Pub Date : 2021-08-25DOI: 10.2174/2213337208666210825112301
Aditi Sharma, Gurpreet Kaur, Diksha Singh, V. Gupta, B. Banerjee
Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives under greener conditions. Quinoxaline and related skeletons are very common in naturally occurring bioactive compounds. Design a facile, green and organo-catalyzed method for the synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives. Both the scaffolds were synthesized via the condensation of ninhydrin and o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of mandelic acid as an efficient, commercially available, low cost, organo-catalyst in aqueous ethanol at room temperature. Mild reaction conditions, use of metal-free organocatalyst, non-toxic solvent, ambient temperature, and no column chromatographic separation are some of the notable advantages of our developed protocol. In conclusion, we have developed a simple, mild, facile and efficient method for the synthesis of structurally diverse 11H-indeno[1,2-b]quinoxalin-11-one derivatives via the condensation reactions of ninhydrin and various substituted benzene-1,2-diamines using a catalytic amount of mandelic acid as a commercially available metal-free organo-catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives was also accomplished with excellent yields by using pyridine-2,3-diamines instead of o-phenylenediamine.
{"title":"A General Method for the Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones and 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one Derivatives using Mandelic Acid as an Efficient Organo-catalyst at Room Temperature","authors":"Aditi Sharma, Gurpreet Kaur, Diksha Singh, V. Gupta, B. Banerjee","doi":"10.2174/2213337208666210825112301","DOIUrl":"https://doi.org/10.2174/2213337208666210825112301","url":null,"abstract":"\u0000\u0000Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives under greener conditions.\u0000\u0000\u0000\u0000\u0000Quinoxaline and related skeletons are very common in naturally occurring bioactive compounds.\u0000\u0000\u0000\u0000\u0000 Design a facile, green and organo-catalyzed method for the synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives.\u0000\u0000\u0000\u0000\u0000 Both the scaffolds were synthesized via the condensation of ninhydrin and o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of mandelic acid as an efficient, commercially available, low cost, organo-catalyst in aqueous ethanol at room temperature.\u0000\u0000\u0000\u0000\u0000 Mild reaction conditions, use of metal-free organocatalyst, non-toxic solvent, ambient temperature, and no column chromatographic separation are some of the notable advantages of our developed protocol.\u0000\u0000\u0000\u0000\u0000In conclusion, we have developed a simple, mild, facile and efficient method for the synthesis of structurally diverse 11H-indeno[1,2-b]quinoxalin-11-one derivatives via the condensation reactions of ninhydrin and various substituted benzene-1,2-diamines using a catalytic amount of mandelic acid as a commercially available metal-free organo-catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives was also accomplished with excellent yields by using pyridine-2,3-diamines instead of o-phenylenediamine.\u0000\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47890882","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}
Pub Date : 2021-08-16DOI: 10.2174/2213337208666210816110719
Qian Yang, Na Ma, Yangqing He, Xiaojiao Yu, B. Yao
The synthesis of 5-arylation uracil nucleosides is an imperative challenge. Especially for the method of suzuki reaction using N-unprotected uracil as materials, which holds potential to enhance the yield. In order to find a more efficient catalyst to increase the yield of aryluracils and aryluridines. We first constructed the phosphanamine-grafted cellulose (PAGC) from cellulose material. And then prepared the nanocatalyst PAGC/Pd(0) through heating and reducing the mixture of PAGC and Pa(OAc)2. When using this nanocatalyst to catalyze the Suzuki reaction of 5-iodouracil or 5-iodouridine and aryl heterocyclic boronic acids. The arylation yields have been a significantly improvement. This means that the resultant nanocatalyst exhibits a remarkable catalytic efficacy for Suzuki arylation of 5-iodouracil and 5-iodouridine.
{"title":"Immobilized Palladium nanoparticles on phosphanamine-grafted cellulose for arylation of uracil","authors":"Qian Yang, Na Ma, Yangqing He, Xiaojiao Yu, B. Yao","doi":"10.2174/2213337208666210816110719","DOIUrl":"https://doi.org/10.2174/2213337208666210816110719","url":null,"abstract":"\u0000\u0000The synthesis of 5-arylation uracil nucleosides is an imperative challenge. Especially for the method of suzuki reaction using N-unprotected uracil as materials, which holds potential to enhance the yield. \u0000\u0000\u0000\u0000In order to find a more efficient catalyst to increase the yield of aryluracils and aryluridines. \u0000\u0000\u0000\u0000\u0000We first constructed the phosphanamine-grafted cellulose (PAGC) from cellulose material. And then prepared the nanocatalyst PAGC/Pd(0) through heating and reducing the mixture of PAGC and Pa(OAc)2. \u0000\u0000\u0000\u0000When using this nanocatalyst to catalyze the Suzuki reaction of 5-iodouracil or 5-iodouridine and aryl heterocyclic boronic acids. The arylation yields have been a significantly improvement. \u0000\u0000\u0000\u0000This means that the resultant nanocatalyst exhibits a remarkable catalytic efficacy for Suzuki arylation of 5-iodouracil and 5-iodouridine.\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46613642","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}
Pub Date : 2021-07-26DOI: 10.2174/2213337208666210726141934
M. Shirzad, Mitra Nasiri, Nader Daneshvar, F. Shirini, H. Tajik
In this work, we have prepared two bis-dicationic ionic liquids with the same cationic core (Bis-imidazole) and different counter-anions using sulfuric acid and perchloric acids. After that, the efficiency and ability of these compounds as catalysts were investigated and compared in the promotion of Knoevenagel condensation and synthesis of benzo[b]pyran derivatives to see the effect of the anionic counter-part in the reaction. In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (2.0 mmol) and the desired amount of the mentioned acidic ionic liquids was heated at 90°C in the absence of solvent (Reaction A) or In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (1.0 mmol), malononitrile, (1.1 mmol) and optimized amounts of the ionic liquid in water (3.0 mL) was heated at 80°C (Reaction B) for the appropriated time. After the completion of the reactions which were monitored by TLC (n-hexane: EtOAc; 3:1), 10 mL of water was added and the mixture was stirred for 2 minutes. Then, the products were separated by filtration and were washed several times with water. After drying, the pure products were obtained while there was no need to further. Comparison of the obtained results from both of the ionic liquids revealed that [H2-Bisim][HSO4]2 because of its more acidic structure had a more catalytic activity for the preparation of 1,8-dioxo-octahydro-xanthene derivatives but [H2-Bisim][ClO4]2 was relatively more efficient for the synthesis of tetrahydrobenzo[b]pyran derivatives since the stronger acidic nature of [H2-Bisim][HSO4]2 may prevent the simple activation of malononitrile in the reaction media. In this study, we have introduced efficient methods for the synthesis of 1,8-dioxo-octahydro-xanthene and tetrahydrobenzo[b]pyran derivatives in the presence of catalytic amounts of [H2-Bisim][ClO4]2 and [H2-Bisim][HSO4]2 These methods have several advantages such as ease of preparation and handling of the catalysts, high reaction rates, excellent yields, eco-friendly procedures and simple work-up.
{"title":"Synthesis of 1,8-dioxo-octahydro-xanthene and tetrahydrobenzo[b]pyran derivatives promoted by two bis-imidazolium-based ionic liquids","authors":"M. Shirzad, Mitra Nasiri, Nader Daneshvar, F. Shirini, H. Tajik","doi":"10.2174/2213337208666210726141934","DOIUrl":"https://doi.org/10.2174/2213337208666210726141934","url":null,"abstract":"\u0000\u0000In this work, we have prepared two bis-dicationic ionic liquids with the same cationic core (Bis-imidazole) and different counter-anions using sulfuric acid and perchloric acids. After that, the efficiency and ability of these compounds as catalysts were investigated and compared in the promotion of Knoevenagel condensation and synthesis of benzo[b]pyran derivatives to see the effect of the anionic counter-part in the reaction.\u0000\u0000\u0000\u0000In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (2.0 mmol) and the desired amount of the mentioned acidic ionic liquids was heated at 90°C in the absence of solvent (Reaction A) or In a 25 mL round-bottomed flask, a mixture of aldehyde (1.0 mmol), 1,3-cyclodicarbonyl (1.0 mmol), malononitrile, (1.1 mmol) and optimized amounts of the ionic liquid in water (3.0 mL) was heated at 80°C (Reaction B) for the appropriated time. After the completion of the reactions which were monitored by TLC (n-hexane: EtOAc; 3:1), 10 mL of water was added and the mixture was stirred for 2 minutes. Then, the products were separated by filtration and were washed several times with water. After drying, the pure products were obtained while there was no need to further.\u0000\u0000\u0000\u0000Comparison of the obtained results from both of the ionic liquids revealed that [H2-Bisim][HSO4]2 because of its more acidic structure had a more catalytic activity for the preparation of 1,8-dioxo-octahydro-xanthene derivatives but [H2-Bisim][ClO4]2 was relatively more efficient for the synthesis of tetrahydrobenzo[b]pyran derivatives since the stronger acidic nature of [H2-Bisim][HSO4]2 may prevent the simple activation of malononitrile in the reaction media.\u0000\u0000\u0000\u0000In this study, we have introduced efficient methods for the synthesis of 1,8-dioxo-octahydro-xanthene and tetrahydrobenzo[b]pyran derivatives in the presence of catalytic amounts of [H2-Bisim][ClO4]2 and [H2-Bisim][HSO4]2 These methods have several advantages such as ease of preparation and handling of the catalysts, high reaction rates, excellent yields, eco-friendly procedures and simple work-up.\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47619105","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}
Pub Date : 2021-07-19DOI: 10.2174/2213337208666210719102301
Aparna Das, B. Banik
Ascorbic acid, also known as Vitamin C, is the essential vitamin observed in diverse food. Ascorbic acid has various applications in several fields. Studies have depicted that in organic synthesis, it can be used as a mediator or substrate. The derivatives of ascorbic acid have been found to possess numerous biological activities. In this review, we report the crucial derivatives of ascorbic acid, which have significant biological activities. Various studies are considered in this review to prove its wide range of availability.
{"title":"Versatile Synthesis of Organic Compounds Derived from Ascorbic Acid.","authors":"Aparna Das, B. Banik","doi":"10.2174/2213337208666210719102301","DOIUrl":"https://doi.org/10.2174/2213337208666210719102301","url":null,"abstract":"\u0000\u0000Ascorbic acid, also known as Vitamin C, is the essential vitamin observed in diverse food. Ascorbic acid has various applications in several fields. Studies have depicted that in organic synthesis, it can be used as a mediator or substrate. The derivatives of ascorbic acid have been found to possess numerous biological activities. In this review, we report the crucial derivatives of ascorbic acid, which have significant biological activities. Various studies are considered in this review to prove its wide range of availability. \u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46009467","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}
Pub Date : 2021-07-19DOI: 10.2174/2213337208666210719101409
Rammyani Pal, C. Mukhopadhyay
Organocatalysis has been established to be a wide-applicable approach from its inception and rediscovery in 2000. Proline was used as a catalyst in aldol condensation and soon after the successful emergence of iminium catalyzed reactions in organic synthesis. The development of new potential catalytic systems is always an essential and uphill task for scientists and researchers. The fundamental organic synthesis majorly deals with metal-based catalysts, whereas there is a constant surge of developing metal-free reaction conditions to make the reactions environmental friendly. For the synthesis of complex organic molecules, reduction and oxidation reactions are always needed, and there are plenty of catalysts available for these reactions. Organocatalysts are also developed and applied for these two elementary reactions. This review focuses on some of the latest developments and applications of organocatalystsin oxidation and reduction reactions in fundamental organic synthesis.
{"title":"Organocatalysis: An overview on its application in oxidation and reduction reactions","authors":"Rammyani Pal, C. Mukhopadhyay","doi":"10.2174/2213337208666210719101409","DOIUrl":"https://doi.org/10.2174/2213337208666210719101409","url":null,"abstract":"\u0000\u0000Organocatalysis has been established to be a wide-applicable approach from its inception and rediscovery in 2000. Proline was used as a catalyst in aldol condensation and soon after the successful emergence of iminium catalyzed reactions in organic synthesis. The development of new potential catalytic systems is always an essential and uphill task for scientists and researchers. The fundamental organic synthesis majorly deals with metal-based catalysts, whereas there is a constant surge of developing metal-free reaction conditions to make the reactions environmental friendly. For the synthesis of complex organic molecules, reduction and oxidation reactions are always needed, and there are plenty of catalysts available for these reactions. Organocatalysts are also developed and applied for these two elementary reactions. This review focuses on some of the latest developments and applications of organocatalystsin oxidation and reduction reactions in fundamental organic synthesis.\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43826335","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}
Pub Date : 2021-07-19DOI: 10.2174/2213337208666210719093403
V. Srivastava
Presently worldwide manufacturing of formic acid follows the permutation of methanol and carbon monoxide in the presence of a strong base. But due to the use of toxic CO molecules and easy availability of CO2 molecules in the atmosphere, most of the research has been shifted from the conventional method of formic acid synthesis to direct hydrogenation of CO2 gas using different homogenous and heterogeneous catalysts. The study aims to develop a reaction protocol to achieve easy CO2 hydrogenation to formic acid using an Ionic liquid reaction medium. We used the sol-gel method followed by calcination (over 250oC for 5 hours) to synthesize two types of ruthenium metal-doped TiO2 nanoparticles (with and without ionic liquids) Ru@TiO2@IL and Ru@TiO2. We report the application NR2 (R= CH3) containing imidazolium-based ionic liquids to achieve a good reaction rate and get agglomeration free ruthenium metal-doped TiO2 nanoparticles along with easy product isolation due to the presence of NR2 (R= CH3) functionality in ionic liquid structure. We synthesized various NR2 (R= CH3) functionalized ionic liquids such as 1-Butyl-3-methylimidazolium Chloride, 1,3-di(N,N-dimethylaminoethyl)-2-methylimidazolium trifluoromethane sulfonate ([DAMI][TfO]), 1,3-di(N,N-dimethylaminoethyl)-2-methylimidazolium bis (trifluoromethylsulfonyl) imide ([DAMI][NTf2]) and 1-butyl-3-methylimidazolium chloride ionic liquids were synthesized as per the reported procedure. We quickly developed two typed of Ru metal-doped TiO2 nanoparticles using the sol-gel method. After calcination, both Ru@TiO2@IL (3.2 wt% Ru), and Ru@TiO2 (1.7 wt% Ru) materials were characterized by XRD, FTIR, TEM, ICP-AES, EDS, and XANES analysis. After understanding the correct structural arrangement of Ru metal over TiO2 support, we utilized both Ru@TiO2@IL (3.2 wt% Ru) and Ru@TiO2 (1.7 wt% Ru) the materials as a catalyst for direct hydrogenation of CO2 in the presence of water. We functionalized [DAMI] [TfO] ionic liquid. After understanding the correct morphology and physiochemical analysis of Ru@TiO2@IL (3.2 wt% Ru), and Ru@TiO2 (1.7 wt% Ru) catalysts, we examined their application in CO2 reduction and formic acid synthesis. Here we demonstrated the preparation and characterization of TiO2 supported Ru nanoparticles with and without ionic liquid. We also noticed the significant effect of functionalized [DAMI] [TfO] ionic liquid and water to improve the formic acid yield during the optimization. Last, we also checked the stability of the catalyst by recycling the same till the 7th run.
{"title":"Direct Synthesis of Formic acid from Carbon Dioxide by Hydrogenation over Ruthenium Metal Doped Titanium Dioxide Nanoparticles in Functionalized Ionic Liquid","authors":"V. Srivastava","doi":"10.2174/2213337208666210719093403","DOIUrl":"https://doi.org/10.2174/2213337208666210719093403","url":null,"abstract":"\u0000\u0000Presently worldwide manufacturing of formic acid follows the permutation of methanol and carbon monoxide in the presence of a strong base. But due to the use of toxic CO molecules and easy availability of CO2 molecules in the atmosphere, most of the research has been shifted from the conventional method of formic acid synthesis to direct hydrogenation of CO2 gas using different homogenous and heterogeneous catalysts.\u0000\u0000\u0000\u0000The study aims to develop a reaction protocol to achieve easy CO2 hydrogenation to formic acid using an Ionic liquid reaction medium.\u0000\u0000\u0000\u0000We used the sol-gel method followed by calcination (over 250oC for 5 hours) to synthesize two types of ruthenium metal-doped TiO2 nanoparticles (with and without ionic liquids) Ru@TiO2@IL and Ru@TiO2. We report the application NR2 (R= CH3) containing imidazolium-based ionic liquids to achieve a good reaction rate and get agglomeration free ruthenium metal-doped TiO2 nanoparticles along with easy product isolation due to the presence of NR2 (R= CH3) functionality in ionic liquid structure. We synthesized various NR2 (R= CH3) functionalized ionic liquids such as 1-Butyl-3-methylimidazolium Chloride, 1,3-di(N,N-dimethylaminoethyl)-2-methylimidazolium trifluoromethane sulfonate ([DAMI][TfO]), 1,3-di(N,N-dimethylaminoethyl)-2-methylimidazolium bis (trifluoromethylsulfonyl) imide ([DAMI][NTf2]) and 1-butyl-3-methylimidazolium chloride ionic liquids were synthesized as per the reported procedure.\u0000\u0000\u0000\u0000We quickly developed two typed of Ru metal-doped TiO2 nanoparticles using the sol-gel method. After calcination, both Ru@TiO2@IL (3.2 wt% Ru), and Ru@TiO2 (1.7 wt% Ru) materials were characterized by XRD, FTIR, TEM, ICP-AES, EDS, and XANES analysis. After understanding the correct structural arrangement of Ru metal over TiO2 support, we utilized both Ru@TiO2@IL (3.2 wt% Ru) and Ru@TiO2 (1.7 wt% Ru) the materials as a catalyst for direct hydrogenation of CO2 in the presence of water. We functionalized [DAMI] [TfO] ionic liquid.\u0000\u0000\u0000\u0000After understanding the correct morphology and physiochemical analysis of Ru@TiO2@IL (3.2 wt% Ru), and Ru@TiO2 (1.7 wt% Ru) catalysts, we examined their application in CO2 reduction and formic acid synthesis. Here we demonstrated the preparation and characterization of TiO2 supported Ru nanoparticles with and without ionic liquid. We also noticed the significant effect of functionalized [DAMI] [TfO] ionic liquid and water to improve the formic acid yield during the optimization. Last, we also checked the stability of the catalyst by recycling the same till the 7th run.\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42876128","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}
Pub Date : 2021-07-19DOI: 10.2174/2213337208666210719100147
V. Srivastava
Baylis-Hillman reaction suffers from the requirement of cheap starting materials, easy reaction protocol, possibility to create the chiral center in the reaction product has increased the synthetic efficacy of this reaction, and high catalyst loading, low reaction rate, and poor yield. The extensive use of various functional or non-functional ionic liquids (ILs) with organocatalyst increases the reaction rate of various organic transformations as a reaction medium and as a support to anchor the catalysts. In this manuscript, we have demonstrated the synthesis of quinuclidine-supported trimethylamine-based functionalized ionic liquid as a catalyst for the Baylis-Hillman reaction. We obtained the Baylis-Hillman adducts in good, isolated yield, low catalyst loading, short reaction time, broad substrate scope, accessible product, and catalyst recycling. N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide was also successfully synthesized using CATALYST-3 promoted Baylis-Hillman reaction. We successfully isolated the 25 types of Baylis-Hillman adducts using three different quinuclidine-supported ammonium-based ionic liquids such as Et3AmQ][BF4] (CATALYST-1), [Et3AmQ][PF6] (CATALYST-2), and [TMAAmEQ][NTf2](CATALYST-3) as new and efficient catalysts. Tedious and highly active N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide derivative was also synthesized using CATALYST-3 followed by Baylis-Hillman reaction. Generally, all the responses demonstrated higher activity and yielded high competition with various previously reported homogenous and heterogeneous Catalytic systems. Easy catalyst and product recovery followed by six catalysts recycling were the added advantages of the prosed catalytic system.
{"title":"Acceleration of Baylis-Hillman reaction using ionic liquid supported organocatalyst","authors":"V. Srivastava","doi":"10.2174/2213337208666210719100147","DOIUrl":"https://doi.org/10.2174/2213337208666210719100147","url":null,"abstract":"\u0000\u0000 Baylis-Hillman reaction suffers from the requirement of cheap starting materials, easy reaction protocol, possibility to create the chiral center in the reaction product has increased the synthetic efficacy of this reaction, and high catalyst loading, low reaction rate, and poor yield.\u0000\u0000\u0000\u0000\u0000 The extensive use of various functional or non-functional ionic liquids (ILs) with organocatalyst increases the reaction rate of various organic transformations as a reaction medium and as a support to anchor the catalysts. \u0000\u0000\u0000\u0000\u0000 In this manuscript, we have demonstrated the synthesis of quinuclidine-supported trimethylamine-based functionalized ionic liquid as a catalyst for the Baylis-Hillman reaction.\u0000\u0000\u0000\u0000\u0000We obtained the Baylis-Hillman adducts in good, isolated yield, low catalyst loading, short reaction time, broad substrate scope, accessible product, and catalyst recycling. N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide was also successfully synthesized using CATALYST-3 promoted Baylis-Hillman reaction.\u0000\u0000\u0000\u0000\u0000 We successfully isolated the 25 types of Baylis-Hillman adducts using three different quinuclidine-supported ammonium-based ionic liquids such as Et3AmQ][BF4] (CATALYST-1), [Et3AmQ][PF6] (CATALYST-2), and [TMAAmEQ][NTf2](CATALYST-3) as new and efficient catalysts. Tedious and highly active N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide derivative was also synthesized using CATALYST-3 followed by Baylis-Hillman reaction. Generally, all the responses demonstrated higher activity and yielded high competition with various previously reported homogenous and heterogeneous Catalytic systems. Easy catalyst and product recovery followed by six catalysts recycling were the added advantages of the prosed catalytic system.\u0000\u0000","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":" ","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43978631","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}
Pub Date : 2021-07-05DOI: 10.1515/9783110590050-002
Ierasia Triandafillidi, Errika Voutyritsa, C. Kokotos
{"title":"2 Recent advances in reactions promoted by amino acids and oligopeptides","authors":"Ierasia Triandafillidi, Errika Voutyritsa, C. Kokotos","doi":"10.1515/9783110590050-002","DOIUrl":"https://doi.org/10.1515/9783110590050-002","url":null,"abstract":"","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":"18 1","pages":""},"PeriodicalIF":1.1,"publicationDate":"2021-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79915987","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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