111861-29-1Relevant articles and documents
Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions
Zhu, Anlian,Li, Qixing,Feng, Wanlu,Fan, Dongshuang,Li, Lingjun
, p. 720 - 733 (2020/08/07)
Abstract: The synthesis of 2-amino-4H-chromenes through one-pot multicomponent reactions has received great attention due to the high atom efficiency and the broad bioactivities of the products. Here, the catalytic performances of a series of functional ionic liquids towards this type of reaction were investigated and the results showed that the ionic liquid, choline acetate ([Choline][Ac]), could efficiently promote this reactions under room temperature without the necessary of organic solvents. The reaction is easy to be conducted and the following work-up procedures are very simple. The pure products can be obtained through extraction and washing procedures, no column separation procedures are needed. Intriguingly, this reaction system can be easily scaled up to multi-gram, suggesting its perspective in industrial applications. In addition, the ionic liquid [Choline][Ac] can be easily prepared from cheap and biocompatible materials, and it can be feasibly recycled and reutilized for at least five cycles. Graphic Abstract: Various aldehydes, malononitrile and activated phenols could be converted to thecorresponding 2-amino-4H-chromenes with good to excellent isolated yields underthe catalysis of choline acetate at room temperature. [Figure not available: see fulltext.]
Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions
Zhu, Hai,Xu, Gang,Du, Huimin,Zhang, Chenlu,Ma, Ning,Zhang, Wenqin
, p. 217 - 229 (2019/05/16)
A series of new prolinamide polyacrylonitrile fiber catalysts with tunable length of alkyl linker and different linker group were prepared by covalent bonding for the first time and well characterized by mechanical strength, FT-IR, XRD, EA, TGA, SEM and water contact angel. The catalytic activities of these fiber catalysts were evaluated in Knoevenagel condensation and one-pot Knoevenagel-Michael multicomponent tandem reactions to synthesize α, β-unsaturated nitrile and 2-amino-4H-chromene derivatives in water. The result show that the suitable linker length attaching amines to fiber matrix as well as the constructed hydrophobic microenvironment by linker group within the surface layers of fiber materials effectively promotes the reactions. In addition, the good swollen capacity of fiber in solvent ensure that the reaction proceed well. Fiber catalyst PANPA?2F modified by prolinamide with a C2 alkyl chain exhibited the best catalytic performance and can be easily recovered and reused for at least ten consecutive cycles without significant loss of catalytic activity and active sites leaching.
Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene?D-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities
Thanh, Nguyen Dinh,Hai, Do Son,Ngoc Bich, Vu Thi,Thu Hien, Pham Thi,Ky Duyen, Nguyen Thi,Mai, Nguyen Thi,Dung, Tran Thi,Toan, Vu Ngoc,Kim Van, Hoàng Thi,Dang, Le Hai,Toan, Duong Ngoc,Thanh Van, Tran Thi
supporting information, p. 454 - 471 (2019/02/20)
The series of 2-amino-7-propargyloxy-4H-chromene-3-carbonitriles 5a-t were synthesized from corresponding 2-amino-7-phydroxy-4H-chromene-3-carbonitriles 4a-t and propargyl bromide. Two procedures were used in these syntheses: K2CO3/acetone and NaH/DMF procedures with yields of 65–89% and 80–96%, respectively. 1H-1,2,3-Triazole-tethered 4H-chromene?D-glucose conjugates 7a-t were synthesized using click chemistry of propargyl ethers 5a-t and tetra-O-acetyl-β-D-glucopyranosyl azide. Cu@MOF-5 was the optimal catalyst for this chemistry. The yields of 1H-1,2,3-triazoles were 80–97.8%. All triazoles 7a-t were evaluated in vitro for anti-microorganism activities. Among tested compounds with MIC values of 1.56–6.25 μM, there were four compounds against B. subtilis, four compounds against S. aureus, and four compounds against S. epidermidis; five compounds against E. coli, four compounds against K. pneumoniae, five compounds against P. aeruginosa, and six compounds against S. typhimurium. Compounds 7c,7d,7f,7h, and 7r had MIC values of 1.56–6.25 μM for three clinical MRSA isolates. Some compounds had inhibitory activities against four fungi, including A. niger, A. flavus, C. albicans, and S. cerevisiae, with MIC values of 1.56–6.25 μM. Some 1H-1,2,3-triazoles had comparatively low toxicity against RAW 264.7 cells.
