Pub Date : 2008-06-13DOI: 10.2174/1874095200802010068
Chengxia Miao, Jinquan Wang, Liang‐Nian He
Chemical fixation of CO2 has received much attention because CO2 is the most inexpensive and renewable carbon resource from the viewpoint of green chemistry and atom economy. The kinetic and thermodynamic stability of CO2 molecule presents significant challenges in designing efficient chemical transformations based on this potential feedstock. Currently, cyclic carbonates and polycarbonates are both valuable products, and the coupling of CO2 and epoxides is one of the most promising and eco-friendly methods for chemical conversion of CO2 into cyclic carbonates and/or polycarbonates. In this review, we will mainly discuss the synthesis of polycarbonates or cyclic carbonates catalyzed by metalsalen complexes through adjusting the architecture of the ligands and optimizing reaction conditions, such as temperature, pressure, co-catalysts, epoxide concentration. Furthermore, the recent progress for the synthesis of cyclic carbonates via the coupling reactions of epoxides and CO2 mediated by both homogeneous and heterogeneous catalysts is particularly reviewed.
{"title":"Catalytic Processes for Chemical Conversion of Carbon Dioxide into Cyclic Carbonates and Polycarbonates~!2008-03-31~!2008-04-14~!2008-06-10~!","authors":"Chengxia Miao, Jinquan Wang, Liang‐Nian He","doi":"10.2174/1874095200802010068","DOIUrl":"https://doi.org/10.2174/1874095200802010068","url":null,"abstract":"Chemical fixation of CO2 has received much attention because CO2 is the most inexpensive and renewable carbon resource from the viewpoint of green chemistry and atom economy. The kinetic and thermodynamic stability of CO2 molecule presents significant challenges in designing efficient chemical transformations based on this potential feedstock. Currently, cyclic carbonates and polycarbonates are both valuable products, and the coupling of CO2 and epoxides is one of the most promising and eco-friendly methods for chemical conversion of CO2 into cyclic carbonates and/or polycarbonates. In this review, we will mainly discuss the synthesis of polycarbonates or cyclic carbonates catalyzed by metalsalen complexes through adjusting the architecture of the ligands and optimizing reaction conditions, such as temperature, pressure, co-catalysts, epoxide concentration. Furthermore, the recent progress for the synthesis of cyclic carbonates via the coupling reactions of epoxides and CO2 mediated by both homogeneous and heterogeneous catalysts is particularly reviewed.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"5 1","pages":"68-82"},"PeriodicalIF":0.0,"publicationDate":"2008-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88186981","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 : 2008-06-10DOI: 10.2174/1874095200801020068
Chengxia Miao, Jinquan Wang, Liang‐Nian He
Chemical fixation of CO2 has received much attention because CO2 is the most inexpensive and renewable carbon resource from the viewpoint of green chemistry and atom economy. The kinetic and thermodynamic stability of CO2 molecule presents significant challenges in designing efficient chemical transformations based on this potential feedstock. Currently, cyclic carbonates and polycarbonates are both valuable products, and the coupling of CO2 and epoxides is one of the most promising and eco-friendly methods for chemical conversion of CO2 into cyclic carbonates and/or polycarbonates. In this review, we will mainly discuss the synthesis of polycarbonates or cyclic carbonates catalyzed by metalsalen complexes through adjusting the architecture of the ligands and optimizing reaction conditions, such as temperature, pressure, co-catalysts, epoxide concentration. Furthermore, the recent progress for the synthesis of cyclic carbonates via the coupling reactions of epoxides and CO2 mediated by both homogeneous and heterogeneous catalysts is particularly reviewed.
{"title":"Catalytic Processes for Chemical Conversion of Carbon Dioxide into Cyclic Carbonates and Polycarbonates","authors":"Chengxia Miao, Jinquan Wang, Liang‐Nian He","doi":"10.2174/1874095200801020068","DOIUrl":"https://doi.org/10.2174/1874095200801020068","url":null,"abstract":"Chemical fixation of CO2 has received much attention because CO2 is the most inexpensive and renewable carbon resource from the viewpoint of green chemistry and atom economy. The kinetic and thermodynamic stability of CO2 molecule presents significant challenges in designing efficient chemical transformations based on this potential feedstock. Currently, cyclic carbonates and polycarbonates are both valuable products, and the coupling of CO2 and epoxides is one of the most promising and eco-friendly methods for chemical conversion of CO2 into cyclic carbonates and/or polycarbonates. In this review, we will mainly discuss the synthesis of polycarbonates or cyclic carbonates catalyzed by metalsalen complexes through adjusting the architecture of the ligands and optimizing reaction conditions, such as temperature, pressure, co-catalysts, epoxide concentration. Furthermore, the recent progress for the synthesis of cyclic carbonates via the coupling reactions of epoxides and CO2 mediated by both homogeneous and heterogeneous catalysts is particularly reviewed.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"74 1","pages":"68-82"},"PeriodicalIF":0.0,"publicationDate":"2008-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79442913","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 : 2008-06-10DOI: 10.2174/1874095200801020065
I. Greiner, E. Hohmann, L. Vida, G. Keglevich
The coupling reaction of phenylboronic acid with 4-silyl-bromobenzenes incorporating an ionic liquid support or its neutral analogue at 80 °C in DMF/H2O in the presence of Pd(PPh3)4 and Na2CO3 takes place much faster and more efficiently under microwave irradiation than under traditional heating. It is an attractive method to carry out the generally slow Suzuki-Miyaura reactions under microwave conditions.
{"title":"Suzuki-Miyaura Reaction of 4-Silyl-bromobenzenes with Phenylboronic Acid under Thermal and Microwave Conditions","authors":"I. Greiner, E. Hohmann, L. Vida, G. Keglevich","doi":"10.2174/1874095200801020065","DOIUrl":"https://doi.org/10.2174/1874095200801020065","url":null,"abstract":"The coupling reaction of phenylboronic acid with 4-silyl-bromobenzenes incorporating an ionic liquid support or its neutral analogue at 80 °C in DMF/H2O in the presence of Pd(PPh3)4 and Na2CO3 takes place much faster and more efficiently under microwave irradiation than under traditional heating. It is an attractive method to carry out the generally slow Suzuki-Miyaura reactions under microwave conditions.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"40 1","pages":"65-67"},"PeriodicalIF":0.0,"publicationDate":"2008-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81226935","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 : 2008-06-09DOI: 10.2174/1874095200802010041
Margarita Alvira, S. Quinn, A. Aviñó, D. Fitzmaurice, R. Eritja
The preparation of oligonucleotide conjugates carrying viologen and fluorescein is described. Reaction of the appropriate carboxyl derivatives with oligonucleotides carrying aliphatic amino groups gave the desired compounds. A simple method for the introduction of the amino group at the 5'-end of the oligonucleotides is reported.
{"title":"Synthesis of oligonucleotide conjugates carrying viologen and fluorescent compounds","authors":"Margarita Alvira, S. Quinn, A. Aviñó, D. Fitzmaurice, R. Eritja","doi":"10.2174/1874095200802010041","DOIUrl":"https://doi.org/10.2174/1874095200802010041","url":null,"abstract":"The preparation of oligonucleotide conjugates carrying viologen and fluorescein is described. Reaction of the appropriate carboxyl derivatives with oligonucleotides carrying aliphatic amino groups gave the desired compounds. A simple method for the introduction of the amino group at the 5'-end of the oligonucleotides is reported.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"32 1","pages":"41-45"},"PeriodicalIF":0.0,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78497786","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 : 2008-06-09DOI: 10.2174/1874095200801020052
G. Shanbhag, K. Palraj, S. B. Halligudi
The hydroamination reaction offers a very attractive route for the synthesis of alkylated amines and their de- rivatives with no byproduct formation. Heterogeneous intermolecular hydroamination reactions of alkynes with aromatic amines using different inexpensive copper salts of hetropolyacid catalysts were investigated. Among heteropoly salts, copper salts of silicotungstic acid showed highest activity. Reactivity of aromatic amines increased with increase in its ba- sicity. Acidity in heterogeneous catalyst can act as promoter in hydroamination of alkynes.
{"title":"Hydroamination of Terminal Alkynes by Amines Catalyzed by Copper Heteropoly Salts: A Simple Approach Towards Imine Synthesis","authors":"G. Shanbhag, K. Palraj, S. B. Halligudi","doi":"10.2174/1874095200801020052","DOIUrl":"https://doi.org/10.2174/1874095200801020052","url":null,"abstract":"The hydroamination reaction offers a very attractive route for the synthesis of alkylated amines and their de- rivatives with no byproduct formation. Heterogeneous intermolecular hydroamination reactions of alkynes with aromatic amines using different inexpensive copper salts of hetropolyacid catalysts were investigated. Among heteropoly salts, copper salts of silicotungstic acid showed highest activity. Reactivity of aromatic amines increased with increase in its ba- sicity. Acidity in heterogeneous catalyst can act as promoter in hydroamination of alkynes.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"22 1","pages":"52-57"},"PeriodicalIF":0.0,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81464481","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 : 2008-06-09DOI: 10.2174/1874095200801020035
K. Elena, Klimova Tatiana, L. Irina, Domínguez Chávez Jorge, H. Simon, M. Daniel, Martínez-García Marcos
Symmetrical and asymmetrical cyclopropenones with diferrocenyl, diaryl and aryl-ferrocenyl substituents were obtained and their chemical behavior was studied. 1-Ethoxy-2,3-diarylcyclopropenylium terafluoroborate selectively reacts with MeLi, n-BuLi with formation of the 3,3-dialkyl-1,2-diarylcyclopropenes. The structures of 2,3-bis(4methoxyphenyl) cyclopropenone (10), 2-ferrocenyl-3-(4-methoxyphenyl) cyclopropenone (11), 2-ferrocenyl-3(naphthalen-1-yl) cyclopropenone (14) and 3,3-dimethyl-1,2-dianysol cyclopropene 19a were confirmed by X-ray crystallographic analysis.
{"title":"Symmetrical and Asymmetrical Cyclopropenones: Synthesis and Study of Their Chemical Reactivity","authors":"K. Elena, Klimova Tatiana, L. Irina, Domínguez Chávez Jorge, H. Simon, M. Daniel, Martínez-García Marcos","doi":"10.2174/1874095200801020035","DOIUrl":"https://doi.org/10.2174/1874095200801020035","url":null,"abstract":"Symmetrical and asymmetrical cyclopropenones with diferrocenyl, diaryl and aryl-ferrocenyl substituents were obtained and their chemical behavior was studied. 1-Ethoxy-2,3-diarylcyclopropenylium terafluoroborate selectively reacts with MeLi, n-BuLi with formation of the 3,3-dialkyl-1,2-diarylcyclopropenes. The structures of 2,3-bis(4methoxyphenyl) cyclopropenone (10), 2-ferrocenyl-3-(4-methoxyphenyl) cyclopropenone (11), 2-ferrocenyl-3(naphthalen-1-yl) cyclopropenone (14) and 3,3-dimethyl-1,2-dianysol cyclopropene 19a were confirmed by X-ray crystallographic analysis.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"1 1","pages":"35-40"},"PeriodicalIF":0.0,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83542115","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 : 2008-06-09DOI: 10.2174/1874095200801020046
D. Iga, Silvia Iga
Two isomeric partially acetylated galactocerebrosides, s-D-galactopyranosyl (2,3,4-tri-O-acetyl)- and s-D- galactopyranosyl (2,4,6-tri-O-acetyl)-1'(3'-O-acetyl)ceramide, were prepared from galactocerebroside and sulfatide, re- spectively. Their galactofuranosylation produced s-D-galactofuranosyl-6- and s-D-galactofuranosyl-3-s-D- galactopyranosyl-1'ceramide, as demonstrated by 1 H and 13 C NMR spectra as well as by chemical means. 1 H and 13 C NMR spectroscopy.
以半乳糖脑苷和硫脂分别制备了2种半乳糖脑苷同分异构体部分乙酰化的s-D-半乳糖脑苷(2,3,4-三- o -乙酰基)和s-D-半乳糖脑苷(2,4,6-三- o -乙酰基)-1′(3′- o -乙酰基)神经酰胺。他们的半乳糖呋喃基化产生了s- d -半乳糖呋喃基-6和s- d -半乳糖呋喃基-3-s- d -半乳糖吡喃基-1'神经酰胺，通过1h和13c核磁共振光谱以及化学方法证明。1h和13c核磁共振光谱。
{"title":"Galactofuranosylated Galactocerebrosides, a New Drug Delivery System for Ceramides to Colon","authors":"D. Iga, Silvia Iga","doi":"10.2174/1874095200801020046","DOIUrl":"https://doi.org/10.2174/1874095200801020046","url":null,"abstract":"Two isomeric partially acetylated galactocerebrosides, s-D-galactopyranosyl (2,3,4-tri-O-acetyl)- and s-D- galactopyranosyl (2,4,6-tri-O-acetyl)-1'(3'-O-acetyl)ceramide, were prepared from galactocerebroside and sulfatide, re- spectively. Their galactofuranosylation produced s-D-galactofuranosyl-6- and s-D-galactofuranosyl-3-s-D- galactopyranosyl-1'ceramide, as demonstrated by 1 H and 13 C NMR spectra as well as by chemical means. 1 H and 13 C NMR spectroscopy.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"1 1","pages":"46-51"},"PeriodicalIF":0.0,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80487559","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 : 2008-06-09DOI: 10.2174/1874095200802010058
Yanan Zhang, S. Handy
During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a re- versal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in re- gioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.
{"title":"A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters","authors":"Yanan Zhang, S. Handy","doi":"10.2174/1874095200802010058","DOIUrl":"https://doi.org/10.2174/1874095200802010058","url":null,"abstract":"During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a re- versal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in re- gioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"37 1","pages":"58-64"},"PeriodicalIF":0.0,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89652571","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 : 2008-04-22DOI: 10.2174/1874095200801020026
R. Abonía, Paola Cuervo, B. Insuasty, J. Quiroga, M. Nogueras, J. Cobo, H. Meier, E. Lotero
The commercially available Amberlyst ® -15 in the presence of AcOH was conveniently used to catalyze the in- tramolecular cyclization of a series of 2´-amino(1,3)dioxolochalcones to the corresponding dihydroquinolin-8-ones. This procedure is compatible with different functional groups and may be used as an alternative strategy for the synthesis of this important family of heterocyclic compounds.
{"title":"An Amberlyst-15® Mediated Synthesis of New Functionalized Dioxoloquinolinone Derivatives","authors":"R. Abonía, Paola Cuervo, B. Insuasty, J. Quiroga, M. Nogueras, J. Cobo, H. Meier, E. Lotero","doi":"10.2174/1874095200801020026","DOIUrl":"https://doi.org/10.2174/1874095200801020026","url":null,"abstract":"The commercially available Amberlyst ® -15 in the presence of AcOH was conveniently used to catalyze the in- tramolecular cyclization of a series of 2´-amino(1,3)dioxolochalcones to the corresponding dihydroquinolin-8-ones. This procedure is compatible with different functional groups and may be used as an alternative strategy for the synthesis of this important family of heterocyclic compounds.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"89 1","pages":"26-34"},"PeriodicalIF":0.0,"publicationDate":"2008-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74970167","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 : 2008-03-28DOI: 10.2174/1874095200801020017
S. Drioli, G. Bonora, M. Ballico
A new set of branched high-molecular weight multifunctional poly(ethylene glycol) (MultiPEG) derivatives was obtained from smaller commercial diOH-PEGs (M.W. = 2000 and 6000 Da) which were selectively monoprotected, properly activated at the residual OH-functions and treated with 1,3-diamino-2-propanol and 2-amino-1,3-propandiol as polyfunctional linkers. They were purified by molecular exclusion chromatography or extensive dialysis and characterized by GPC and 1 H-NMR. The final polymeric derivatives are characterized by a higher number of terminal reacting moieties (up to 6 times) than that found in linear, commercial PEGs of same molecular size. This increased loading capability can be applied to improve their use as drug carriers and soluble synthetic supports.
{"title":"New Syntheses of Branched, Multifunctional High-Molecular Weight Poly(ethylene glycol)s or (MultiPEG)s","authors":"S. Drioli, G. Bonora, M. Ballico","doi":"10.2174/1874095200801020017","DOIUrl":"https://doi.org/10.2174/1874095200801020017","url":null,"abstract":"A new set of branched high-molecular weight multifunctional poly(ethylene glycol) (MultiPEG) derivatives was obtained from smaller commercial diOH-PEGs (M.W. = 2000 and 6000 Da) which were selectively monoprotected, properly activated at the residual OH-functions and treated with 1,3-diamino-2-propanol and 2-amino-1,3-propandiol as polyfunctional linkers. They were purified by molecular exclusion chromatography or extensive dialysis and characterized by GPC and 1 H-NMR. The final polymeric derivatives are characterized by a higher number of terminal reacting moieties (up to 6 times) than that found in linear, commercial PEGs of same molecular size. This increased loading capability can be applied to improve their use as drug carriers and soluble synthetic supports.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"76 1","pages":"17-25"},"PeriodicalIF":0.0,"publicationDate":"2008-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73418662","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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