68388-09-0Relevant academic research and scientific papers
tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides
Dai, Peng-Fei,Wang, Yi-Ping,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 9360 - 9364 (2021/12/09)
A synthetically practical transition metal/catalyst/halogen-free dehydrogenative coupling of aldehydes with N-hydroxyimides promoted solely by tert-butyl nitrite under mild conditions was developed. tert-Butyl nitrite generates two radicals (tBuO and NO) and thus works as a twofold hydrogen abstractor. A diverse array of N-hydroxyimide esters were prepared from either aliphatic or aromatic aldehydes. Benzoyl-substituted aldehydes such as 2-oxo-2-phenylacetaldehyde are also suitable.
N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation
Singh, Ashmita,Narula
supporting information, p. 7486 - 7490 (2021/05/13)
A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is
Discovery of IACS-9779 and IACS-70465 as Potent Inhibitors Targeting Indoleamine 2,3-Dioxygenase 1 (IDO1) Apoenzyme
Burke, Jason P.,Cross, Jason B.,Czako, Barbara,Hamilton, Matthew M.,Han, Michelle,Harris, Angela L.,Jiang, Yongying,Jones, Philip,Krapp, Stephan,Lammens, Alfred,Leonard, Paul G.,Lewis, Richard T.,Mandal, Pijus K.,Marszalek, Joseph R.,McAfoos, Timothy J.,Mikule, Keith,Mseeh, Faika,Parker, Connor A.,Petrocchi, Alessia,Pfaffinger, Dana,Reyna, Naphtali J.,Rogers, Norma E.,Soth, Michael J.,Theroff, Jay P.,Tremblay, Martin R.,Trevitt, Graham,Virgin-Downey, Brett,Wilcoxen, Keith,Xu, Alan,Yu, Simon S.
, p. 11302 - 11329 (2021/08/16)
Indoleamine 2,3-dioxygenase 1 (IDO1), a heme-containing enzyme that mediates the rate-limiting step in the metabolism of l-tryptophan to kynurenine, has been widely explored as a potential immunotherapeutic target in oncology. We developed a class of inhi
N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters
Singha, Krishnadipti,Ghosh, Subhash Ch.,Panda, Asit Baran
, p. 3205 - 3212 (2019/09/09)
Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.
A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation
Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
supporting information, p. 807 - 811 (2018/02/06)
In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.
COMPOUNDS USEFUL AS INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND/OR TRYPTOPHAN DIOXYGENASE
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Page/Page column 250, (2018/08/12)
Compounds of formula (VII), which are useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase, are provided. Also provided are pharmaceutical compositions, kits comprising said compounds, and methods and uses pertaining to said compounds.
Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N-hydroxyimides
Xu, Xiaohe,Li, Pingping,Huang, Yingyi,Tong, Chuo,Yan, YiYan,Xie, Yuanyuan
supporting information, p. 1742 - 1746 (2017/04/13)
Cross-dehydrogenative coupling (CDC) reactions of aldehydes with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI) under catalyst-free conditions is described. Moreover, the desired products can be obtained simply by recrystallization from ethanol. This method is also applicable to the synthesis of amides in excellent yields. A radical mechanism of the type shown in Scheme 4 is proposed based upon the inhibition of the reaction in the presence of TEMPO.
Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters
Xu, Xiaohe,Sun, Jian,Lin, Yuyan,Cheng, Jingya,Li, Pingping,Jiang, Xiaoying,Bai, Renren,Xie, Yuanyuan
supporting information, p. 7160 - 7166 (2017/12/28)
An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.
Metal-free intermolecular C-O cross-coupling reactions: Synthesis of: N -hydroxyimide esters
Lv, Yunhe,Sun, Kai,Pu, Weiya,Mao, Shukuan,Li, Gang,Niu, Jiejie,Chen, Qian,Wang, Tingting
, p. 93486 - 93490 (2016/10/21)
Selectfluor-mediated intermolecular C-O cross coupling reaction for the synthesis of N-hydroxyimide esters was developed for the first time. The reaction is applicable to the coupling of readily available aryl and alkyl aldehydes with N-hydroxyphthalimide (NHPI) and N-hydroxysuccinimide (NHSI). The resulting active esters can be directly converted into amides in one pot.
Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis
Dinda, Milan,Bose, Chandan,Ghosh, Tridev,Maity, Soumitra
, p. 44928 - 44932 (2015/06/02)
A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides has been developed for the synthesis of ester derivatives. Using 2 mol% [Ru(bpy)3]Cl2 in dry acetonitrile at room temperature with an LED light bulb, we were able to synthesize N-hydroxyesters in good yields. The ester derivatives are very useful synthetic intermediates, which were transformed to amide and oxazole building blocks in excellent yields. This journal is
