Nasra Hussein
Dr. Carolyn Wanamaker
CHE 222: Organic Chemistry 2
January 29, 2016
“Conversion of Oxazolidinediones to Isoindoloisoquinolinones via Intramolecular Friedel-Crafts Reaction” Researchers Ji-Young Min and Guncheol Kim from the Department of Chemistry at Chungnam National University developed a method of converting isoindoloisoquinolinones using a Friedel-Crafts reactions. Friedel-Crafts are reactions that involve a 2-step substitution mechanism where substituents are attached to aromatic rings. Two types of this reaction include alkylation and acylation. Alkylation involves the synthesis of alkylated products from reactions between aromatic rings and alkyl halides or alkenes. During this reaction the presence of a strong Lewis …show more content…
The reaction involves arenes and acyl chlorides or anhydrides. Interestingly, the reduction of acylation products can produce alkylation products. In this study, the chemists were interested in developing a new method of oxazolidine-4,5 to 3, -Aryl-3,4-dihydroisoquinolines. Researchers felt the older method was a long process which produced unattainable yields for the desired products. They wanted to develop a quicker reaction where aromatic compounds will go through a new transformation under Lewis acid catalysis and wanted to determine the best recipe for this reaction. This type of research was definitely a methodology. They begin to initiate a few changes in the procedure such as adding n-BuLi to solution, stirring for 3 h at 78 degrees Celsius, adding the Lewis acid catalyst AlCl3 at 0 degrees Celsius and warming mixture to room temp. All theses changes in protocol allowed for successful yields which were reproducible. The chemists also required for the aromatic ring to have electron-donating groups at the para and meta locations. The positioning of the electron-donating groups would allow for a adequately reactive aromatic ring, so when steric hindrance …show more content…
The acids tested included TSOH, SnCL4 , TiCl4 , BF3OEt2, AlCl3 , ZnCl2 and CF3COOH. The acids that provided the researchers with optimized condition was TiCl4 which allowed for a percent yield of 98% unlike AlCl3 which provided only 11% yield indicating possibly a longer reaction time especially during dione formation. The researchers also looked regiospecificity with the Lewis acids and they found that most acids except for TsOH were able to deliver a regiospecific manner. Observing their many attempts to produce the desired product and good yields gave a picture as to what was the recipe/requirement for this reaction to take place. All successful reactions had electron donating group on aromatic nucleophile, ideal reaction temperature was -40 degrees Celsius and meta substituted compounds provided higher yields. Also products that were considered to be a single isomer were due to regioselectivity which corresponded to their starting materials as well. Unsuccessful reactions include pyrrole and pyridine derivatives in which transformation did not appear. Products of the reaction were obtained via separation, washing and column chromatography. Products were analyzed by 1H and 13C NMR
Dr. Carolyn Wanamaker
CHE 222: Organic Chemistry 2
January 29, 2016
“Conversion of Oxazolidinediones to Isoindoloisoquinolinones via Intramolecular Friedel-Crafts Reaction” Researchers Ji-Young Min and Guncheol Kim from the Department of Chemistry at Chungnam National University developed a method of converting isoindoloisoquinolinones using a Friedel-Crafts reactions. Friedel-Crafts are reactions that involve a 2-step substitution mechanism where substituents are attached to aromatic rings. Two types of this reaction include alkylation and acylation. Alkylation involves the synthesis of alkylated products from reactions between aromatic rings and alkyl halides or alkenes. During this reaction the presence of a strong Lewis …show more content…
The reaction involves arenes and acyl chlorides or anhydrides. Interestingly, the reduction of acylation products can produce alkylation products. In this study, the chemists were interested in developing a new method of oxazolidine-4,5 to 3, -Aryl-3,4-dihydroisoquinolines. Researchers felt the older method was a long process which produced unattainable yields for the desired products. They wanted to develop a quicker reaction where aromatic compounds will go through a new transformation under Lewis acid catalysis and wanted to determine the best recipe for this reaction. This type of research was definitely a methodology. They begin to initiate a few changes in the procedure such as adding n-BuLi to solution, stirring for 3 h at 78 degrees Celsius, adding the Lewis acid catalyst AlCl3 at 0 degrees Celsius and warming mixture to room temp. All theses changes in protocol allowed for successful yields which were reproducible. The chemists also required for the aromatic ring to have electron-donating groups at the para and meta locations. The positioning of the electron-donating groups would allow for a adequately reactive aromatic ring, so when steric hindrance …show more content…
The acids tested included TSOH, SnCL4 , TiCl4 , BF3OEt2, AlCl3 , ZnCl2 and CF3COOH. The acids that provided the researchers with optimized condition was TiCl4 which allowed for a percent yield of 98% unlike AlCl3 which provided only 11% yield indicating possibly a longer reaction time especially during dione formation. The researchers also looked regiospecificity with the Lewis acids and they found that most acids except for TsOH were able to deliver a regiospecific manner. Observing their many attempts to produce the desired product and good yields gave a picture as to what was the recipe/requirement for this reaction to take place. All successful reactions had electron donating group on aromatic nucleophile, ideal reaction temperature was -40 degrees Celsius and meta substituted compounds provided higher yields. Also products that were considered to be a single isomer were due to regioselectivity which corresponded to their starting materials as well. Unsuccessful reactions include pyrrole and pyridine derivatives in which transformation did not appear. Products of the reaction were obtained via separation, washing and column chromatography. Products were analyzed by 1H and 13C NMR