126582-57-8Relevant academic research and scientific papers
An intermolecular Michael addition of benzene
Wang, Tai-Chi,Chen, Yeh-Long,Lee, Kuan-Han,Tzeng, Cherng-Chyi
, p. 6369 - 6370 (1996)
The first intermolecular Michael addition of benzene leading to the formation of 3,3-diphenylpropionanilide is described. 2-Methoxyaniline was reacted with cinnamoyl chloride to give 2-methoxycinnamanilide (1) which was treated with aluminum chloride in b
Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
Pandia, Biplab Keshari,Gunanathan, Chidambaram
, p. 9994 - 10005 (2021/07/31)
Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient C═C bond formation through aldol condensation. This selective olefination is facilitated by metal-ligand cooperation by the aromatization-dearomatization process operating in the catalytic system. Biorenewable alcohols are used as alkenylation reagents for the challenging α-alkenylation of amides with the highly abundant base metal manganese as a catalyst, which results in water and dihydrogen as the only byproduct, making this catalytic transformation attractive, sustainable, and environmentally benign.
An Efficient Solvent-Free Microwave-Assisted Synthesis of Cinnamamides by Amidation Reaction Using Phenylboronic Acid/Lewis Base Co-catalytic System
Carboni, Bertrand,Khaldoun, Khadidja,Safer, Abdelmounaim,Saidi-Besbes, Salima,Carreaux, Fran?ois,Le Guével, Rémy
, p. 3891 - 3900 (2019/10/11)
A microwave-assisted dehydrative amide condensation reaction is reported as an efficient access to cinnamamide derivatives under solvent-free conditions. This protocol between conjugated carboxylic acids and amines is based on the use of a co-catalytic system, including the presence of the commercially available phenylboronic acid and 4-(N, N-dimethylamino)pyridine N-oxide (DMAPO), with a complete chemoselectivity in favor of the corresponding α,β-unsaturated amides. The implementation of the reaction needs no special precaution, and less reactive amines, such as substituted anilines, are also efficient under these conditions. A series of novel conjugated amides have been evaluated for their cytotoxic activities against several human cancer cell lines.
Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors
Zhang, Mao,Lu, Xiang,Zhang, Hong-Jia,Li, Na,Xiao, Yu,Zhu, Hai-Liang,Ye, Yong-Hao
, p. 986 - 994 (2013/04/23)
A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 μM, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.
Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation with Boronic Acids, Aryl Diazonium Ions, and Ammonia
Ma, Yudao,Song, Chun,Chai, Qiang,Ma, Changqin,Andrus, Merritt B.
, p. 2886 - 2889 (2007/10/03)
Aryl diazonium tetrafluoroborates have been coupled with arylboron compounds, carbon monoxide, and ammonia to give aryl amides in high yields. A saturated N-heterocyclic carbene (NHC) ligand, H2IPr was used with palladium(II) acetate to give the active catalyst. A mechanism is proposed for this novel four-component coupling reaction.
Preparation of new 3-hydroxyquinoline alkaloid, jineol and its ether derivatives using directed ortho-lithiation of chloroquinoline as the key step
Tagawa, Yoshinobu,Yamashita, Hiroyuki,Nomura, Manami,Goto, Yoshinobu
, p. 2379 - 2387 (2007/10/03)
A new alkaloid, jineol (3,8-dihydroxyquinoline) was conveniently prepared employing directed ortho-lithiation of chloroquinoline for 3-position of quinoline ring. Moreover, the ether derivatives of jineol were obtained by the reaction of jineol with alkyl
Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction
Wang, Tai-Chi,Chen, Yeh-Long,Lee, Kuan-Han,Tzeng, Cherng-Chyi
, p. 87 - 90 (2007/10/03)
The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum (III) chloride in chlorobenzene at 120 °C or in benzene at 80 °C afforded exclusively 6-hydroxyquinolin-2(1H)-one (3a) or 4'-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum (III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.
AlCl3-mediated Regioselective Migration of a Methoxy Group of N-Methoxy-N-phenylamides to the ortho Position of the Phenyl Ring
Kikugawa, Yasuo,Shimada, Masahiro
, p. 1450 - 1451 (2007/10/02)
AlCl3-mediated decomposition of N-methoxy-N-phenylamides in dichloroethane leads to regioselective intramolecular migration of the methoxy group from the nitrogen to the ortho position of the phenyl ring via a tight ion pair intermediate.
