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Regiochemistry in 1,3-dipolar cycloadditions of the azomethine ylide formed from diethyl aminomalonate and paraformaldehyde
The azomethine ylide derived from the condensation of diethyl aminomalonate with paraformaldehyde undergoes 1,3-dipolar cycloadditions with acrylate and propiolate derivatives. Contrary to a previous report, these reactions yield mixtures of regioisomers
Blazey, Charles M.,Heathcock, Clayton H.
p. 298 - 300
(2002)
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Scalable synthesis of favipiravir: Via conventional and continuous flow chemistry
Decagram scale synthesis of favipiravir was performed in 9 steps using diethyl malonate as cheap starting material. Hydrogenation and bromination steps were achieved by employing a continuous flow reactor. The synthetic process provided a total of 16% yield and it is suitable for larger-scale synthesis and production. This journal is
Charoensetakul, Netnapa,Khamkhenshorngphanuch, Thitiphong,Srikun, Onsiri,Srimongkolpithak, Nitipol,Thongpanchang, Chawanee,Tiyasakulchai, Thanat,Yuthavong, Yongyuth
p. 38691 - 38693
(2021/12/20)

Preparation method of diethyl amino-malonate hydrochloride
The preparation method comprises first steps of preparing diethyl malonate in acetic acid, subnitration with an aqueous solution of nitrous acid to obtain the oxime-based malonic acid diethyl ester. 2nd: The oxime-based malonate is subjected to catalytic hydrogenation reaction with a nickel-containing ternary catalyst in an alcohol solvent to obtain diethyl amino-malonate. 3rd-Step: After the catalyst is filtered off, the catalyst is salified with hydrogen chloride ethanol and then dissolved in acetone to obtain diethyl amino-malonate hydrochloride. The method has the characteristics of mild and safe reaction conditions, simple and convenient operation, high yield, low cost, good quality and the like, and has wide application prospects. In addition, the hydrogenation technology for the method not only avoids waste residues and waste acid generated by reduction of zinc powder, but also avoids the disadvantages of expensive price and easy poisoning inactivation of the palladium-carbon catalyst.
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(2021/12/07)

A TRANSITION METAL COMPLEX COMPOUND
The present invention relates to a transition metal complex (Z) (described herein), which is stable and can be effectively used as a catalyst in various chemical transformations such as to prepare chemical intermediates, agrochemical compounds as well as pharmaceutical compounds.
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Page/Page column 17

(2021/07/31)

AN IMPROVED HYDROGENATION PROCESS USING A TRANSITION METAL COMPLEX CATALYST
The present invention relates to the process of reduction of compound of formula (II) by using a transition metal complex (Z) as a catalyst for hydrogenation reactions to get compound of formula (I). More particularly, the present invention relates to an improved process for the preparation of a compound (I) (as described herein) or a salt thereof; comprising hydrogenation of the compound (II) (as described herein) using a transition metal complex catalyst (Z).
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Page/Page column 28

(2021/07/31)

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition
An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.
Yu, Jhen-Kuei,Chien, Han-Wei,Lin, Yi-Jung,Karanam, Praneeth,Chen, Yu-Heng,Lin, Wenwei
supporting information
p. 9921 - 9924
(2018/09/11)

Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized ?-Aminobutyric Acid under Phosphine Catalysis
A phosphine-catalyzed reaction between o-hydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized ?-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem SN2′/2-aza-Cope rearrangement/intramolecular addition process.
Chen, Qingqing,Bao, Yishu,Yang, Xiuqin,Dai, Zonghao,Yang, Fulai,Zhou, Qingfa
supporting information
p. 5380 - 5383
(2018/09/13)

Organocatalytic Regiodivergent C?C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks
Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring-loaded” intermediate with switchable C?C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.
Cao, Jian,Fang, Ran,Liu, Jin-Yu,Lu, Hong,Luo, Yong-Chun,Xu, Peng-Fei
supporting information
p. 18863 - 18867
(2018/11/23)

Hydrogenolysis of geminal diazides
The complete hydrogenolysis of compounds containing the geminal diazido functionality is described. Using hydrogen over palladium on charcoal, the diazides are reduced, and primary amines are obtained. For example, aminomalonates and glycines are generated in a straightforward manner. A protocol that provides direct access to acetylated amines derived from 2-amino-1,3-diketones in good to excellent yields, via hydrogenation in the presence of acetic anhydride, is also presented.
Biallas, Phillip,Kirsch, Stefan F.
supporting information
p. 4209 - 4211
(2017/10/06)

An enantioselective cascade for simultaneous generation of five quaternary stereocenters from fully substituted enones
A highly enantioselective cascade reaction for the generation of five quaternary stereocenters in one-pot operation is reported for the first time in the history of organic synthesis. Cinchona-alkaloid derived hydrogen-bonding catalyst furnished structurally complex cascade products from simple substrates in excellent yields and stereoselectivities.
Yang, Shu-Mei,Reddy, Ganapuram Madhusudhan,Wang, Tzu-Ping,Yeh, Yu-Sheng,Wang, Min,Lin, Wenwei
supporting information
p. 7649 - 7652
(2017/07/12)

An efficient strategy for the synthesis of polysubstituted chromeno[4,3-b]pyrrolidine derivatives
A powerful cascade reaction was developed for the synthesis of chromeno[4,3-b]pyrrolidines with high yields and excellent stereoselectivities. This efficient cascade reaction expeditiously established two fused rings which bear three contiguous stereogenic centers including one quaternary stereocenter in a single operation with low catalyst loading under mild conditions.
Tian, Li,Xu, Guo-Qiang,Li, Yun-Han,Liang, Yong-Min,Xu, Peng-Fei
supporting information
p. 2428 - 2430
(2014/03/21)

Peroxisome proliferator-activated receptor-γ mediates the anti-inflammatory effect of 3-hydroxy-4-pyridinecarboxylic acid derivatives: Synthesis and biological evaluation
Seven 3-hydroxy-4-pyridinecarboxylic acid derivatives (HPs), aza-analogues of salicylic acid and structurally close to other potent inflammatory pyridine compounds such as aminopyridinylmethanols and aminopyridinamines, were synthesized, and their anti-inflammatory activity was evaluated. The synthesis was performed by adopting a general procedure involving an intramolecular Diels-Alder cycloaddition of oxazoles with acrylic acid to form various substituted pyridinic acids. The newly synthesized HPs did not exhibit cytotoxic activity on human monocytes-derived macrophages at concentrations up to 10 2 μM. Anti-inflammatory activity of the compounds was screened in vitro by evaluating the capability to inhibit cytokines release from lipopolysaccharide (LPS) stimulated human macrophages. 3-Hydroxy-1-methyl-4- pyridinecarboxylic acid (24) was found to be the most active HP. At 10 μM concentration, HP 24 reduced LPS-induced and nuclear factor-κB activation and cyclooxygenase-2 expression, while increased intracellular reactive oxygen species generation and peroxisome proliferator-activated receptor (PPAR-γ) mRNA transcript level. Indeed, pre-treatment of LPS-exposed human macrophages with PPAR-γ specific antagonist completely prevented HP 24-induced TNF-α and IL8 down regulation, demonstrating that the PPARγ pathway is mandatory for the HP 24 anti-inflammatory effect. Finally, daily treatment with HP 24 ameliorated the outcome of DSS-induced colitis in mice, significantly reducing colonic MPO activity and IL-1β tissue levels.
Brun, Paola,Dean, Annalisa,Di Marco, Valerio,Surajit, Pathak,Castagliuolo, Ignazio,Carta, Davide,Ferlin, Maria Grazia
p. 486 - 497
(2013/06/04)

SULFONIC ACID SALT COMPOUND OF 4-CARBAMOYL-5-HYDROXY-IMIDAZOLE DERIVATIVE
The object is to provide a stable SM-108 derivative, which is effective as a carcinostatic agent, particularly an SM-108 derivative having good storage stability. An SM-108 compound having good storage stability can be produced by producing an organic sulfonic acid salt compound of SM-108. Further, a crystalline SM-108 compound containing a trace amount of an organic carboxylic acid can be produced by using an aqueous solution of the organic sulfonic acid salt of SM-108, and by adding an alkali metal salt of an organic carboxylic acid to the aqueous solution to neutralize the aqueous solution and then causing the crystal precipitation in the solution.
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Page/Page column 6

(2010/07/03)

USE OF AMPK-ACTIVATING IMIDAZOLE DERIVATIVES, PREPARATION PROCESS THEREFOR AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
The invention relates to the use of imidazole derivatives of the formula (I): in which A, R'1, R'2 and R'3 are as defined in the description, as AMPK activators. The invention also relates to processes for the preparation of the said compounds, to their uses for the preparation of medicaments for the treatment of insulin resistance, diabetes and related pathologies, and also obesity, and to the pharmaceutical compositions comprising them. Certain compounds of the formula (I) are novel and, in this respect, also form part of the invention.
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Page/Page column 42

(2008/06/13)

NUCLEOSIDES WITH NON-NATURAL BASES AS ANTI-VIRAL AGENTS
A method and composition for treating a host infected with flavivirus, pestivirus or hepacivirus comprising administering an effective fiavivirus, pestivirus or hepacivirus treatment amount of a described base- modified nucleoside or a pharmaceutically acceptable salt or prodrug thereof, is provided.
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Page/Page column 129-130

(2008/06/13)

Syntheses of per-15N labeled etioporphyrins I-IV and a related tetrahydrobenzoporphyrin for applications in organic geochemistry and vibrational spectroscopy
Nitrogen-15 labeled pyrroles have been prepared from commercially available 15N glycine or sodium nitrite using the Barton-Zard, Knorr, and Kleinspehn approaches. These pyrroles were used as intermediates in the synthesis of per-15N labeled porphyrins needed for the analysis and assignment of vibrational spectra for sedimentary porphyrins. Etioporphyrin-I was prepared via pyrromethene intermediates, while etioporphyrins II-V and a related tetrahydrobenzoporphyrin were synthesized via stepwise routes involving the copper(II) mediated cyclization of a,c-biladienes as the key step. Detailed analyses of both the proton and carbon-13 NMR spectra provide nitrogen-15 coupling constants for these important structures.
Lash, Timothy D.,Chen, Shaohua
p. 11577 - 11600
(2007/10/03)

4-CARBONYL SUBSTITUTED 1,1,2-TRIMETHYL-1A,4,5,5A-TETRAHYDRO-1H-4-AZA-CYCLOPROPA'A!PENTALENE DERIVATIVES AS AGONISTS FOR THE G-PROTEIN-COUPLED RECEPTOR S1P1/EDG1 AND IMMUNOSUPPRESSIVE AGENTS
The invention relates to novel pyrrole compounds of the formula (I) wherein A represents -CH2CH2-, -CH=CH-, or -NH-CH2; Ar represents phenyl; mono-, di-, or tri-substituted phenyl, wherein the substituents are independently selected from halogen, lower alkyl, lower alkoxy, hydroxy-lower alkyl, hydroxy-lower alkoxy, 1-glyceryl, 2-glyceryl, cycloalkyl, mono- or di-lower alkylamino, methylenedioxy, ethylenedioxy, trifluoromethyl and trifluoromethoxy; or unsubstituted mono- or di-substituted 2-, 3- or 4-pyridyl, wherein the substituents are independently selected from lower alkoxy and hydroxy-lower alkoxy. The present invention provides novel compounds of formulae (I), (II) and (III) that are agonists for the G protein-coupled receptor S1P1/EDG1 and have a powerful and long-lasting immunosuppressive effect which is achieved by reducing the number of cirulating and infiltrating T- and B-lymphocytes, whitout affecting their maturation, memory or expansion. The reduction of circulating T-/B-lymphocytes as a result of S1P1/EDG1 agonism, possibly in combination with the observed improvement of endothelial cell layer function associated with S1P1/EDG1 activation, makes such compounds useful to treat uncontrolled inflammatory disease and to improve vascular functionality.
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Page/Page column 18-19

(2010/02/15)

Improved Reagent for Electrophilic Amination of Stabilized Carbanions
(Equation presented) Enolate amination using O-di(p-methoxyphenyl) phosphinylhydroxylamine 2 is reported. Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78°C.
Smulik, Jason A.,Vedejs, Edwin
p. 4187 - 4190
(2007/10/03)

Reactivity of 3-ethoxycarbonyl isoquinolinium salts towards various nucleophilic reagents: Applications to the synthesis of new 1,2- dihydroisoquinoline-3-carboxylates
Different types of novel 1,2-disubstituted 1,2-dihydro isoquinolines were synthesized by addition reactions of organolithium, alcoholates and borohydride reagents with various isoquinolinium salts. The leaving group character of the isoquinoline moiety was also evidenced.
Meziane, Mohamed Ameziane Ait Amer,Bazureau, Jean Pierre
p. 252 - 263
(2007/10/03)

Ring-expanded nucleosides and nucleotides
The present invention relates to compositions comprising analogues of purine nucleotides containing a ring-expanded ("fat") heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS) and hepatitis.
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Example 6

(2008/06/13)

Indole derivatives
The novel indole derivatives and salts thereof represented by the general formula (1) STR1 possess, for example, an inhibitory effect against superoxide (O2-) released from the macrophage cells of guinea pig by stimulation and an anti-albuminuria activity against Masugi nephritis, and are useful in various clinical fields as an agent for preventing and treating diseases and cases associated with the above superoxide radical, for example, autoimmune diseases (e.g. rheumatism), arteriosclerosis, ischemic disease, ischemic encephalopathia, hepatic insufficiency and renal insufficiency, and also as an agent for preventing and treating nephritis.
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(2008/06/13)

Porphyrins with Exocyclic Rings. 2. Synthesis of Geochemically Significant Tetrahydrobenzoporphyrins from 4,5,6,7-Tetrahydro-2H-isoindoles
Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum.Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins.Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described.Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone.Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield.Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and /or 37b gave a series of a,c-biladiene dihydrobromides.Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15percent sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield.This work provides a general route for the synthesis of these important porphyrin molecular fossils.
May, Donald A.,Lash, Timothy D.
p. 4820 - 4828
(2007/10/02)

Stereoisomeric tricyclic bis(dioxopiperazines) and pharmaceutical compositions
Stereoisomeric tricyclic bis(dioxopiperazines) of the formula STR1 wherein R is H or STR2 and the processes for the synthesis thereof are provided. The compounds are effective as antitumor or antimetastatic drugs.
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(2008/06/13)

Regioselectivity of Pyrrole Synthesis fromm Diethyl Aminomalonate and 1,3-Diketones: Further Observations
1,3-Diketones 1 react with diethyl aminomalonate (2) in boiling acetic acid to afford ethyl 2-pyrrolecarboxylates 6.Considerable regioselectivity was noted for the following classes of diketone: 2-acylcyclohexanones 10a,b , 2-acylcyclopentanones 10c,d pyrroles 13a,b>, 1-phenyl-2-alkyl-1,3-alkanediones 17a-d , 3-phenyl-2,4-hexanedione (21a) , 1-phenyl-3-alkyl-2,4-alkanediones 24a,b , and 2,2-dimethyl-3,5-alkanediones 29a,b .The yields varied with the structural class, decreasing with increased steric hindrance.The product structure correlated with the structure of the enolized diketones in the case of the 2-acylcycloalkanones studied.
Paine, John B.,Brough, Jonathan R.,Buller, Kathy K.,Erikson, Erika E.
p. 3986 - 3993
(2007/10/02)

A Facile Synthesis of α-Amino Esters via Reduction of α-Nitro Esters Using Ammonium Formate as a Catalytic Hydrogen Transfer Agent
Various nitroesters 3 were selectively and rapidly reduced to their corresponding amino esters 4 in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent.
Ram, Siya,Ehrenkaufer, Richard E.
p. 133 - 135
(2007/10/02)

DERIVATIVES OF IMINOMALONIC ESTER
The synthesis of (alkylimino)malonic esters was realized by the reaction of alkylamines with mesoxalic or dibromomalonic ester. (Halogenimino)malonic esters were obtained for the first time by the reaction of aminomalonic ester with tert-butyl hypochlorite or sodium hypobromite.A new method was developed for the synthesis of (acylimino)malonic esters by the successive bromination and dehydrobromination of (acylamino)malonic esters.The addition of various nucleophiles (water, amines, formamide) at the C=N bond of (acylimino)malonic esters was studied.
Prosyanik, A. V.,Fedoseenko, D. V.,Markov, V. I.
p. 1494 - 1503
(2007/10/02)

Pyrrole Chemistry. An Improved Synthesis of Ethyl Pyrrole-2-carboxylate Esters from Diethyl Aminomalonate
Ethyl pyrrole-2-carboxylates, versatile precursors for the total synthesis of both synthetic model and naturally occurring tetrapyrroles and porphyrins, can be prepared in greatly improved yields by the addition of 1,3-diketones and preformed diethyl aminomalonate to boiling glacial acetic acid.The method is suitable for both small- and large-scale synthesis and has proved far more reliable than the original in situ dissolving zinc reduction of diethyl oximinomalonate discovered by Kleinspehn.Yields range from 60-70percent for the dominant product isomer from unsymmetrical diketones to 75-90percent for the single product derived from symmetrical diketones.Seventeen examples of alkyl-substituted ethyl pyrrole-2-carboxylates are provided.Improved procedures are given for the preparation of the required precursors.
Paine, John B.,Dolphin, David
p. 5598 - 5604
(2007/10/02)

The Synthesis and Chemistry of Azolenines. Part 4. Preparation and Rearrangement of some 3,5-Diaryl-2H-pyrrole-2,2-dicarboxylic Esters
Oxidation of diethyl 3,5-diaryl-3,4-dihydro-2H-pyrrole-2,2-dicarboxylates (3) with chloranil in refluxing xylene gives not the 3,5-diaryl-2H-pyrrole-2,2-dicarboxylates (4) as reported by an earlier group, but instead the rearranged, isomeric, 1H-pyrrole-1,2-dicarboxylates (5). 2H-Pyrroles (4) may be obtained from the dihydropyrroles (3) using DDQ in benzene at room temperature; they rearrange to the isomers (5) in boiling xylene via an acyl -sigmatropic shift from carbon to nitrogen, a novel process in the 2H-pyrrole series.Thermal analyses indicate that the rearrangement is concerted with negligible charge separation in the transition state.Other novel 3,5-diaryl-1H-pyrrole-2-carboxylic acid derivatives are described.
Sammes, Michael P.,Chung, Margaret W. L.,Katritzky, Alan R.
p. 1773 - 1780
(2007/10/02)

The Synthesis and Application of Novel Nitrating And Nitrosating Agents
Alcohols and phenols are efficiently nitrated with thionyl chloride nitrate or thionyl nitrate, even in the presence of an aromatic moiety.While thionyl chloride nitrate is suitable for nitration of primary OH-groups in carbohydrates, thionyl nitrate is reactive enough to react with secondary OH-groups as well.These reagents permit the highly selective nitration of the 5'-, 2',5'- and 3',5'-OH-groups of ribonucleosides to produce either mono- or diprotected nitro derivatives in high yields.Carbon acids and the enol form of some ketones are efficiently nitrated with trifluoromethanesulfonyl nitrate/potassium tert-butoxide.Lutidine N-oxide(2,6-(CH3)2C5H3N->O) was found to have marked effect on nitration reactions.Similarly, thionyl chloride nitrite and thionyl nitrite exhibit an excellent capacity for nitrosation of the aforementioned substrates
Hakimelahi, Gholam H.,Sharghi, Hashem,Zarrinmayeh, Hamide,Khalafi-Nezhad, Ali
p. 906 - 915
(2007/10/02)