4561-06-2Relevant articles and documents
Synthesis of novel isoindolone derivatives via cascade reactions. Contrasting diastereoselectivity under solution-phase vis-a-vis solvent-free ball-milling reaction conditions
Sánchez-Antonio, Omar,González-Olvera, Rodrigo,Aguilera-Cruz, Alejandro,Reyes-Ramírez, Adelfo,Juaristi, Eusebio
, (2019)
The highly diastereoselective synthesis, crystallographic analysis, and full characterization of several novel heterocycle-fused isoindolones is described. The synthetic strategy involves a cascade Michael/aldol-like cyclization reaction between N-substituted phthalimides rac-1 or 2 and several α,β-unsaturated electrophiles to afford the tricyclic systems pyrrolo[2,1- a]isoindolone and tetrahydropyrido[2,1-a]isoindolone. This synthetic strategy offers a convenient alternative to existing procedures for the preparation of isoindolone derivatives fused to five- and six-membered rings. X-ray crystallographic analysis allowed the determination of relative configurations and revealed that the synthesized compounds exhibit significant structural distortion, especially in the five membered rings. Relevantly, the diastereomeric distribution of products depends substantially on whether the cascade reaction is carried out under solution vis-a-vis solvent-free conditions.
Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams
Ding, Guangni,Li, Chengjun,Shen, Yifan,Lu, Bin,Zhang, Zhaoguo,Xie, Xiaomin
supporting information, p. 1241 - 1250 (2016/04/26)
Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity an
Efficient cesium carbonate promoted N-alkylations of aromatic cyclic imides under microwave irradiation
Escudero, Mercedes Isasmendi,Kremenchuzky, Lautaro D.,Perillo, Isabel A.,Cerecetto, Hugo,Blanco, Maria M.
experimental part, p. 571 - 576 (2011/04/15)
We present here an efficient and simple method for the N-alkylation of aromatic cyclic imides employing cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70 °C). The employment of microwave irradiation presents noteworthy advantages over conventional heating. The method is compatible with base labile functional groups. Georg Thieme Verlag Stuttgart - New York.
Highly efficient KF/Al2O3-catalyzed versatile hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds
Yang, Lei,Xu, Li-Wen,Xia, Chun-Gu
, p. 3279 - 3282 (2007/10/03)
The first example of KF/Al2O3-catalyzed versatile hetero-Michael addition reaction of nitrogen, oxygen, and sulfur nucleophiles was developed for facile preparation of organic compounds of widely different structures. In contrast with the existing methods using many acidic catalysts, this method is very general, simple, high-yielding, environmentally friendly, and oxygen and moisture tolerant.
SUBSTITUTED-4-THIAZOLIDINONE DERIVATIVES
-
, (2008/06/13)
Disclosed are novel substituted 4-thiazolidinone derivatives having cyclooxygenase and 5-lipoxygenase inhibiting properties and which are topical antiinflammatory agents for inflammed conditions of the skin
Photochemical and Thermal Transformations of O-Alkyl-S-phthalylalanyl Xanthates
Darji, R. R.,Shah, A.
, p. 104 - 106 (2007/10/02)
The reaction of phthalylalanyl chloride with different potassium O-alkylxanthates (R = Et, n-pr, iso-pr, n-Bu, iso-Bu) around 0 deg C in ether solution gave rise to the corresponding O-alkyl-S-phthalylalanyl xanthates.Irradiation of the latter in benzene solution gave xanthic acid disulphide, phthalylalanine and thioanhydride of phthalylalanine in addition to some other products.Thermal decomposition of these acylxanthates around 150 - 60 deg C for 15 - 20 min yielded the corresponding esters and carbon disulphide.
Hypolipidemic activity of phthalimide derivatives. 3. A comparison of phthalimide and 1,2-benzisothiazolin-3-one 1,1-dioxide derivatives to phthalimidine and 1,2-benzisothiazoline 1,1-dioxide congeners
Chapman Jr.,Cocolas,Hall
, p. 243 - 246 (2007/10/02)
Previously it has been observed that N-substituted phthalimide derivatives with chain lengths of four carbon or oxygen atoms showed potent hypolipidemic activity in rodents at 20 (mg/kg)/day ip. The 1,2-benzisothiazolin-3-one 1,1-dioxide (saccharin) nucleus, itself, had also been observed to be active at the same dose. An investigation was undertaken to examine a series of 1,2-benzisothiazolin-3-one 1,1-dioxide analogues for their hypolipidemic activity in mice and to compare them to their respective phthalimide congeners. In addition, a series of 1,2-benzisothiazoline 1,1-dioxide and phthalimidine analogues was prepared, and their hypolipidemic activity was compared to the phthalimide analogues. These studies show that the respective congeners of 1,2-benzisothiazolin-3-one 1,1-dioxide compared favorably to phthalimide congeners in reducing serum triglyceride and cholesterol levels in male CF1 mice at 20 (mg/kg)/day ip. Of the saccharin derivatives, 3-oxo-1,2-benzisothiazoline-2-propionic acid 1,1-dioxide was the most effective in lowering serum cholesterol levels by 53% after 16 days dosing and 3-oxo-1,2-dibenzothiazoline-2-valeric acid 1,1-dioxide lowered serum triglycerides 56% after 14 days dosing. The 1,2-benzisothiazoline 1,1-dioxide and phthalimidine compounds were less active as hypolipidemic agents than their 1,2-benzisothiazolin-3-one 1,1-dioxide and phthalimide analogues, respectively.
