93099-45-7Relevant academic research and scientific papers
Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles
Panda, Niranjan,Sahoo, Kanchanbala
supporting information, (2022/02/03)
Iron(III) chloride mediated para-selective C?H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole b
Iron(III)-Mediated Nucleophilic Halogenation of Phenols Using an Amido Directing Group
Guo, Dou,Liu, Yibo,Lu, Dongbiao,Lu, Yufan,Meng, Wei,Wan, Congcong,Wang, Hongling,Yang, Hongxiang,Yuan, Ye,Zhang, Xiang
, (2022/05/20)
A regioselective and nucleophilic halogenation of electron-rich amidophenols was realized in the presence of Fe(III) reagents and amido-directing groups. Halides could be sequentially introduced to specific positions to form mono-, di- and mixed di- halogenated amidophenols. Furthermore, this protocol provides new methods for the syntheses of IKK2 inhibitor (IMD-0354), muscle relaxant (Chlorzoxazone) and related derivatives.
N-(2-hydroxyaryl)benzamide synthesis from 2-nitroaryl benzoates via an Indium-mediated reduction-migration reaction
Lee, Hyejeong,Kim, Minki,Jun, Young Moo,Kim, Byeong Hyo,Lee, Byung Min
experimental part, p. 158 - 167 (2011/10/08)
A one-pot reduction-triggered N-(2-hydroxyaryl)benzamide synthesis from 2-nitroaryl benzoate substrates was investigated. In the presence of indium/AcOH in THF/H2O, 2-nitroaryl benzoates produced reasonable yields of the benzo group migrated N-
Structural modifications of benzanilide derivatives, effective potassium channel openers. X.
Calderone, Vincenzo,Coi, Alessio,Fiamingo, Francesca Lidia,Giorgi, Irene,Leonardi, Michele,Livi, Oreste,Martelli, Alma,Martinotti, Enrica
, p. 1421 - 1429 (2007/10/03)
Large-conductance calcium-activated potassium (BK) channels are involved in many fundamental cell functions. Consistently, the ability to activate BK channels by exogenous compounds is considered as a promising pharmacodynamic pattern for the potential treatment of several pathologies. In this perspective, the development of new and selective BK-openers can be considered as an actual field of research. This paper reports the synthesis and pharmacological evaluation of new benzanilides, useful for deepening the comprehension of the structure-activity relationships, emerged in previous studies on this class of BK-activators. From a structural point of view, these benzanilides belong to a general class of BK-activators, showing a common pharmacophoric model, consisting of two aryl groups linked through an appropriate "spacer" and the almost obligatory presence of a phenolic hydroxyl. In particular, a new series of benzanilides, in which the phenyl rings have been widely changed both on the acidic portion and the basic one of the amide spacer, were synthesised. Their vasorelaxing effects, induced through the activation of BK channels, were also evaluated. Although many compounds exhibited effects which could not be attributed to the activation of BK channels, two derivatives showed a clear profile of BK-activators with vasodilator activity comparable to or slightly lower than that recorded for the reference benzimidazolone NS1619. A further molecular modelling approach allowed us to obtain a molecular electrostatic potential feature which suggests a suitable interaction with the receptor site of the BK channel, from a tri-dimensional point of view. This approach seems to represent a further contribution for the development of new BK-activators, designed on the basis of the pharmacophoric model above-mentioned.
AlCl3-mediated migration of benzamido group of N-phenoxybenzamide derivatives to the phenyl group
Miyazawa, Etsuko,Sakamoto, Takeshi,Kikugawa, Yasuo
, p. 7 - 12 (2007/10/03)
AlCl3-mediated decomposition of N-phenoxybenzamide derivatives in dichloromethane mainly leads to regioselective intramolecular migration of benzamido group from the oxygen to the ortho position of the phenyl group via electron-deficient nitrogen intermediates.
Synthesis of 2-Arylbenzoxazoles via the Palladium-Catalyzed Carbonylation and Condensation of Aromatic Halides and o-Aminophenols
Perry, Robert J.,Wilson, B. David,Miller, Richard J.
, p. 2883 - 2887 (2007/10/02)
A new synthetic method is reported in which 2-arylbenzoxazoles can be prepared by palladium-catalyzed condensation of aryl halides with o-aminophenols followed by dehydrative cyclization.This method is tolerant of a wide variety of functional groups on either aromatic ring and gives good to excellent yields of products.An aliphatic vicinal amino alcohol gave a bis-acylated product as well as a chlorine-containing product with only a small amount of the desired 2-aryloxazole being formed.Methyl iodide and benzyl bromide gave only alkylated products.
