Article
Polymer Science
Hao Fu, Linbo Gong, Shuling Gong
Summary: In this study, a self-dispersible, non-ionic waterborne comb-like polyester (NWCPE) was successfully synthesized by grafting an amino-terminated hydrophilic polyether to a series of linear polyesters using a facile and mild aza-Michael addition. The NWCPE dispersion showed excellent storage stability and hydrolysis resistance, and the cross-linked film exhibited good water resistance and mechanical properties.
Article
Chemistry, Applied
Fushuai Li, Zhihong Yang, Yanyan Yang, Qiuhong Huang, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Summary: A chiral phosphorus acid catalyzed enantioselective 1,4-conjugate addition of arylamines to in situ formed 7-methylene-7H-indoles from 7-indolylmethanols has been successfully developed for the first time without the use of additives. The catalytic protocol enables the formation of 1,4-adducts with a nitrogen-containing tertiary carbon stereocenter in moderate to high yields and good enantioselectivity under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Materials Science, Multidisciplinary
Witsanu Sombat, Panassilp Authai, Panuwat Padungros, Voravee P. Hoven
Summary: Micellar systems have been recognized as effective nanoreactors for performing chemical reactions in aqueous solutions. This research developed nanoreactors from polymeric micelles, in which organic substrates were encapsulated and stabilized. The micellar nanoparticles assembled from PBAM-ran-PHPAM were spherical and well-dispersed in water, with a diameter of less than 170 nm. Thia-Michael addition reactions in the presence of the PBAM26-ran-PHPAM copolymer resulted in high conversions and isolated yields of the Michael adducts. The micellar nanoreactors were also reusable up to 10 times with a high reaction conversion of 75%.
ACS APPLIED POLYMER MATERIALS
(2023)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Applied
Andrea Guerrero-Corella, Miguel A. Valle-Amores, Alberto Fraile, Jose Aleman
Summary: An asymmetric organocatalytic aza-Michael addition reaction of ketimines to nitroolefins is described, utilizing 2-hydroxybenzophenone imine to improve the enantioselective addition of N-centered nucleophiles to nitroalkenes. The versatility of the process is demonstrated under both batch and flow conditions, resulting in the synthesis of a wide variety of nitroamine derivatives with excellent yields and enantioselectivities. Additionally, this methodology was successfully applied to the formal synthesis of VNI, a drug-like scaffold for the treatment of Chagas disease.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jyotirmoy Ghosh, Joshua Mendoza, R. Graham Cooks
Summary: The sulfur fluoride exchange (SuFEx) reaction is of great significance in drug discovery, materials science, and chemical biology. In this study, the SuFEx reaction was successfully accelerated by microdroplet reaction and the reaction scope was determined. Additionally, the study demonstrated the value of microdroplet-assisted accelerated reactions combined with high-throughput experimentation for characterization of reaction scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Zoran Glasovac, Luka Baresic, Davor Margetic
Summary: The reaction mechanism of guanidinium chlorides with dimethyl acetylenedicarboxylate in a aza-Michael addition reaction/intramolecular cyclization was investigated using DFT M06-2X and B3LYP computational approaches. The energies of the products were compared with experimental data or product ratios obtained from other methods. The diversity of the products was explained by the formation of different tautomers upon deprotonation. The initial nucleophilic addition was found to be the most energetically demanding step, and the overall reaction was exergonic due to methanol elimination during cyclization.
Article
Materials Science, Multidisciplinary
Lucile Fauvre, Etienne Fleury, Francois Ganachaud, Daniel Portinha
Summary: Silicone elastomers with self-associating bisamide groups were synthesized using aza-Michael addition. Non-crosslinked copolymers were prepared by adjusting the molar ratio of vinyl to primary amine reactive function. By increasing the molecular weight, the copolymers transformed from viscoelastic liquids to viscoelastic solids and elastomers.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Organic
Rupashri Dash, Sudhir Kumar Hota, Sandip Murarka
Summary: We describe an efficient higher order conjugate addition reaction of azauracils to substituted para-quinone methides (p-QMs) mediated by triethylamine, forming previously unknown diarylmethane scaffolds through C-N bond formation. This protocol offers mild conditions, high atom economy, broad scope, and allows convenient access to biologically relevant new chemical entities (NCEs) consisting of p-QM and azauracil hybrids in good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Samiran Bhattacharjee, Aftab Ali Shaikh, Wha-Seung Ahn
Summary: CuBTC was found to be an effective heterogeneous catalyst for the aza-Michael addition reaction of various amines to electron deficient alkenes at room temperature, providing high product yields and selectivity. While cyclic and aliphatic amines showed high yields within a short reaction time, aromatic amines exhibited slower reaction rates and lower yields. The catalyst could be reused multiple times without losing activity, and XRD and SEM analysis confirmed the retention of catalyst crystallinity during the reaction.
Article
Polymer Science
Junyi Zhou, Xavier Allonas, Xiaoxuan Liu, Shanghua Wu
Summary: In the process of free radical UV curing, the surface of cured materials often retains a significant amount of acryl groups due to oxygen inhibition. These acryl groups can be utilized for surface modification through aza-Michael addition reactions. By using various amino compounds, the hydrophilicity and affinity of oxygen-inhibited surfaces can be improved, leading to diverse surface properties after modification.
POLYMER INTERNATIONAL
(2021)
Article
Biochemistry & Molecular Biology
Alper Yildirim, Ufuk Atmaca, Ertan Sahin, Parham Taslimi, Tugba Taskin-Tok, Murat Celik, Ilhami Gulcin
Summary: This article examines the use of oxazolidinones in various applications such as antibiotics and protein synthesis inhibition. The synthesized compounds were found to have potent inhibitory effects on enzymes such as acetylcholinesterase and carbonic anhydrase. Molecular docking and ADMET analysis were conducted to correlate the experimental data.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Article
Biochemistry & Molecular Biology
Jian-Qiang Zhao, Wen-Jie Wang, Shun Zhou, Qi-Lin Xiao, Xi-Sha Xue, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Wei-Cheng Yuan
Summary: An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments.
Article
Chemistry, Physical
Md Mushtaque, Fernando Avecilla, Irfan Ahmad, Ahmed M. Alharbi, Parvez Khan, Shahzaib Ahamad, Md Imtaiyaz Hassan
Summary: A new 5-fluorouracil derivative (3) obtained through Aza-Michael addition reaction exhibits high selectivity and inhibition potential towards carbonic anhydrase IX, with a high binding affinity and greater efficacy in reducing cancer cell viability under hypoxic conditions. Molecular docking and simulation studies support its potential as a lead molecule for synthesizing anticancer compounds.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Polymer Science
Paige A. Shaw, Maxime Klausen, Mark Bradley
Summary: A light-responsive polymer capable of controlled release of camptothecin and generation of reactive oxygen species (ROS) was developed, which exhibited high cancer cell killing activity through both camptothecin release and ROS generation.
Article
Polymer Science
Donghui Zhang, Shiqi Liu, Zhihao Cai, Weizhe Luo, Guojian Liu, Runhui Liu
Summary: A straightforward and efficient method for synthesizing NPC monomers has been developed in this study, which enhances the availability of NPC monomers and facilitates the synthesis of polypeptides.
