37831-25-7Relevant academic research and scientific papers
Acid-catalyzed chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines
Guo, Luxia,Chen, Zihao,Zhu, Hongmei,Li, Minghao,Gu, Yanlong
supporting information, p. 1419 - 1422 (2020/11/12)
Chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines were described, which were established on the basis of either a C[sbnd]C bond cleavage or a rearrangement process of a reaction intermediate. These reactions proceeded in a condition-determined manner with good functional group tolerance. In the first model, 2,2-dimethoxyacetaldehyde reacted with aniline to form a new C[sbnd]N bond, in the presence of O2, via a C[sbnd]C bond cleavage reaction. However, in the second model, by performing the reaction in the absence of O2, Heyns rearrangement occurred and generated a new C[sbnd]O bond to form methyl phenylglycinate. Such condition-determined reactions not only offered the new way for value-added conversion of biomass-derived platform molecule, 2, 2-dimethoxyacetaldehyde, but also provided efficient methods for the synthesis of N-arylformamides and methyl phenylglycinates.
FUSED PYRIMIDINE PYRIDINONE COMPOUNDS AS JAK INHIBITORS
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Page/Page column 69, (2021/06/04)
The disclosure provides compounds of formula (I), or a pharmaceutically-acceptable salt thereof, wherein the variables are defined in the specification, that are inhibitors of JAK kinases, particularly JAK3. The disclosure also provides pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat gastrointestinal inflammatory diseases.
HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media
Dhawan, Sanjeev,Girase, Pankaj Sanjay,Kumar, Vishal,Karpoormath, Rajshekhar
, p. 3729 - 3739 (2021/10/14)
We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups.
Cobalt nanoparticles anchoring on nitrogen doped carbon with excellent performances for transfer hydrogenation of nitrocompounds to primary amines and N-substituted formamides with formic acid
Zhang, Yuecheng,Cao, Pengwei,Zhang, Hong-Yu,Yin, Guohui,Zhao, Jiquan
, (2019/07/08)
Cobalt nanoparticles anchoring on nitrogen doped carbon derived from pyrolysis of a cobalt complex and chitosan were developed for reduction of nitrocompounds with neat formic acid to their corresponding amines or N-substituted formamides by switch of solvents. Characterization results revealed that most of the nitrogen atoms are present as graphitic N and pyridinic N as anchoring sites, and the cobalt nanoparticles are wrapped by nitrogen doped carbon layers, endowing the catalyst with excellent activity and superior reusability.
KOtBu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
Ghosh, Tridev,Jana, Snehasish,Dash, Jyotirmayee
supporting information, p. 6690 - 6694 (2019/09/12)
This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.
Mild and facile synthesis of formamide: Reduction and functionalization of CO2 using NaBH(OAc)3 under atmospheric pressure
Liu, Huan,Nie, Zhuang,Shao, Jiaan,Chen, Wenteng,Yu, Yongping
supporting information, p. 3552 - 3555 (2019/07/09)
An approach for N-formylation of amines was developed using NaBH(OAc)3 as a reductant under an atmospheric pressure of CO2 at 50 °C. The corresponding formylated products of various amines, including aliphatic and aromatic amines, amines with reductive-sensitive nitro groups and alkynyl groups and benzamides were obtained in good to excellent yields, and the possible reaction mechanism was also proposed.
An efficient method for the N-formylation of amines under catalyst- and additive-free conditions
Xu, Zhuo-Wei,Xu, Wen-Yi,Pei, Xiao-Jun,Tang, Fei,Feng, Yi-Si
supporting information, p. 1254 - 1258 (2019/04/10)
A simple catalyst- and additive-free method for the N-formylation of amines has been developed. The advantages of this protocol include a wide range of functional group tolerance, high efficiency and a lack of required extra promoters under mild conditions. This convenient strategy will provide a facile synthesis towards N-formamide natural products and pharmaceutical derivatives. A mechanism that involves difluorocarbene is proposed for this reaction.
One-pot photocalalytic reductive formylation of nitroarenes via multielectron transfer by carbon nitride in functional eutectic medium
Markushyna, Yevheniia,V?lkel, Antje,Savateev, Aleksandr,Antonietti, Markus,Filonenko, Svitlana
, p. 186 - 194 (2019/11/26)
In the past years organic semiconductor photocatalysis has made the remarkable advances in developing efficient synthetic chemical routes to well refined structures. Until now, most efforts were focused on optimizing of the semiconductor photocatalyst, while solvents were largely ignored. Herein, we design a series of functional deep eutectic solvents (DES) with adjustable physicochemical properties – density, viscosity, glass transition temperature, and chemical activity towards reductive formylation of nitroarenes. The DES are prepared from abundant, sustainable resources, which makes them an affordable alternative to the ionic liquids, even on larger industrial scales. By combining the ammonium formate-based DES with carbon nitride photocatalyst, we enable the simultaneous six-electron reduction of nitro-compounds to the corresponding N-substituted formamides and benzimidazoles in one pot.
Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions
Jia, Mengmeng,Zhang, Heng,Lin, Yongjia,Chen, Dimei,Chen, Yanmei,Xia, Yuanzhi
, p. 3615 - 3624 (2018/05/26)
The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.
One-pot selective N-formylation of nitroarenes to formamides catalyzed by core-shell structured cobalt nanoparticles
Dong, Xiaosu,Wang, Zhaozhan,Duan, Yanan,Yang, Yong
supporting information, p. 8913 - 8916 (2018/08/17)
One-pot direct N-formylation of readily available nitroarenes with ammonium formate catalyzed by core-shell structured cobalt nanoparticles has been developed. A broad set of nitroarenes was successfully converted to their corresponding formamides in good to high yields with various functional group tolerance. This heterogeneous catalyst can be easily removed from the reaction medium and can be reused several times without a significant loss of reaction efficiency.
