF":2.5,"publicationDate":"2023-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47159778","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Benzimidazoles and benzothiazoles are a class of pharmacologically potential compounds, which exhibited anti-microbial, anticancer, and anti-inflammatory activities. These can be obtained by simple condensation of o-phenylenediamine or o-aminothiophenol with aromatic aldehydes. The synthetic protocol can be accomplished/improved by varying reaction parameters such as temperature, solvents, and catalysts. To develop such condensation reactions in a sustainable way, non-toxic solvents and eco- friendly catalysts are presently used. In this study, we proposed a novel and interesting strategy for obtaining diversely substituted 2-phenyl benzimidazole and 2-phenyl benzothiazole derivatives via a one-pot protocol, employing pyrrolidinium ionic liquid as a green and environmentally benign catalyst under solvent-free conditions at room temperature in an open atmosphere. The resulting products were obtained in good to excellent yields within a short reaction time (3-20 min). A plausible mechanism was also discussed.
{"title":"Pyrrolidinium Acetate (PyrrIL) as a Green and Recyclable Catalyst: Synthesis of 2-Phenyl Benzimidazoles and 2-Phenyl Benzothiazoles under Solvent-Free Conditions at Room Temperature","authors":"Ramesh Katla, Rakhi Katla","doi":"10.1055/a-2149-4113","DOIUrl":"https://doi.org/10.1055/a-2149-4113","url":null,"abstract":"Benzimidazoles and benzothiazoles are a class of pharmacologically potential compounds, which exhibited anti-microbial, anticancer, and anti-inflammatory activities. These can be obtained by simple condensation of o-phenylenediamine or o-aminothiophenol with aromatic aldehydes. The synthetic protocol can be accomplished/improved by varying reaction parameters such as temperature, solvents, and catalysts. To develop such condensation reactions in a sustainable way, non-toxic solvents and eco- friendly catalysts are presently used. In this study, we proposed a novel and interesting strategy for obtaining diversely substituted 2-phenyl benzimidazole and 2-phenyl benzothiazole derivatives via a one-pot protocol, employing pyrrolidinium ionic liquid as a green and environmentally benign catalyst under solvent-free conditions at room temperature in an open atmosphere. The resulting products were obtained in good to excellent yields within a short reaction time (3-20 min). A plausible mechanism was also discussed.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"414 - 421"},"PeriodicalIF":2.5,"publicationDate":"2023-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43371163","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Rawat, Pradeep Kumar, Preetam Kumar, Kamal Singh
The acid catalyzed reaction is one of the most important reactions in organic chemistry. Most acid catalyzed reactions have been studied in the presence of strong acids such as H2SO4, HNO3, HCl, BF3.O(Et)2, TFA, and methanesulfonic acid etc. in various organic solvents. The use of excessive and even stoichiometric amounts of acids with organic solvents raises environmental concerns. To avoid the use of corrosive acids and to reduce the environmental impact, the development of a new method for organic synthesis catalyzed by boric acid would be highly desirable. The benefits and uses of boric acid-catalyzed reactions were covered in this communication.
{"title":"Boric acid: A Mild and Efficient Green Catalyst for Organic Transformations","authors":"A. Rawat, Pradeep Kumar, Preetam Kumar, Kamal Singh","doi":"10.1055/a-2110-2785","DOIUrl":"https://doi.org/10.1055/a-2110-2785","url":null,"abstract":"The acid catalyzed reaction is one of the most important reactions in organic chemistry. Most acid catalyzed reactions have been studied in the presence of strong acids such as H2SO4, HNO3, HCl, BF3.O(Et)2, TFA, and methanesulfonic acid etc. in various organic solvents. The use of excessive and even stoichiometric amounts of acids with organic solvents raises environmental concerns. To avoid the use of corrosive acids and to reduce the environmental impact, the development of a new method for organic synthesis catalyzed by boric acid would be highly desirable. The benefits and uses of boric acid-catalyzed reactions were covered in this communication.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2023-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48753999","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kavita Singh, Rajdeep Tyagi, V. Mishra, Ghanshyam Tiwari, R. Sagar
Carbohydrates, traditionally known for their energy-providing role, have gained significant attention in drug discovery due to their diverse bioactivities and stereodiversity. However, pure carbohydrate molecules often exhibit limited bioactivity and suboptimal chemical and physical characteristics. To address these challenges, functional groups with bioactive scaffolds have been incorporated into carbohydrate to enhance their bioactivity and improve their overall properties. Among the various synthetic methods available, click chemistry has emerged as a powerful tool for the synthesis of carbohydrate-containing bioactive scaffolds, known as glycohybrids. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification and compatibility with multiple functional groups. In the present review, we have emphasized the recent advances and most pertinent research on the development of 1,2,3-triazole-containing glycohybrids using click reaction, their biological evaluations and the structure-activity relationship during 2017-2023. These newly synthesised glycohybrids could potentially be developed as new chemical entities (NCE) in pharmaceutical chemistry and may encourage the use of carbohydrates in drug discovery processes. 1 Introduction 2 CuAAC click chemistry mediated synthesis of triazole based glycohybrids and their biological activities 3 Conclusions and perspective
{"title":"Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry","authors":"Kavita Singh, Rajdeep Tyagi, V. Mishra, Ghanshyam Tiwari, R. Sagar","doi":"10.1055/a-2130-7319","DOIUrl":"https://doi.org/10.1055/a-2130-7319","url":null,"abstract":"Carbohydrates, traditionally known for their energy-providing role, have gained significant attention in drug discovery due to their diverse bioactivities and stereodiversity. However, pure carbohydrate molecules often exhibit limited bioactivity and suboptimal chemical and physical characteristics. To address these challenges, functional groups with bioactive scaffolds have been incorporated into carbohydrate to enhance their bioactivity and improve their overall properties. Among the various synthetic methods available, click chemistry has emerged as a powerful tool for the synthesis of carbohydrate-containing bioactive scaffolds, known as glycohybrids. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification and compatibility with multiple functional groups. In the present review, we have emphasized the recent advances and most pertinent research on the development of 1,2,3-triazole-containing glycohybrids using click reaction, their biological evaluations and the structure-activity relationship during 2017-2023. These newly synthesised glycohybrids could potentially be developed as new chemical entities (NCE) in pharmaceutical chemistry and may encourage the use of carbohydrates in drug discovery processes.\u00001 Introduction \u00002 CuAAC click chemistry mediated synthesis of triazole based glycohybrids and their biological activities \u00003 Conclusions and perspective \u0000","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"322 - 352"},"PeriodicalIF":2.5,"publicationDate":"2023-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49667314","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sushma B Singh, Sidhant Yadav, Minakshi Minakshi, R. Pundeer
Abstract Organic syntheses by adopting green protocols such as sonochemical procedures, microwave technologies, solvent-free conditions, green solvent, heterogeneous catalysis particularly nanocatalysts, ionic liquids have replaced the traditional procedures due to concerns pertaining especially to environment. The heterocycle, pyrazole, due to its multifaceted applications has been the cyanosure of the chemists and therefore various synthetic approaches have been developed to synthesize the pyrazole containing molecules. In the present compilation, we have summarized the recent water-based research work on the synthesis of pyrazoles. Key words: Green chemistry, environment friendly, water based synthesis, pyrazoles
{"title":"Green Synthesis of Pyrazoles: Recent Developments in Aqueous Methods","authors":"Sushma B Singh, Sidhant Yadav, Minakshi Minakshi, R. Pundeer","doi":"10.1055/a-2123-8102","DOIUrl":"https://doi.org/10.1055/a-2123-8102","url":null,"abstract":"Abstract Organic syntheses by adopting green protocols such as sonochemical procedures, microwave technologies, solvent-free conditions, green solvent, heterogeneous catalysis particularly nanocatalysts, ionic liquids have replaced the traditional procedures due to concerns pertaining especially to environment. The heterocycle, pyrazole, due to its multifaceted applications has been the cyanosure of the chemists and therefore various synthetic approaches have been developed to synthesize the pyrazole containing molecules. In the present compilation, we have summarized the recent water-based research work on the synthesis of pyrazoles. \u0000Key words: Green chemistry, environment friendly, water based synthesis, pyrazoles","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"297 - 312"},"PeriodicalIF":2.5,"publicationDate":"2023-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49229815","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dominance of fossil fuel in energy sector is associated with greenhouse gas emission and release of atmospheric pollutants. Biomass based energy generation is considered as potential alternative for replacement of fossil fuels as it is being used as a sustainable source of heat and power since long time. Biomass as a feedstock can be used for synthesis of different energy products. Catalyst plays significant role in various conversion routs and affect the yield of major products. Researchers have mainly focused on starchy feedstock, lignocellulosic biomass and triglyceride containing biomass for bioenergy production. The catalytic reactions for the biomass feedstock mainly involves deoxygenation, hydrolysis, hydrogenation, dehydrogenation and oxidation etc. This review mainly focuses on the overview of various catalytic reactions for conversion of different class of biomass feedstock for biofuel production. The primary aim of this review is to provide catalytic strategies for conversion of lignocellulosic biomass to value-added products
{"title":"Heterogeneous Catalysis for Sustainable Energy","authors":"Jaya Tuteja","doi":"10.1055/a-2129-9076","DOIUrl":"https://doi.org/10.1055/a-2129-9076","url":null,"abstract":"Dominance of fossil fuel in energy sector is associated with greenhouse gas emission and release of atmospheric pollutants. Biomass based energy generation is considered as potential alternative for replacement of fossil fuels as it is being used as a sustainable source of heat and power since long time. Biomass as a feedstock can be used for synthesis of different energy products. Catalyst plays significant role in various conversion routs and affect the yield of major products. Researchers have mainly focused on starchy feedstock, lignocellulosic biomass and triglyceride containing biomass for bioenergy production. The catalytic reactions for the biomass feedstock mainly involves deoxygenation, hydrolysis, hydrogenation, dehydrogenation and oxidation etc. This review mainly focuses on the overview of various catalytic reactions for conversion of different class of biomass feedstock for biofuel production. The primary aim of this review is to provide catalytic strategies for conversion of lignocellulosic biomass to value-added products","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"07 1","pages":"353 - 361"},"PeriodicalIF":2.5,"publicationDate":"2023-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49116054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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