19347-73-0Relevant articles and documents
On the reactions between phosphorus pentachloride and lactones
Ismaili, Valeh Mehralioglu,Aydin, Adnan,Kantaeva
, p. 137 - 142 (1999)
Reactions between PCl5 and substituted or unsubstituted β-, γ- and ε-lactones have been investigated. Although γ-butyrolactone substituted at α-position with an alkyl radical has given phosphorylated products of both cyclic ethers and chlorinated carboxylic acid chlorides along with γ-chlorobutanoic acid chloride, halogen substituted γ-butyrolactone such as α-bromo-γ-butyrolactone yielded α-bromo-γ-chlorobutanoic acid chloride in similar manner with β-propiolactone which gives β-chloropropionic acid chloride. The nature of radicals present at γ-position also affects the reaction products. Methyl or heptyl radicals yielded different products; in the latter case phosphorylated products were not isolated. The reaction pathway of ε-caprolactone with PCl5 is changed by the temperature of the reaction mixture. It reacts at 20-30°C to give α,α-dichlorooxepane and ε-chlorohexanoic acid chloride, while a phosphorylated product was observed at 60-70°C. Possible mechanisms of these reactions are discussed.
An investigation of the synthesis of vilazodone
Hu, Fan,Su, Weike
, p. 243 - 247 (2020/01/08)
A novel synthetic route toward vilazodone is described by using 4-cyanoaniline and 5-bromo-2-hydroxybenzaldehyde as starting materials, with an overall yield of 24% and 99% purity. First, the intermediate (3-(4-chlorobutyl)-1H-indole-5-carbonitrile) is synthesized via diazotization of 4-cyanoaniline, followed by Fischer indole cyclization with 6-chlorohexanal. Subsequently, another intermediate, 5-(piperazin-1-yl)benzofuran-2-carboxamide, is generated via aromatic nucleophilic substitution of 5-bromobenzofuran-2-carboxamide with piperazine. Finally, vilazodone is obtained via nucleophilic substitution of the above two key intermediates by treatment with Et3N/K2CO3. In comparison to the original process, this route avoids the use of expensive and toxic reagents and resolves issues such as safety, environmental concerns, and high costs.
Catalytic asymmetric reductive acyl cross-coupling: Synthesis of enantioenriched acyclic α,α-disubstituted ketones
Cherney, Alan H.,Kadunce, Nathaniel T.,Reisman, Sarah E.
supporting information, p. 7442 - 7445 (2013/06/27)
The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a NiII/bis(oxazoline) catalyst in the presence of Mn0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.
Polyamine biosynthesis inhibitors
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, (2008/06/13)
A compound having the formula: STR1 wherein R is STR2 wherein R' is hydrogen or aminopropyl and salts thereof.
Free Radical Substitution. Part 37. The Effect of Solvent on the Atomic Chlorination of 1-Substituted Butanes and Related Compounds
Potter, Alan,Tedder, John M.
, p. 1689 - 1692 (2007/10/02)
Experimental results reported in this paper show that the relative selectivity of atomic chlorination of 1-substituted butanes and related compounds is greatly influenced by the phase and by solvents.Solvents can be divided into three classes: (a) inert, (b) solvents which decrease the selectivity, and (c) solvents which increase the selectivity.The second group solvate the transition state and the third group solvate the chlorine atoms.
