15898-67-6Relevant academic research and scientific papers
In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)
Hoye, Thomas R.,Kopel, Lucas C.,Ryba, Troy D.
, p. 1572 - 1574 (2006)
A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-p
FERROPORTIN INHIBITORS AND METHODS OF USE
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Paragraph 0738; 0739, (2020/07/07)
The subject matter described herein is directed to Ferroportin inhibitor compounds of Formula I and pharmaceutical salts thereof, methods of preparing the compounds, pharmaceutical compositions comprising the compounds and methods of administering the compounds for prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, particularly iron overload states, such as thalassemia, sickle cell disease and hemochromatosis.
A highly nucleophilic multifunctional chiral phosphane-catalyzed asymmetric intramolecular rauhut-currier reaction
Zhang, Xiao-Nan,Shi, Min
supporting information, p. 6271 - 6279 (2013/01/15)
An asymmetric variant of the intramolecular Rauhut-Currier (RC) reaction can be achieved using a highly nucleophilic multifunctional chiral phosphane; the corresponding cyclopentene and cyclohexene derivatives are produced in moderate to good yields and w
Iron-mediated and -catalyzed metalative cyclization of electron- withdrawing-group-substituted alkynes and alkenes with grignard reagents
Hata, Takeshi,Sujaku, Shiro,Hirone, Naoki,Nakano, Kirihiro,Imoto, Junsuke,Imade, Haduki,Urabe, Hirokazu
supporting information; scheme or table, p. 14593 - 14602 (2012/02/04)
Treatment of ethyl (E)-5,5-bis[(benzyloxy)methyl]-8-(N,N-diethylcarbamoyl)- 2-octen-7-ynoate with an iron reagent generated from FeCl2 and tBuMgCl in a ratio of 1:4 (abbreviated as FeCl2/4 tBuMgCl) afforded ethyl [4,4-bis[(benzyloxy)methyl]-2-[(E)-(N,N-diethylcarbamoyl)methylene] cyclopent-1-yl]acetate in good yield. Deuteriolysis of an identical reaction mixture afforded the bis-deuterated product ethyl [4,4-bis[(benzyloxy)methyl]-2- [(E)-(N,N-diethylcarbamoyl)deuteriomethylene]cyclopent-1-yl]deuterioacetate, thus confirming the existence of the corresponding dimetalated intermediate. The latter intermediate can react with halogens or aldehydes to facilitate further synthetic transformations. The amount of FeCl2 was reduced to catalytic levels (10 mol% relative to enyne), and catalytic cyclizations of this sort proceeded with yields comparable to those of the aforementioned stoichiometric reactions. The cyclization of diethyl (E,E)-2,7-nonadienedioate with a stoichiometric amount of FeCl2/4 tBuMgCl, followed by the addition of sBuOH as a proton source, afforded a mixture of 2-(ethoxycarbonyl)- 3-bicyclo[3.3.0]octanone and its enol form in good yield. The use of aldehyde or ketone in place of sBuOH afforded 2-(ethoxycarbonyl)-3-bicyclo[3.3.0]octanone, which has an additional hydroxyalkyl side chain. Additionally, the metalation of a carbon-carbon unsaturated bond in N,N-diethyl-5,5-bis[(benzyloxy)methyl]-7,8- epoxy-2-octynamide or (E)-3,3-dimethyl-6-(N,N-diethylcarbamoyl)-5-hexenyl p-toluenesulfonate with FeCl2/4 tBuMgCl or FeCl2/4 PhMgBr was followed by an intramolecular alkylation with an epoxide or alkyl p-toluenesulfonate to afford 5,5-bis[(benzyloxy)methyl]-3-[(E)-(N,N- diethylcarbamoyl)methylene]-1-cyclohexanol or N,N-diethyl(3,3- dimethylcyclopentyl)acetamide after hydrolysis. In both cases, the remaining metalated portion α to the amide group was confirmed by deuteriolysis and could be utilized for an alkylation with methyl iodide.
Effect of phase transfer chemistry, segmented fluid flow, and sonication on the synthesis of cinnamic esters
Riccaboni, Mauro,La Porta, Elena,Martorana, Andrea,Attanasio, Roberta
experimental part, p. 4032 - 4039 (2010/07/06)
Wittig reaction under Phase Transfer conditions was performed in a flow reaction system. Different bases, aldehydes, phosphonium salts, and flow reaction parameters were investigated, in absence of a phase transfert catalyst. An improvement of the reaction outcome (yield and reaction time) was achieved through the immersion of the reactor into an ultrasound bath.
In situ generation of ylides for tandem oxidation-olefination reactions of unactivated diols
Phillips, David J.,Graham, Andrew E.
, p. 649 - 652 (2008/12/20)
An efficient desymmetrization of diols is achieved using phosphonium salts which undergo deprotonation in the presence of a hindered amine base and manganese dioxide to produce α,β-unsaturated hydroxy esters in good yields. Georg Thieme Verlag Stuttgart.
Iron-mediated intramolecular metalative cyclization of α,β- unsaturated esters and amides. Versatile one-pot preparation of bicyclic ketoesters
Hata, Takeshi,Hirone, Naoki,Sujaku, Shiro,Nakano, Kirihiro,Urabe, Hirokazu
supporting information; experimental part, p. 5031 - 5033 (2009/05/31)
(Chemical Equation Presented) 2-Nonen-7-ynedioic or 2-decen-8-ynedioic acid derivatives were treated with an iron reagent generated from FeCl2 and t-BuMgCl in a ratio of 1:4 to give cyclized products after hydrolysis, deuteriolysis, or the addition of carbonyl compounds. Upon reaction with the same iron reagent, 2,7-nonadienedioates afforded bicyclic ketoesters (and their enol forms) after the addition of s-BuOH or carbonyl compounds.
A PROCESS FOR PREPARING DIAZABICYCLO[3.3.1] NONANE COMPOUNDS
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Page/Page column 47, (2008/12/07)
The invention is a process for preparing a diazabicyclo compound of formula (I) process for preparing a diazabicyclo compound of formula (I):where X is selected from the group consisting of hydrogen, C1-C6 alkoxycarbonyl, and carbobenzyloxy; R6 is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, and benzyl; and R9, R 10, and R11 are independently selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl. wherein the process involves cyclizing I-I, formula (II).
Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters
Phillips, David J.,Pillinger, Kathryn S.,Li, Wei,Taylor, Angela E.,Graham, Andrew E.
, p. 10528 - 10533 (2008/02/13)
The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical or unsymmetrical dienyl diesters using a second oxidation/Wittig olefination sequence mediated by PCC.
Facile synthesis of α,α′ disubstituted N-hydroxypyrrolidines and N-hydroxypiperidines via double 1,4-addition of hydroxylamine
Bargiggia, Frédéric C.,Murray, William V.
, p. 3191 - 3193 (2007/10/03)
A versatile synthesis of α and α′ disubstituted N-hydroxypiperidine and N-hydroxypyrrolidine by consecutive double 1,4-addition of hydroxylamine on the corresponding bis α,β-unsaturated diester is described. This reaction takes place an environmentally friendly (ethanol/water) system and at room temperature.
