22042-72-4Relevant academic research and scientific papers
Preparation method of silodosin intermediate
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Paragraph 0043-0046; 0053-0056; 0063-0066; 0073-0076, (2019/04/13)
The invention discloses a preparation method of a silodosin intermediate and relates to the technical field of chemical synthesis of drugs. The preparation method comprises the following steps: subjecting salicyaldehyde and ethylene carbonate to transesterification to obtain 2-(2-hydroxyethoxy)benzaldehyde; then, carrying out a Dakin oxidation reaction to obtain sodium 2-(2-hydroxyethoxy) phenol;then, subjecting sodium 2-(2-hydroxyethoxy) phenol and trifluoroethanol to an etherification reaction to obtain 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl alcohol; and finally, subjecting 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl alcohol and methanesulfonyl chloride to an esterfication reaction to obtain the silodosin intermediate 2-[2-(2,2,2-trifluoroethyoxy)phenoxy]ethyl methanesulfonate. The preparation method is novel and short in synthesis route, and a target product can be prepared by only four-step reaction. Both raw materials and reagents used for preparation are cheap, available andenvironment-friendly, all the reaction conditions are mild and controllable, the preparation method is convenient and simple in operation, and the prepared silodosin intermediate is high in purity andyield, suitable for industrial production and wide in prospect and industrial application value.
Efficient catalytic, oxidative lactonization for the synthesis of benzodioxepinones using thiazolium-derived carbene catalysts
Rose, Christopher A.,Zeitler, Kirsten
supporting information; experimental part, p. 4552 - 4555 (2010/12/25)
An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions. The react
N-heterocyclic carbene catalyzed nucleophilic substitution reaction for construction of benzopyrones and benzofuranones
He, Jinmei,Zheng, Jiyue,Liu, Jian,She, Xuegong,Pan, Xinfu
, p. 4637 - 4640 (2007/10/03)
N-Heterocyclic carbene as an efficient organic catalyst was employed to catalyze an intramolecular nucleophilic substitution reaction. When R 2 was a phenyl group, the cyclization process underwent isomerization, leading to generation of benzofuranone.
Ortho-directed lithiation of ω-phenoxy alcohols
Salteris, Constantinos S.,Kostas, Ioannis D.,Micha-Screttas, Maria,Heropoulos, George A.,Screttas, Constantinos G.,Terzis, Aris
, p. 5589 - 5592 (2007/10/03)
ω-Phenoxy alcohols, PhO(CH2)(n)OH (n = 2-7), have been subjected to metalation with 2 equiv of n-butyllithium in tetrahydrofuran/methylcyclohexane solvent. Reaction of the resulting lithiated compounds with carbon dioxide (n = 2-7), benzaldehyde (n = 2-6), benzophenone (n = 2, 3), dimethylformamide (n = 2), ethyl formate (n = 2), and chlorodiphenylphosphine (n = 3) afforded the corresponding ortho- substituted hydroxyalkoxybenzenes in yields ranging from 45 to 83%. The synthesis is also reported of five new bis[o-(ω-hydroxyalkoxy)phenyl]mercury compounds (n = 2-6), four crystal structures of which have been determined.
1,4-dihydropyridine derivatives
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, (2008/06/13)
Compounds a formula (I) STR1 wherein the substituents and symbols have the meanings given in the specification, are new compounds with marked cardiovascular activity.
The Role of Substituents and Solvents in Promoting "Medium-Size" Ring-Chain Tautomerism
Jones, Paul R.,Jaglowski, Adam J.
, p. 3891 - 3896 (2007/10/02)
Two series of o-hydroxyalkoxybenzaldehydes have been examined by 1H and 13C NMR for their tendency to exhibit ring-chain tautomerism.All members of the diethylenoxy family exist as chain tautomers rather than partially or wholly as the 10-membered rings.The ethylenoxy compounds in solution are mixtures of chain and 7-membered ring tautomers in every case where a substituent is present on the aromatic ring ortho to the alkoxy group.Ring-chain equilibrium constants, determined by 1H NMR integration of methine and formyl peaks, varied as much as 100-fold with substituents and solvent.A good correlation is noted between percent ring tautomer and the size of the ortho substituent.A second substituent para to the alkoxy group enhances K considerably, even though K = 0 in cases where there is only a para substituent.
Intramolecular Cycloadditions with Carbonyl Ylides: From Oxiranes to Large Ring Systems
Brokatzky-Geiger, Juergen,Eberbach, Wolfgang
, p. 2157 - 2192 (2007/10/02)
Within the classes of 1,3-dipoles intramolecular cycloaddition reactions with carbonyl ylides, accessible by heating of the oxirane precursors 4-10, are studied for the first time in a systematic manner.Although the formation of the corresponding fused and/or bridged tetrahydrofuran derivatives (32-34, 44-46, 50-63) has been established in all cases with the exception of 4e and 6a, the rate of formation as well as the yield of the cycloadducts depend strongly on the dipolarophilicity of the olefinic component: Whereas non-activated C=C bonds undergo the cycloaddition step slowly and only when being arranged in a relatively close position to the dipole unit (the maximum size of the second ring, formed by "tieing": 9-membered), ene-oxiranes with an electron deficient double bond are reacting much faster and (in contrast to cycloadditions so far known for other 1,3-dipoles) also at a large distance between the ?-centers.In this way macrocycles with up to 34 ring members have been obtained.This high regio- and stereoselectivity observed in most cases of the cycloadditions is explained mainly by steric factors.
