138306-33-9Relevant academic research and scientific papers
Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides
Sasiambarrena, Leandro D.,Barri, Ivan A.,Fraga, Guido G.,Bravo, Rodolfo D.,Ponzinibbio, Agustín
supporting information, p. 264 - 267 (2019/01/04)
A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.
Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction
Chizhova, Maria,Khoroshilova, Olesya,Dar'In, Dmitry,Krasavin, Mikhail
, p. 12722 - 12733 (2018/10/15)
In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.
Quinazolinones, Quinazolinthiones, and Quinazolinimines as Nitric Oxide Synthase Inhibitors: Synthetic Study and Biological Evaluation
Camacho, M. Encarnación,Chayah, Mariem,García, M. Esther,Fernández-Sáez, Nerea,Arias, Fabio,Gallo, Miguel A.,Carrión, M. Dora
, p. 638 - 650 (2016/08/27)
The synthesis of different compounds with a quinazolinone, quinazolinthione, or quinazolinimine skeleton and their in vitro biological evaluation as inhibitors of inducible and neuronal nitric oxide synthase (iNOS and nNOS) isoforms are described. These d
Preparation of benzolactams by Pd(OAC)2-catalyzed direct aromatic carbonylation
Orito, Kazuhiko,Horibata, Akiyoshi,Nakamura, Takatoshi,Ushito, Harumi,Nagasaki, Hideo,Yuguchi, Motoki,Yamashita, Satoshi,Tokuda, Masao
, p. 14342 - 14343 (2007/10/03)
We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary ω-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines. Copyright
Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives
Akazome, Motohiro,Kondo, Teruyuki,Watanabe, Yoshihisa
, p. 3375 - 3380 (2007/10/02)
The dichlorobis(triphenylphosphine)palladium (PdCl2(PPh3)2)-tin(II)chloride (SnCl2) system shows high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 deg C for 16 h under 20 kg cm-2 of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in good yield.For example, 2-phenylindole was obtained in 75percent yield from the reductive N-heterocyclization of 2-nitrostilbene.Similarly, 2-propyl-2H-indazole was readily prepared in 83percent yield by the reductive N-heterocyclization of N-(2-nitrobenzylidene)propylamine.A nitrene intermediate for the present reaction is proposed on the basis of deuterium-labeling experiments and the investigation of alkyl rearrangement in the construction of the indole skeleton.Carbon monoxide effectively operates as a deoxygenating agent of the nitro group to afford a nitrene intermediate.
