Melamine nitrate (MN) as a novel nitration reagent was easily prepared. Regioselective nitration of phenols to their corresponding o-nitrophenols occurred using MN with p-toluenesulfonic acid as catalyst in good to excellent yields. A distinct advantage of this method is the easy separation of products by simple filtration.
{"title":"Melamine Nitrate: A Novel and Efficient Reagent for Regioselective Nitration of Phenols","authors":"Yong-qiang Chen, Hong Jiang","doi":"10.1155/2011/753142","DOIUrl":"https://doi.org/10.1155/2011/753142","url":null,"abstract":"Melamine nitrate (MN) as a novel nitration reagent was easily prepared. Regioselective nitration of phenols to their corresponding o-nitrophenols occurred using MN with p-toluenesulfonic acid as catalyst in good to excellent yields. A distinct advantage of this method is the easy separation of products by simple filtration.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84501048","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}
The pilot plant study of cleaner production (CP) process of a dyes intermediate, Fast Bordeaux GP Base (2-nitro-p-anisidine), is presented in this work. The existing production process with acetic anhydride as raw material generates highly polluting (high chemical oxygen demand), huge-volume effluent, and thus the treatment is expensive. In the proposed process, raw material acetic anhydride in acetylation step is replaced with acetic acid. The reaction conditions like reaction time (3 h), temperature (120∘C) and molar ratio of p-anisidine and acetic acid (1 : 3.58) are optimized in the laboratory scale and implemented in pilot plant. The extent of conversion has been monitored by nitrite value test, and purity of product mixture is measured with thin-layer chromatography (TLC). The acidic wastewater quantity is dramatically reduced by incorporating recycling in washing scheme, and thus water consumption is reduced. Reduction in wastewater generation and reduction/elimination of treatment cost is also observed. Chemical oxygen demand (COD) of the effluent stream is reduced by the recovery of by-products sodium acetate and spent acid. The technoeconomical feasibility studies show that the proposed CP options are highly economical and environmental friendly.
{"title":"Cleaner Production Assessment of Fast Bordeaux GP Base","authors":"M. Mukhopadhyay, Rashmita Patel","doi":"10.1155/2011/752191","DOIUrl":"https://doi.org/10.1155/2011/752191","url":null,"abstract":"The pilot plant study of cleaner production (CP) process of a dyes intermediate, Fast Bordeaux GP Base (2-nitro-p-anisidine), is presented in this work. The existing production process with acetic anhydride as raw material generates highly polluting (high chemical oxygen demand), huge-volume effluent, and thus the treatment is expensive. In the proposed process, raw material acetic anhydride in acetylation step is replaced with acetic acid. The reaction conditions like reaction time (3 h), temperature (120∘C) and molar ratio of p-anisidine and acetic acid (1 : 3.58) are optimized in the laboratory scale and implemented in pilot plant. The extent of conversion has been monitored by nitrite value test, and purity of product mixture is measured with thin-layer chromatography (TLC). The acidic wastewater quantity is dramatically reduced by incorporating recycling in washing scheme, and thus water consumption is reduced. Reduction in wastewater generation and reduction/elimination of treatment cost is also observed. Chemical oxygen demand (COD) of the effluent stream is reduced by the recovery of by-products sodium acetate and spent acid. The technoeconomical feasibility studies show that the proposed CP options are highly economical and environmental friendly.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76880125","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 low-temperature redetermination by X-ray crystallography of four phenoxyalkanoic acid herbicides, 4-chloro-2-methylphenoxyacetic acid (MCPA), rac-2-(4-chloro-2-methylphenoxy)propionic acid (MCPP), 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-dichlorophenoxybutyric acid (2,4-DB), allowed the supramolecular structures of these compounds to be precisely described in terms of C⋯O/C–H⋯π interactions. The geometric parameters of the redetermined structures agree with those previously reported, but with improved precision.
{"title":"Crystal Packing and Supramolecular Motifs in Four Phenoxyalkanoic Acid Herbicides—Low-Temperature Redeterminations","authors":"L. Sieroń, J. Kobyłecka, A. Turek","doi":"10.1155/2011/608165","DOIUrl":"https://doi.org/10.1155/2011/608165","url":null,"abstract":"A low-temperature redetermination by X-ray crystallography of four phenoxyalkanoic acid herbicides, 4-chloro-2-methylphenoxyacetic acid (MCPA), rac-2-(4-chloro-2-methylphenoxy)propionic acid (MCPP), 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-dichlorophenoxybutyric acid (2,4-DB), allowed the supramolecular structures of these compounds to be precisely described in terms of C⋯O/C–H⋯π interactions. The geometric parameters of the redetermined structures agree with those previously reported, but with improved precision.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90961385","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}
The several aspects on the chemistry of eremanthine such as isolation, structural classification, biological activity, synthesis, and chemical transformations in other sesquiterpene lactones are described in this review. The main publications on this sesquiterpenolide, from its isolation of natural sources in 1972 to the current days, are included.
{"title":"A Review on the Chemistry of Eremanthine: A Sesquiterpene Lactone with Relevant Biological Activity","authors":"J. Alves","doi":"10.1155/2011/170196","DOIUrl":"https://doi.org/10.1155/2011/170196","url":null,"abstract":"The several aspects on the chemistry of eremanthine such as isolation, structural classification, biological activity, synthesis, and chemical transformations in other sesquiterpene lactones are described in this review. The main publications on this sesquiterpenolide, from its isolation of natural sources in 1972 to the current days, are included.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82053323","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}
M. Rajbangshi, M. R. Rohman, Icydora Kharkongor, Hormi Mecadon, B. Myrboh
Iodine-alumina was employed as a catalyst in the coupling reactions of aldehydes, enolizable ketones, or 1,3-dicarbonyls with methyl carbamate or aromatic amines under microwave irradiation to afford β-amino carbonyl compounds in good-to-excellent yields. The key features of this environmentally friendly methodology are its operational simplicity, mild reaction conditions, and less reaction time.
{"title":"Synthesis of β-Amino Carbonyl Compounds via the Iodine-Alumina Catalyzed Three-Component Coupling Reaction under Microwave Irradiation","authors":"M. Rajbangshi, M. R. Rohman, Icydora Kharkongor, Hormi Mecadon, B. Myrboh","doi":"10.1155/2011/514620","DOIUrl":"https://doi.org/10.1155/2011/514620","url":null,"abstract":"Iodine-alumina was employed as a catalyst in the coupling reactions of aldehydes, enolizable ketones, or 1,3-dicarbonyls with methyl carbamate or aromatic amines under microwave irradiation to afford β-amino carbonyl compounds in good-to-excellent yields. The key features of this environmentally friendly methodology are its operational simplicity, mild reaction conditions, and less reaction time.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77688691","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}
Anamika Sharma, Sonika Jain, R. Sirohi, D. Kishore
Synthesis of a new series of heteroaryl sulfones 6(a–f) in which the heteroaryl part is represented by acridine derivatives has been developed and reported here. The key step of this transformation involves the proton-catalyzed rearrangement of the sulphonamide derivatives 5(a–f) to the corresponding sulfones 6(a–f).
{"title":"Synthesis of [2′-(N-Ethylamino)-5′-Alkyl]phenyl-5,6,7,8-Tetrahydroacridine-9-Carboxy-2-Sulfone Derivatives by the Proton-Catalyzed Rearrangement of Corresponding Sulfonamides","authors":"Anamika Sharma, Sonika Jain, R. Sirohi, D. Kishore","doi":"10.1155/2011/614627","DOIUrl":"https://doi.org/10.1155/2011/614627","url":null,"abstract":"Synthesis of a new series of heteroaryl sulfones 6(a–f) in which the heteroaryl part is represented by acridine derivatives has been developed and reported here. The key step of this transformation involves the proton-catalyzed rearrangement of the sulphonamide derivatives 5(a–f) to the corresponding sulfones 6(a–f).","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81507964","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}
Treatment of a range of benzylic, allylic, and secondary aliphatic alcohols with potassium iodides in the presence of H4SiW12O40 affords the corresponding alkyl iodides in good to excellent yield with straightforward purification at room temperature in CH3CN.
{"title":"Tungstosilicic Acid: An Efficient and Ecofriendly Catalyst for the Conversion of Alcohols to Alkyl Iodides","authors":"M. Mokhtary, Faranak Najafizadeh","doi":"10.1155/2011/835183","DOIUrl":"https://doi.org/10.1155/2011/835183","url":null,"abstract":"Treatment of a range of benzylic, allylic, and secondary aliphatic alcohols with potassium iodides in the presence of H4SiW12O40 affords the corresponding alkyl iodides in good to excellent yield with straightforward purification at room temperature in CH3CN.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82722253","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}
K. Tabatabaeian, E. Keshavarz, M. Mamaghani, N. Mahmoodi
RuIII-catalyzed regio- and diastereoselective direct aldol reaction of progesterone with aromatic aldehydes has been developed in good yields (58–78%). Advantages of this method include catalytic efficiency, short reaction times, and ease of operation and workup.
{"title":"RuCl3 · nH2O as Catalyst for Diastereoselective Direct Aldol Reaction: An Efficient Route to Hormone Steroid Derivatives","authors":"K. Tabatabaeian, E. Keshavarz, M. Mamaghani, N. Mahmoodi","doi":"10.1155/2011/325291","DOIUrl":"https://doi.org/10.1155/2011/325291","url":null,"abstract":"RuIII-catalyzed regio- and diastereoselective direct aldol reaction of progesterone with aromatic aldehydes has been developed in good yields (58–78%). Advantages of this method include catalytic efficiency, short reaction times, and ease of operation and workup.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84182465","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}
M. Messali, M. Abboudi, M. Aouad, N. Rezki, E. Christiaens
The discovery of the antioxidant activity of selenoenzyme glutathione peroxidase (GPx) has attracted growing attention in the biochemistry of selenium. Among molecules which mimic the structure of the active site of the enzyme, N-phenyl-1,2-benzisoselenazolin-3-one 1, Ebselen, exhibited useful anti-inflammatory properties. It has been extensively investigated and has undergone clinical trials as an anti-inflammatory agent. Unfortunately, Ebselen exhibits relatively poor catalytic activity, prompting attempts to design more efficacious GPx mimetics that would retain his low toxicity while manifesting improved catalytic properties. In this context, novel 1,2-benzoselenazine and 1,2-benzoselenazols, which are five and six membered homologues of Ebselen were synthesized and characterized. One structure has been proven by single crystal X-ray crystallography.
{"title":"Synthesis and Characterization of a New Five and Six Membered Selenoheterocyclic Compounds Homologues of Ebselen","authors":"M. Messali, M. Abboudi, M. Aouad, N. Rezki, E. Christiaens","doi":"10.1155/2011/389615","DOIUrl":"https://doi.org/10.1155/2011/389615","url":null,"abstract":"The discovery of the antioxidant activity of selenoenzyme glutathione peroxidase (GPx) has attracted growing attention in the biochemistry of selenium. Among molecules which mimic the structure of the active site of the enzyme, N-phenyl-1,2-benzisoselenazolin-3-one 1, Ebselen, exhibited useful anti-inflammatory properties. It has been extensively investigated and has undergone clinical trials as an anti-inflammatory agent. Unfortunately, Ebselen exhibits relatively poor catalytic activity, prompting attempts to design more efficacious GPx mimetics that would retain his low toxicity while manifesting improved catalytic properties. In this context, novel 1,2-benzoselenazine and 1,2-benzoselenazols, which are five and six membered homologues of Ebselen were synthesized and characterized. One structure has been proven by single crystal X-ray crystallography.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89948887","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 new series of 2-{4-[2-(N-methyl-2-pyridylamino)ethoxy]phenyl}-5-substituted 1,3,4-oxadiazoles were synthesized by the oxidative cyclization of hydrazones derived from 4-[2-(methylpyridin-2-ylamino)ethoxy]benzaldehyde and aryl hydrazines using chloramine-T as an efficient catalyst. All steps were assisted by microwave irradiation. Microwave enables all these reactions to be simple, rapid, high yielding, and avoid chromatograph purification and led environmentally benign total synthesis of focused oxadiazole library. All the synthesized compounds were isolated in good yield and characterized by 1H NMR, 13C NMR, and elemental analyses. The title compounds represent a novel class of biologically active heterocycles.
{"title":"Microwave-Assisted Solution Phase Synthesis of Novel 2-{4-[2-(N-Methyl-2-pyridylamino)ethoxy]phenyl}-5-Substituted 1,3,4-Oxadiazole Library","authors":"S. Gaonkar, Izuru Nagashima, H. Shimizu","doi":"10.1155/2011/751894","DOIUrl":"https://doi.org/10.1155/2011/751894","url":null,"abstract":"A new series of 2-{4-[2-(N-methyl-2-pyridylamino)ethoxy]phenyl}-5-substituted 1,3,4-oxadiazoles were synthesized by the oxidative cyclization of hydrazones derived from 4-[2-(methylpyridin-2-ylamino)ethoxy]benzaldehyde and aryl hydrazines using chloramine-T as an efficient catalyst. All steps were assisted by microwave irradiation. Microwave enables all these reactions to be simple, rapid, high yielding, and avoid chromatograph purification and led environmentally benign total synthesis of focused oxadiazole library. All the synthesized compounds were isolated in good yield and characterized by 1H NMR, 13C NMR, and elemental analyses. The title compounds represent a novel class of biologically active heterocycles.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2011-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78987896","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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