162333-02-0Relevant articles and documents
Intramolecular Pd-catalyzed reductive amination of enolizable sp3-C-H bonds
Ford, Russell L.,Alt, Isabel,Jana, Navendu,Driver, Tom G.
supporting information, p. 8827 - 8831 (2019/10/28)
A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C-NHAr bonds from sp3-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol ?% of Pd(OAc)2 and 10 mol ?% of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.
Synthesis of Aryl-Substituted 3,3a,4,5-Tetrahydropyrrolo[1,2- A [ quinolin-1(2 H)-ones and 2,3,4,4a,5,6-Hexahydro-1 H-pyrido[1,2- A [quinolin-1-ones
Watts, Field M.,Bunce, Richard A.
, p. 564 - 572 (2019/01/10)
A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- A nd 2,3,4,4a,5,6-hexahydro-1 H-pyrido[1,2- A [quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure affords the final lactam products. The reactions proceed cleanly and only two chromatographic purifications are required.
Design, synthesis, and pharmacological evaluation of fused β-homophenylalanine derivatives as potent DPP-4 inhibitors
Jiang, Tao,Zhou, Yuren,Chen, Zhuxi,Sun, Peng,Zhu, Jianming,Zhang, Qiang,Wang, Zhen,Shao, Qiang,Jiang, Xiangrui,Li, Bo,Chen, Kaixian,Jiang, Hualiang,Wang, Heyao,Zhu, Weiliang,Shen, Jingshan
supporting information, p. 602 - 606 (2015/05/27)
Dipeptidyl peptidase-4 (DPP-4) inhibitors are accepted as a favorable class of agents for the treatment of type 2 diabetes. Herein, a series of fused β-homophenylalanine derivatives as novel DPP-4 inhibitors were designed, synthesized, and evaluated for their inhibitory activities against DPP-4. Most of them displayed excellent DPP-4 inhibitory activities and good selectivity. Among them, 9aa, 18a, and 18m also showed good efficacy in an oral glucose tolerance test (OGTT) in ICR mice. Moreover, when dosed 8 h prior to glucose challenge, 18m showed significantly greater potency than sitagliptin. It thus provides potential candidates for the further development into potent drugs targeting DPP-4.
SPECIFIC ORTHO ORIENTATION IN THE VICARIOUS SUBSTITUTION OF HYDROGEN IN AROMATIC NITRO COMPOUNDS WITH CARBANION OF CHLOROMETHYL PHENYL SULFONE
Makosza, M.,Glinka, T.,Kinowski, A.
, p. 1863 - 1868 (2007/10/02)
Vicarious nucleophilic substitution of hydrogen atoms in nitroarenes with chloromethylphenyl sulfone proceeds selectively ortho to the nitro group when carried out in t-BuOK/THF base/solvent system.In the majority of 3-substituted nitrobenzene derivatives substitution occurs at the most hindered position 2.These conditions offer an efficient method of synthesis of 2,6 and 2,3-disubstituted nitrobenzene derivatives.
