99855-94-4Relevant academic research and scientific papers
Visible-Light-Induced Meerwein Cascade Reactions for the Preparation of α-Aryl Esters
Niu, Teng-Fei,Li, Liang,Ni, Bang-Qing,Bu, Mei-Jie,Cai, Chun,Jiang, Hui-Liang
, p. 5775 - 5780 (2015/09/15)
A practical strategy has been developed for preparation of α-aryl ester derivatives by using a visible-light-induced Meerwein cascade reaction. This method uses molecular oxygen as an oxidant at room temperature without the need of hazardous reagents or harsh reaction conditions and provides a straightforward approach to pharmaceutically and synthetically useful α-aryl esters in moderate to good yields from simple and readily available starting materials. Oxindoles were also prepared by this protocol. A new strategy for the synthesis of α-aryl esters has been reported. This protocol utilizes acrylonitrile as a "bridge molecule" to combine a visible-light-induced Meerwein reaction and a hydrolysis reaction to generate α-aryl esters. This method was also employed for the preparation of oxindoles.
Experiments on the Chaperon effect in the nitration of aromatics
Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
, p. 952 - 958 (2007/10/03)
A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.
The potential application of catalytic antibodies to protecting group removal: Catalytic antibodies with broad substrate tolerance
Li,Hilton,Janda
, p. 2123 - 2127 (2007/10/02)
A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.
