17190-25-9Relevant academic research and scientific papers
Novel process for the synthesis of class I antiarrhythmic agent (±)-cibenzoline and its analogs
Gholap, Atul R.,Paul, Vincent,Srinivasan, Kumar V.
, p. 2967 - 2982 (2008/12/22)
Synthesis of (±)-cibenzoline and its analogs has been achieved by a simple sequence of reactions. The diaryl cyanoolefin intermediate 3 could be prepared by Knoevenagel condensation of benzophenone with ethylcyanoacetate to form the tetra-substituted olefin intermediate 2 followed by Krapcho deethoxycarbonylation or from β-hydroxynitrile intermediate 2' followed by the elimination of hydroxyl group respectively. The 2,2- diphenylcyclopropanecarbonitrile 4 was synthesized from intermediate 3 by cyclopropanation, which was converted to (±)-2-(2,2-diphenylcyclopropyl)- 2-imidazoline 5 by reaction with ethylenediamine in the presence of a catalytic amount of sulfur. Moreover, the obtained 2-imidazolines were smoothly oxidized to the corresponding imidazoles 6 in good to moderate yields. Copyright Taylor & Francis Group, LLC.
Cerium (III) chloride mediated nitrile aldol reactions: Enhanced diastereoselectivities using a chiral organocerium complex
Xiao, Zejun,Timberlake, Jack W.
, p. 4211 - 4222 (2007/10/03)
The addition of anhydrous cerium chloride to nitrile aldol reactions has been found to provide high yields of [β-hydroxynitriles. Also, the aldol reaction of α, β-unsaturated carbonyl compounds with nitrile enolates in the presence of cerium chloride affo
Substituted 1,2,3,4-Tetrahydroaminonaphthols: Antihypertensive Agents, Calcium Channel Blockers, and Adrenergic Receptor Blockers with Catecholamine-Depleting Effects
Atwal, Karnail S.,O'Reilly, Brian C.,Ruby, Eric P.,Turk, Chester F.,Aberg, Gunnar,et al.
, p. 627 - 635 (2007/10/02)
Substituted 1,2,3,4-tetrahydroaminonaphthols were found to be calcium channel blockers with antihypertensive properties.These compounds also possessed adrenergic β-receptor blocking activity.From the structure-activity studies, no clear correlation emerged between the in vitro calcium channel blocking activity and the acute antihypertensive activity in cannulated spontaneously hypertensive rats.Extensive pharmacological testing of selected compounds indicated that aminonaphthols are antihypertensive agents with many pharmacological properties.The relative contribution of various pharmacological actions toward the observed antihypertensive activity is unclear.Since the clinically useful calcium channel blocker verapamil is structurally related to these compounds, one of the aminonaphthols, trans-3--1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphthalenol (12), was compared with verapamil for calcium channel blocking activity, adrenergic blocking activity, and catecholamine-depleting activity.Both compopunds were found to be equipotent in these test systems.
Reaction entre solvant et especes intermediaires apparues lors de l'electroreduction-acylation de la fluorenone et de la fluorenone-anil dans l'acetonitrile
Degrand, Chantal,Belot, Gerard,Compagnon, Paul-Louis,Gasquez, Francoise
, p. 2581 - 2589 (2007/10/02)
The electrogenerated anions CH2CN- induce the conversion of the various reduction-acylation products of fluorenone 1a and its anil 1b in acetonitrile into 1a and 1b; this phenomenon is controlled by the fortuitous introduction of molecular oxygen.The CH2CN- anions catalyse the transformation of 1a and 1b into fluorenylideneacetonitrile (FlC=CHCN) 17, convertible into the nitriles FlC=CH(CN)=C(NH2)CH3 8, FlC=C(CN)CHFl 10, and FlC(CN)CH2CN 11.These observations allow us to interpret the formation of the products appearing during the electrolysis of fluorenone in acetonitrile in the presence of an equivalent of chloride or anhydride of ω-chloro acid.The products of reduction-acylation appear successively, followed by the nitriles, FlC(OH)CH2CH2CN 3a, 10, FlC(OH)CH2CN 24, and polymers.Because of its basicity the fluorenone radical anion promotes reactions with the solvent, olefin 17 being a preferred intermediate.Bis-fluorenol, fluorenol, and finally fluorene and found with 1a and the above products.
