cas 77-21-4, DL-Glutethimide | Articles data

Articles about 77-21-4Total 6 be found

Direct Deamination of Primary Amines via Isodiazene Intermediates
We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.
Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.
supporting information
p. 17366 - 17373
(2021/11/04)

Regiodivergent Copper Catalyzed Borocyanation of 1,3-Dienes
Copper catalyzed multi-functionalization of unsaturated carbon-carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4-borocupration and 4,1-borocupration of 1,3-dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2- or 4,3-borocyanation products.
Jia, Tao,He, Qiong,Ruscoe, Rebecca E.,Pulis, Alexander P.,Procter, David J.
p. 11305 - 11309
(2018/08/28)

Tert-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts
A transition metal-free direct arylation of 2-substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α-tolunitrile derivatives has been synthesized in good to excellent yields of 45-92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.
Qian, Xiaofei,Han, Jianwei,Wang, Limin
p. 940 - 946
(2016/04/05)

Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: Multicomponent synthesis of glutarimides
Mutual destruction of reagents in acid-and base-promoted reactions in the same container is now avoidable with the iridium polyhydride complex [IrH5(PiPr3)2] (1), which is an ambiphilic Lewis acid and base catalyst. By using catalyst 1, a three-component reaction of nitriles, olefins, and water proceeds efficiently to give glutarimides, which are pharmacologically important (see scheme).
Takaya, Hikaru,Yoshida, Kazunori,Isozaki, Katsuhiro,Terai, Hiroki,Murahashi, Shun-Ichi
p. 3302 - 3304
(2007/10/03)

An efficient synthesis of N-benzyl-3-sulfonyl glutarimides. Formal synthesis of the aromatase inhibitor AG-1
A formal [3+3] cycloaddition strategy to substituted glutarimides was studied. N-Benzyl α-sulfonylacetamides and various α,β-unsaturated esters were used as starting materials. (C) 2000 Elsevier Science Ltd.
Chang, Meng-Yang,Chang, Bo-Rui,Tai, Huo-Mu,Chang, Nein-Chen
p. 10273 - 10276
(2007/10/03)

Aromatase Inhibitors. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 3-Alkylated 3-(4-Aminophenyl)piperidine-2,6-diones
The synthesis and biological evaluation of 3-alkyl-substituted 3-(4-aminophenyl)piperidine-2,6-diones as inhibitors of estrogen biosynthesis are described .In vitro compounds 4-14 showed a stronger inhibition of human placental aromatase compared to aminoglutethimide (AG, compound 3), which recently has become used for the treatment of hormone-dependent breast cancer.The most active derivative, compound 10, showed a 93-fold stronger inhibition than AG.With the exception of 5, 7, and 8, all other compounds exhibited similar or decreased inhibition of bovine adrenal desmolase compared to AG.Compounds 4 and 6-12 showed a stronger inhibition of the plasma estradiol concentration of pregnant mare serum gonadotropin (PMSG) primed Sprague-Dawley (SD) rats compared to the parent compound.Compounds 4, 6-8, 10, and 12 inhibited the testosterone-stimulated tumor growth of ovariectomized 9,10-dimethyl-1,2-benzanthracene (DMBA) tumor-bearing SD rats more strongly than AG.Being stronger and more selective inhibitors of the estrogen biosynthesis than AG, some of the newly developed derivatives of AG might be better candidates for the treatment of the hormone-dependent human breast cancer.
Hartmann, Rolf W.,Batzl, Christine
p. 1362 - 1369
(2007/10/02)