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Dicarbonyls 1,3-compounds

The synthesis of pyrazolcs starting from a hydrazine and a 1,3-dicarbonyl compound is a well established reaction in organic synthesis. If a mono-suhstituted hydrazine is reacted with an unsymmctrically substituted 1,3-dicarbonyl compound, two different pyrazole products which arc regioisomers could he formed (sec figure 10.3-2). [Pg.545]

You see that this reaction makes a 1,5-dicarbonyl compound we can therefore disconnect any such compound at either of the two middle bonds. [Pg.36]

We now have a 1,5-dicarbonyl compound with one good disconnection ... [Pg.37]

Since cyclohexenes can also be made by the Diels-Alder reaction (frames 5-8) we have access to a wide range of 1,6-dicarbonyl compounds. How about TM 196 ... [Pg.60]

Analysis First convert the 1,6-dioxygenated compound to a 1,6-dicarbonyl compound, keeping the two carbonyl groups different ... [Pg.61]

Discoimection of other combinations of functional groups can lead us back to a 1,6-dicarbonyl compound. Try this on TM 201. [Pg.62]

Analysis This is a 1,5-dioxygenated skeleton, therefore further FGl is necessary to give a 1,5-dicarbonyl compound. [Pg.63]

Analysis Our methods for making 1,2-dioxygenated compounds (frames 154-157) involve reductive linking of a dicarbonyl compound ... [Pg.95]

This is a 1,6-dicarbonyl compound so we must re-connect into a cyclohexene. [Pg.98]

Both A and B are 1,5-dicarbonyl compounds, but only B can be discormected in the usual way. The result is two molecules of an a,p-unsaturated ketone and we can continue the analysis ... [Pg.109]

Analysis This is a 1,6-dicarbonyl compound so a recormection is called for. The next obvious series (frames 36-8) of discormections ends up at 382B - not an easy compound to make. Where could we put a carbonyl group in 382A to allow some more helpfiil discormections ... [Pg.121]

Analysis Taking the heterocychc part first, we can remove the two heteroatoms as hydroxylamine (the approach of frames 258-261) to give us a 1,3-dicarbonyl compound. [Pg.130]

Analysis Another lactone FGl reveals the true TM (A). Our normal discormection a of an a,p-unsaturated carbonyl compound gives us the 1,5-dicarbonyl compound (B) and the ketone (C) clearly derived from phenol. Alternatively we could disconnect bond b to the keto-ester (D) with the further discormection shown ... [Pg.131]

The most general methods for the syntheses of 1,2-difunctional molecules are based on the oxidation of carbon-carbon multiple bonds (p. 117) and the opening of oxiranes by hetero atoms (p. 123fl.). There exist, however, also a few useful reactions in which an a - and a d -synthon or two r -synthons are combined. The classical polar reaction is the addition of cyanide anion to carbonyl groups, which leads to a-hydroxynitriles (cyanohydrins). It is used, for example, in Strecker s synthesis of amino acids and in the homologization of monosaccharides. The ff-hydroxy group of a nitrile can be easily substituted by various nucleophiles, the nitrile can be solvolyzed or reduced. Therefore a large variety of terminal difunctional molecules with one additional carbon atom can be made. Equally versatile are a-methylsulfinyl ketones (H.G. Hauthal, 1971 T. Durst, 1979 O. DeLucchi, 1991), which are available from acid chlorides or esters and the dimsyl anion. Carbanions of these compounds can also be used for the synthesis of 1,4-dicarbonyl compounds (p. 65f.). [Pg.50]

Treatment of O-silyl enols with silver oxide leads to radical coupling via silver enolates. If the carbon atom bears no substituents, two such r -synthons recombine to symmetrical 1,4-dicarbonyl compounds in good vield (Y. Ito, 1975). [Pg.65]

Cyclohexene derivatives can be oxidatively cleaved under mild conditions to give 1,6-dicarbonyl compounds. The synthetic importance of the Diels-Alder reaction described above originates to some extent from this fact, and therefore this oxidation reaction is discussed in this part of the book. [Pg.87]

Conventional synthetic schemes to produce 1,6-disubstituted products, e.g. reaction of a - with d -synthons, are largely unsuccessful. An exception is the following reaction, which provides a useful alternative when Michael type additions fail, e. g., at angular or other tertiary carbon atoms. In such cases the addition of allylsilanes catalyzed by titanium tetrachloride, the Sakurai reaction, is most appropriate (A. Hosomi, 1977). Isomerization of the double bond with bis(benzonitrile-N)dichloropalladium gives the y-double bond in excellent yield. Subsequent ozonolysis provides a pathway to 1,4-dicarbonyl compounds. Thus 1,6-, 1,5- and 1,4-difunctional compounds are accessible by this reaction. [Pg.90]

Pyrroles from 1,4-dicarbonyl compounds and ammonia isoxazolines from olefins and nitrile oxides. [Pg.96]

Several 1,4-dicarbonyl compounds are prepared based on this oxidation. Typically, the 1,4-diketone 10 or the 1,4-keto aldehyde 12 can be prepared by the allylation of a ketone[24] or aldehyde[61,62], followed by oxidation. The reaction is a good annulation method for cyclopentenones (11 and 13). Syntheses of pentalenene[78], laurenene[67], descarboxyquadrone[79], muscone (14 R = Me)[80]) and the coriolin intermediate 15[71] have been carried out by using allyl group as the masked methyl ketone (facing page). [Pg.24]

Butyl vinyl ether reacts with aroyl chlorides using Pd(OAc)2 without a ligand to give the unsaturated ketone 839, which is a precursor of a 1-aryl-1,3-dicarbonyl compound. The reaction is regioselective /3-attack. Addition of PhjP inhibits the reaction[718]. [Pg.253]

This reaction was first described by Gabriel in 1910 (40), when he warmed an acylaminoketone (197a) with an equimolecular amount of phosphorus pentasulfide. The reaction (Scheme 103) is similar to the preparation of other five-membered oxygen- and sulfur-containing rings from 1,4-dicarbonyl compounds. [Pg.278]

Cyclic diols give dicarbonyl compounds The reactions are faster when the hydroxyl groups are cis than when they are trans but both stereoisomers are oxidized by periodic acid... [Pg.648]

The two most important structural features that stabilize the enol of a (3 dicarbonyl compound are... [Pg.762]

Enolate ions of p dicarbonyl compounds are useful intermediates m organic synthesis We shall see some examples of how they are employed m this way later m the chapter... [Pg.765]

Aldol condensations of dicarbonyl compounds—even diketones—occur mtramo lecularly when five or six membered rings are possible... [Pg.773]

Most of the reactions of ester enolates described so far have centered on stabilized eno lates derived from 1 3 dicarbonyl compounds such as diethyl malonate and ethyl ace toacetate Although the synthetic value of these and related stabilized enolates is clear chemists have long been interested m extending the usefulness of nonstabilized enolates derived from simple esters Consider the deprotonation of an ester as represented by the acid—base reaction... [Pg.902]

Vinyl ethers and a,P unsaturated carbonyl compounds cyclize in a hetero-Diels-Alder reaction when heated together in an autoclave with small amounts of hydroquinone added to inhibit polymerisation. Acrolein gives 3,4-dihydro-2-methoxy-2JT-pyran (234,235), which can easily be hydrolysed to glutaraldehyde (236) or hydrogenated to 1,5-pentanediol (237). With 2-meth5lene-l,3-dicarbonyl compounds the reaction is nearly quantitative (238). [Pg.115]

In addition to formation from a ketone, the hydra2ones can be obtained from dicarbonyl compounds by a Japp-Klingemann reaction. This is especially useful for P-ketoesters and P-ketoacids, which undergo either deacylation or decarboxylation. [Pg.86]

Insertion Reactions. Isocyanates also may undergo iasertion reactions with C—H bonds. Acidic compounds, such as 1,3-dicarbonyl compounds (6), react readily at room temperature to form carboxyamides. At higher temperatures carboxyamides frequentiy undergo secondary reactions leading to cyclized products (33,34). [Pg.449]

Carbon—nitrogen double bonds in imines, hydrazones, oximes, nitrones, azines, and substituted diazomethanes can be cleaved, yielding mainly ketones, aldehydes and/or carboxyHc acids. Ozonation of acetylene gives primarily glyoxal. With substituted compounds, carboxyHc acids and dicarbonyl compounds are obtained for instance, stearoHc acid yields mainly azelaic acid, and a smaH amount of 9,10-diketostearic acid. [Pg.493]


See other pages where Dicarbonyls 1,3-compounds is mentioned: [Pg.90]    [Pg.30]    [Pg.35]    [Pg.54]    [Pg.60]    [Pg.11]    [Pg.65]    [Pg.79]    [Pg.151]    [Pg.248]    [Pg.187]    [Pg.762]    [Pg.765]    [Pg.1012]    [Pg.477]    [Pg.254]    [Pg.42]    [Pg.44]    [Pg.45]   


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1 ,3- Dicarbonyl compounds Michael addition with

1 ,3- Dicarbonyl compounds cleavage

1 ,3- Dicarbonyl compounds synthesis

1,3-Dicarbonyl compounds acidity

1,3-Dicarbonyl compounds asymmetric Michael addition

1,3-Dicarbonyl compounds cascades

1,3-Dicarbonyl compounds chiral metal complexes

1,3-Dicarbonyl compounds enantioselective Michael addition

1,3-Dicarbonyl compounds warfarin anticoagulants

1,3-Dicarbonyl compounds, keto/enol

1,3-Dicarbonyl compounds, keto/enol tautomerism

1,3-Dicarbonyl type compounds carbon acidity

1,3-Dicarbonyl type compounds dianions

1,3-dicarbonyl compounds Michael reactions

1,3-dicarbonyl compounds cyclopropanation

1,3-dicarbonyl compounds enones

1,3-dicarbonyl compounds nitroalkenes

1- Diazo-2,5-dicarbonyl compounds

1.2- Diaminobenzenes, reaction with 1,2-dicarbonyl compounds

1.2- Dicarbonyl compounds

1.2- Dicarbonyl compounds

1.2- Dicarbonyl compounds Baeyer-Villiger reaction

1.2- Dicarbonyl compounds diazo-coupling reactions

1.2- Dicarbonyl compounds from 1,3-dithianes

1.2- Dicarbonyl compounds from acyl halides

1.2- Dicarbonyl compounds from alkenes

1.2- Dicarbonyl compounds from alkyl halides

1.2- Dicarbonyl compounds from alkynes

1.2- Dicarbonyl compounds from esters

1.2- Dicarbonyl compounds from imines

1.2- Dicarbonyl compounds from ketones

1.2- Dicarbonyl compounds furans from

1.2- Dicarbonyl compounds oxidation

1.2- Dicarbonyl compounds oxidative cleavage

1.2- Dicarbonyl compounds pyridazines from

1.2- Dicarbonyl compounds, formation

1.3- Dicarbonyl compounds a-alk-l-ynylation

1.3- Dicarbonyl compounds dianions

1.3- Dicarbonyl compounds dienolates

1.3- Dicarbonyl compounds from acetals

1.3- Dicarbonyl compounds from aldehydes

1.3- Dicarbonyl compounds from enamines

1.3- Dicarbonyl compounds from ketals

1.3- Dicarbonyl compounds from nitriles

1.3- Dicarbonyl compounds oxidations, manganese acetate

1.3- Dicarbonyl compounds selenenylation

1.3- Dicarbonyl compounds y-alkylation

1.3- Dicarbonyl compounds, 6-nitroHenry reaction intramolecular

1.3- Dicarbonyl compounds, alkylation

1.3- Dicarbonyl compounds, furans

1.3- Dicarbonyl compounds, oxidative

1.3- Dicarbonyl compounds, oxidative dimerization

1.3- Dicarbonyl compounds, reaction with amidines

1.3- Dicarbonyl compounds. See

1.3- dicarbonyl compounds amines

1.3- dicarbonyl compounds bonds

1.3- dicarbonyl compounds continued

1.3- dicarbonyl compounds cyclic

1.3- dicarbonyl compounds derivatives

1.3- dicarbonyl compounds ethers

1.3- dicarbonyl compounds nucleophiles

1.3- dicarbonyl compounds propargylation

1.3- dicarbonyl compounds reaction with

1.3- dicarbonyl compounds reaction with benzyl

1.3- dicarbonyl compounds reaction with benzylic

1.3- dicarbonyl compounds reaction with cycloalkene

1.3- dicarbonyl compounds reaction with phenyl

1.3- dicarbonyl compounds reaction with propargylic

1.3- dicarbonyl compounds reaction with tertiary

1.3- dicarbonyl compounds reaction with toluene

1.3- dicarbonyl compounds sulfide

1.3- dicarbonylic compounds

1.3- dicarbonylic compounds

1.4- Dicarbonyl compounds dehydrogenation

1.4- Dicarbonyl compounds from 2-ethyl-5-methyl

1.4- Dicarbonyl compounds from carboxylic acids

1.4- Dicarbonyl compounds from enolate anions

1.4- Dicarbonyl compounds from silyl enol ethers

1.4- Dicarbonyl compounds from unsaturated ketones

1.4- Dicarbonyl compounds use of cyclopropanes

1.4- Dicarbonyl compounds use of selenium dioxide

1.4- Dicarbonyl compounds via Wacker oxidation

1.4- Dicarbonyl compounds, Stetter reaction

1.4- Dicarbonyl compounds, reaction with hydrazines

1.4- dicarbonyl compounds, from succinic

1.5- Dicarbonyl compounds conjugate addition

1.5- Dicarbonyl compounds from hydrazones

1.5- Dicarbonyl compounds via Claisen rearrangement

1.5- Dicarbonyl compounds, synthesis Michael reaction

1.5- dicarbonyl compounds, cyclization

1.6- Dicarbonyl type compounds: synthesis

2-diazo-l,3-dicarbonyl compounds

5.6- Diaminopyrimidine, reaction with 1,2-dicarbonyl compounds

6-Dicarbonyl compounds enol form

A-Dicarbonyl compounds

Acyclic 1,4-dicarbonyl compounds

Acylation 5-dicarbonyl compounds

Aldosuloses and Other Dicarbonyl Compounds

Alkylation of 3-dicarbonyl compounds

Alkylation of p-dicarbonyl compounds

Allylation 1,3-dicarbonyl compounds

Allylation preparation of 1,4-dicarbonyl compounds

Amine-Catalyzed Cascade Reactions of Ketoses with 1,3-Dicarbonyl Compounds

Amines reactions with dicarbonyl compounds

Amino sugars 3-dicarbonyl compounds

Amino sugars reaction with /1-dicarbonyl compounds

Aniline derivatives dicarbonyl compounds

Aqueous 1,3-dicarbonyl compounds

Arginine reaction with dicarbonyl compound

Benzene with 1,2-dicarbonyl compounds

Benzyliden-1,3 -dicarbonyl compounds

Beta-dicarbonyl compounds

COPPER CATALYZED ARYLATION 0-DICARBONYL COMPOUNDS

Carbonyl compound dicarbonyl

Conjugate addition of 1,3-dicarbonyl compounds

Cyclization of 1.5-dicarbonyl compound

Cyclizations 4+3] Cycloadditions, 1,4-dicarbonyl compounds

Deoxy dicarbonyl compound

Detection dicarbonyl compounds

Diazomethane reaction with 1,2-dicarbonyl compounds

Diazotates 3-Dicarbonyl compounds

Dicarbonyl Compounds Claisen Condensations

Dicarbonyl Compounds and their Derivatives

Dicarbonyl Compounds as Nucleophiles

Dicarbonyl Compounds by Acylation of Ketone Enolates

Dicarbonyl Compounds with a-Amino Acids

Dicarbonyl Compounds, The Photochemistry of (Monroe)

Dicarbonyl Compounds, frames

Dicarbonyl and Related Compounds

Dicarbonyl compound aldol reactions with

Dicarbonyl compound reductions yeast

Dicarbonyl compound, reductive

Dicarbonyl compound, reductive coupling

Dicarbonyl compounds 2,4-disulfide

Dicarbonyl compounds Carbon dioxide

Dicarbonyl compounds Copper oxide

Dicarbonyl compounds Diacids

Dicarbonyl compounds Diketones

Dicarbonyl compounds Hexamethylphosphoric triamide

Dicarbonyl compounds Iodine

Dicarbonyl compounds Iodosylbenzene

Dicarbonyl compounds Iron carbonyl

Dicarbonyl compounds Keto amides

Dicarbonyl compounds Keto esters

Dicarbonyl compounds Knoevenagel reaction

Dicarbonyl compounds Methyl acetoacetate

Dicarbonyl compounds Methyl vinyl ketone

Dicarbonyl compounds Ozone

Dicarbonyl compounds Tebbe reagent

Dicarbonyl compounds Zinc chloride

Dicarbonyl compounds by oxidation

Dicarbonyl compounds decarboxylation

Dicarbonyl compounds fluorination

Dicarbonyl compounds from Claisen condensation

Dicarbonyl compounds malonates

Dicarbonyl compounds methylenation

Dicarbonyl compounds monoanions

Dicarbonyl compounds monoprotection

Dicarbonyl compounds product

Dicarbonyl compounds pyridones

Dicarbonyl compounds quinolines

Dicarbonyl compounds reaction with hydroxylamine

Dicarbonyl compounds reactions

Dicarbonyl compounds retrosynthetic analysis

Dicarbonyl compounds succinic anhydride

Dicarbonyl compounds tautomers

Dicarbonyl compounds, a-selenooxidative syn elimination

Dicarbonyl compounds, a-selenooxidative syn elimination synthesis

Dicarbonyl compounds, addition

Dicarbonyl compounds, addition reactions

Dicarbonyl compounds, addition transition metal complexes

Dicarbonyl compounds, aldol reactions

Dicarbonyl compounds, reduction

Dicarbonyl compounds, tautomerism

Dicarbonyl type compounds

Diels-Alder reaction 1,6-dicarbonyl compounds

Enamines dicarbonyl compound monoprotection

Enol ethers from 1,3-dicarbonyl compounds

Enolates 1.3- dicarbonyl compounds

Enolates of /3-dicarbonyl compounds

Enolates p-dicarbonyl compounds

Enols from 1,3-dicarbonyl compounds

Fi-dicarbonyl compound

From 1,3-Dicarbonyl Compounds and Ketones

From 1,5-Dicarbonyl Compounds

From l-Dicarbonyl Compounds

Fructose dicarbonyl compounds

Fructose reaction with dicarbonyl compounds

Ft-dicarbonyl compounds

Glyceraldehyde reaction with 1,3 dicarbonyl compounds

Glycoses, amino, reaction with /3-dicarbonyl compounds

Glycosylamines, reaction with /3-dicarbonyl compounds

Henry reaction 6-nitro-l,3-dicarbonyl compounds

Iron compounds Dicarbonyl

Isoxazoles from 1,3-dicarbonyl compound

J8-dicarbonyl compounds

Macrocyclic complexes with ligands based on 1,3-dicarbonyl compounds and 1,2- or 1,3-diamines

Methylene bis-dicarbonyl compounds

Methylene-1,3-dicarbonyl compound

Michael addition Of 1,3-dicarbonyl compounds

Monoprotection of Dicarbonyl Compounds

Other Dicarbonyl Compounds

Oxidation of Dicarbonyl Compounds to Carboxylic Acids

Oxidation of Ketones to a-Dicarbonyl Compounds

P-Dicarbonyl compounds

Phosphorylation 3-dicarbonyl compounds

Propanone dicarbonyl compounds

Pyrans from 1,3-dicarbonyl compounds

Pyrazines from 1,2-dicarbonyl compound

Pyridines from 1,3-dicarbonyl compound

Pyrimidines can be made from 1,3-dicarbonyl compounds and amidines

Pyrimidines from 1,3-dicarbonyl compound

Pyrrole synthesis, from 1,4-dicarbonyl compound

Pyrroles preparation from dicarbonyl compounds

Pyrroles, thiophenes, and furans from 1,4-dicarbonyl compounds

Pyryliums from 1,3-dicarbonyl compounds

Quinones and 1,2-Dicarbonyl Compounds (1,4-Dioxabutadienes)

Reaction of a,3-Dicarbonyl Compounds with Ammonia

Reduction of Functionalized Carbonyl and Dicarbonyl Compounds

Reductive cyclization dicarbonyl compounds

Retrosynthesis of 1,5-Dicarbonyl Compounds

Silylenes dicarbonyl compound monoprotection

Specific enol equivalents from 1,3-dicarbonyl compounds

Sulfinyl compounds, l,3-dicarbonyl-2-phenylpyrolysis

Syntheses Using 3-Dicarbonyl Compounds

Tautomeric 1,3-dicarbonyl compounds

Thioacetal-protected dicarbonyl compound

Thiophene, from 1,4-dicarbonyl compound

Thiophenes dicarbonyl compounds

Thiophenes preparation from dicarbonyl compounds

Unsaturated dicarbonyl compound

Vicinal dicarbonyl compounds

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