1515-72-6Relevant articles and documents
N-Alkylphthalimides: Structural requirement of thalidomidal action on 12-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor α production by human leukemia HL-60 cells
Shibata,Shichita,Sasaki,Nishimura,Hashimoto,Iwasaki
, p. 177 - 179 (1995)
Phthalimide analogs N-substituted with n-butyl, tert-butyl, hexyl and adamantyl groups were designed and prepared as simplified analogs of thalidomide and methylthalidomide. All the compounds prepared except N-n-butylphthalimide showed thalidomidal activity on 12-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor (TNF)-α production by human leukemia HL-60 cells. Among the investigated compounds, including thalidomide and methylthalidomide, N-adamantylphthalimide showed the most potent TNF-α production-enhancing activity.
Copper-catalyzed oxidation of arene-fused cyclic amines to cyclic imides
Yan, Xiaoyu,Fang, Kun,Liu, Hailan,Xi, Chanjuan
, p. 10650 - 10652 (2013)
A novel copper-catalyzed oxidation of arene-fused cyclic amines to the corresponding cyclic imides has been developed. The reaction can be used to synthesize 1,3-disubstituted TPD in high yields.
Carbonylative cyclization of o-halobenzoic acids for synthesis of N-substituted phthalimides using polymer-supported palladium-N-heterocyclic carbene as an efficient, heterogeneous, and reusable catalyst
Khedkar, Mayur V.,Khan, Shoeb R.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
, p. 2623 - 2629 (2012)
The carbonylative cyclization of o-iodobenzoic acid with a variety of primary amines and carbon monoxide (1 bar) using a polymer-supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as the catalyst gives N-substituted 1H-isoindole-1,3(2H)-diones (phthalimides) in good to excellent yields with a short reaction time. The catalyst is efficient, heterogeneous, and phosphine-free, it exhibited remarkable activity and it is also recyclable (4 consecutive cycles). The use of methyl o-iodobenzoate as the substrate under these conditions also gave N-substituted 1H-isoindole-1,3(2H)-diones, but with lower yields. Cyclization of o-iodobenzyl alcohol with carbon monoxide under these conditions gave isobenzofuran-1(3H)-one (phthalide). Georg Thieme Verlag Stuttgart · New York.
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
, p. 3768 - 3777 (2021/03/01)
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.