5866-99-9Relevant academic research and scientific papers
Electrochemical oxidative cyclization of: N -allylcarboxamides: Efficient synthesis of halogenated oxazolines
He, Yanyang,Liu, Chenwei,Wu, Xiao-Feng,Yin, Yanzhao,Yin, Zhiping
supporting information, p. 663 - 667 (2022/01/22)
Herein, we reported an efficient and sustainable intramolecular electrochemical cyclization of N-allylcarboxamides for the synthesis of various halogenated oxazolines. This method was conducted in a simple undivided cell by employing lithium halogen salts
NOVEL VDAC1 INHIBITORS
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, (2022/02/07)
The present invention relates to a compound of general formula I Wherein R1-7, Hy, and X are as defined in claim 1. Such compound of formula I binds to VDAC1 and is suitable for use in a method for treating diabetes or pre-diabetes in a subject
Stereoselective Oxidative Cyclization ofN-Allyl Benzamides to Oxaz(ol)ines
Abazid, Ayham H.,Hollwedel, Tom-Niklas,Nachtsheim, Boris J.
supporting information, p. 5076 - 5080 (2021/07/19)
This study presents an enantioselective oxidative cyclization ofN-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besidesN-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-memberedN-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.
A CO2-Catalyzed Transamidation Reaction
Yang, Yang,Liu, Jian,Kamounah, Fadhil S.,Ciancaleoni, Gianluca,Lee, Ji-Woong
, p. 16867 - 16881 (2021/11/18)
Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2
Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
Baidya, Mrinmay,De Sarkar, Suman,Mahanty, Kingshuk,Maiti, Debabrata,Mallick, Samrat
supporting information, (2020/02/04)
The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).
Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
Zhang, Qing-Bao,Yuan, Pan-Feng,Kai, Liang-Lin,Liu, Kai,Ban, Yong-Liang,Wang, Xue-Yang,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 885 - 889 (2019/02/14)
The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group
Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes
Zheng, Jing,Deng, Ziyang,Zhang, Yan,Cui, Sunliang
supporting information, p. 746 - 751 (2016/03/09)
Most of the precedent copper-catalyzed trifluoromethylation reactions of unactivated alkenes concern terminal alkenes, and these processes are terminated in elimination, or nucleophilic addition, or semipinacol rearrangement, or C-H bond functionalization steps. In this study, we develop a trifluoromethylation method for both unactivated terminal and internal alkenes to enable divergent late-stage radical cyclization and achieve high molecular complexity. These cyclizations are well consistent with Baldwin's rule. Furthermore, a kinetic isotope effect (KIE) study and control reactions were conducted, and a plausible mechanism is proposed.
Iodoarene-catalyzed cyclizations of unsaturated amides
Alhalib, Ali,Kamouka, Somaia,Moran, Wesley J.
supporting information, p. 1453 - 1456 (2015/03/30)
The cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative conditions is presented. Five-, six-, and seven-membered rings with a range of substitutions can be prepared by this route. Preliminary data from the use of chiral iodoarenes as pr
POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.
Agwada
, p. 231 - 235 (2007/10/02)
The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.
