Reaction Of Azomethine Ylides Research Articles

A Clean and Expedient Synthesis of Pyrido[1,4]oxazepino Spiropyrrolidines Through One-Pot, Three-Component [3 + 2] Cycloaddition Reaction

One-pot three component synthesis of novel pyrido[1,4]-oxazepine fused spiropyrrolidines has been accomplished in good yields by 1,3-dipolar cycloaddition reaction of azomethine ylide, derived from paraformaldehyde and sarcosine with (E)-4-benzylidene-hexahydro-1H-pyrido[2,1-c][1,4]-oxazepine-3(7H)-one as dipolarophiles derived from Baylis-Hillman adducts. The effect of solvent on the [3 + 2]-cycloaddition reaction is also studied.

Synthesis of Chlorin-Fused Monospirooxindolopyrrolidines Through a Facile [3 + 2]-Cycloaddition of Azomethine Ylides

One-pot synthesis of novel chlorin-fused monospirooxindolopyrrolidines has been accomplished in good yield via a facile [3 + 2]-cycloaddition reaction of azomethine ylides, derived from isatin/N-benzylisatin and sarcosine, with various porphyrin derivatives as dipolarophiles.

Expedient Synthesis of N-Fused Indoles through an Intramolecular [3+2]-Cycloaddition Approach

A variety of N-fused indolo pyrrolo-pyrroles and pyrrolo-pyrrolizidines were synthesized by intramolecular 1,3-dipolar cycloaddition reaction of azomethine ylide generated from N-alkenylindole carbaldehyde which were prepared by the N-alkylation of indole 2-aldehyde with Baylis-Hillman bromides.

Expedient Synthesis of C-3-Ferrocenoyl-N-methylpyrrolidines via [3 + 2]-Cycloaddition Reaction of Azomethine Ylides

A facile synthesis of C-3-ferrocenoyl-N-methylpyrrolidines through [3 + 2]-cycloaddition reaction of azomethine ylides is described.

A Facile One-Pot Three-Component Synthesis of Macrocyclic Imidazolidines by [3+2] Cycloaddition Reaction of Azomethine Ylides

One-pot three-component synthesis of novel macrocyclic imidazolidines has been accomplished in good yields via a facile [3+2] cycloaddition reaction of azomethine ylide, derived from paraformaldehyde and sarcosine, with various macrocyclic imines as dipolarophiles. The effect of solvent on the [3+2]-dipolar cycloaddition reaction is also studied.

Stereoselective [3 + 2] Cycloaddition Reactions of Azomethine Ylides Derived from 5-Methylbenzo[B]thiophene-2,3-dione and Piperidine-2-Carboxylic Acid

A series of spiropyrrolidines have been synthesized in 68–76% yield by 1,3 dipolar cycloaddition reaction of azomethine ylides generated by a decarboxylative route from 5-methylbenzo[b]thiophene and piperidine-2-carboxylic acid with different acetylenic and ethylenic dipolarophiles. The stereochemical course of the cycloaddition has been investigated by spectral data and AM1 quantum chemical method. The novel spiro compounds have been characterized by elemental analyses and spectroscopic techniques.

Enantioselective 1,3-Dipolar Cycloadditions with Silver Catalysts

The 1,3-dipolar cycloaddition reaction can generate four stereocenters with defined stereochemistry in a single step. The authors report on the reaction of azomethine ylides with N-methylmaleimide as dipolarophile in the presence of a chiral silver catalyst. The catalyst itself is insoluble in the reaction solvent and can be recovered and used consecutively up to four times with minimal loss in activity and selectivity.

One pot synthesis of novel dispiro[oxindole‐thiazolidinedione/thioxo‐thiazolidinone/dihydro pyrazolone]‐pyrrolidines via 1,3‐dipolar cycloaddition reaction of azomethine ylides

Abstractmagnified imageA series of novel dispiro[oxindole‐thiazolidinedione]pyrrolidine, dispiro[oxindole‐thioxothiazolidinone]‐pyrrolidine, dispiro[oxindole‐dihydro‐pyrazolone]pyrrolidine were synthesized by both regio‐ and stereo‐selective 1,3‐dipolar cycloaddition reaction of azomethine ylide generated from amino acid and amino acid ester with π‐deficient alkenes in a single pot protocol in good yield. X‐ ray crystallographic studies established orthogonal disposition between spiro‐oxindole and spiro‐thiazolidinedione rings in 4a and 5a.

Novel Synthesis of N‐Methyl Spiropyrrolidines by 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides

A series of novel N‐methyl spiropyrrolidines have been synthesized in good yield by the cycloaddition reaction of azomethine ylides generated by a decarboxylative route from sarcosine and paraformaldehyde with conformationally locked s‐trans enone functionality present in the (E)‐3‐arylidene‐4‐chromanone as dipolarophiles. The structure of the title compound was established by spectroscopic techniques.

1,3-Dipolar Cycloaddition Reactions of Porphyrins with Azomethine Ylides

[reaction: see text] The behavior of porphyrins as dipolarophiles in 1,3-dipolar cycloadditions with azomethine ylides was studied. Depending on the nature of the substituent groups on the porphyrin macrocycles, the reaction can give monoadducts (chlorins) or bisadducts (isobacteriochlorins and bacteriochlorins). When a large excess of azomethine ylide is used, trisadducts can also be obtained. Mixed isobacteriochlorin derivatives were prepared from the reaction of azomethine ylides with the chlorin monoadducts previously obtained via Diels-Alder reactions.

One-pot highly diastereoselective synthesis of some novel spiro pyrrolizidines via 1,3-dipolar cycloaddition reaction of azomethine ylide

Indenoquinoxaline-11-one derivatives react with proline and N-aryl maleimides via decarboxylative azomethine ylide formation and subsequent 1,3-dipolar cycloaddition involving an exo- transition state to give new heterocyclic adducts in 71–94% yields.

A New Access to Dispiro 7-Oxaindazolidines Spiroxindole Derivatives

Synthesis of dispiro 7-oxaindazolidines has been accomplished by regioselective 1,3-dipoiar cycloaddition reaction of azomethine ylide generated from secondary amine, morpholine, and isatin (via deprotonation route) with arylidene chromanones and arylidene tetralones as dipolarophiles.

A Novel Entry into a New Class of Dispiroheterocycles Through Azomethine Ylides Involving Unusual Dipolarophiles

The cycloaddition reaction of azomethine ylides towards (E)-3-arylidene-4-chromanone as new dipolarophile has been investigated. High degree of regioselectivity has been observed in the synthesis of a new class of functionalized dispiroheterocyclic pyrrolidines bearing chromanone and acenaphthenequinone framework.

Asymmetric 1,3-dipolar cycloaddition of N-metalated azomethine ylides to methyl (S)-2-(p-tolylsulfinyl)acrylate. Synthesis of optically pure 2,4,5-trisubstituted 2,5-dihydro-1H-pyrroles.

The first 1,3-dipolar reaction of azomethine ylides with optically pure vinyl sulfoxide are reported. The presence of the sulfinyl group increase the reactivity of the acrylate moiety as a dipolarophile, and the reactions evolve with complete regio- and endo-selectivities. Nevertheless, mixtures of the two diastereoisomers 4 and 5 (75-88% de) resulting from the anti dipole/s-cis dipolarophile and syn dipole/s-trans dipolarophile approaches, respectively, are obtained. The stereoselectivity can be controlled by using THF or MeCN as solvents or by changing the reaction temperature in MeCN. After separation of the cycloadducts, optically pure 2,5-dihydro-1H-pyrroles are easily obtained by pyrolytic desulfinylation.

A FORMAL [3 + 2] CYCLOADDITION STRATEGY FOR THE SYNTHESIS OF UNIQUE CLASS OF DISPIROHETEROCYCLES

Novel dispiropyrrolidines and dispiropyrrazolidines have been prepared in good yields using highly regioselective cycloaddition reaction of azomethine ylides with diversely substituted (E)-3-arylidene-chroman-4-ones.

ChemInform Abstract: Formation and Reaction of Azomethine Ylide by the Reaction of Cu(acac) 2‐Ketocarbenoids with 1,1‐Diphenylmethanimine.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Formation and Reaction of Azomethine Ylide by the Reaction of Cu(acac)2- ketocarbenoids with 1,1-Diphenylmethanimine

Abstract The reaction of α-diazocarbonyl compounds with 1,1-diphenylmethanimine in the presence of Cu(acac)2 afforded the corresponding N-substituted imines in general together with pyrrolidine and 1,4,6-dioxazocine derivatives (in the reaction of α diazo-4-chloroacetophenone) and 1,1-diphenyl-2-(4-nitrobenzoyl) ethylene (in the reaction of α-diazo-4-nitroacetophenone) through azomethine ylides.

ChemInform Abstract: Chiral Mn(II) and Co(II) Catalysts for the 1,3‐Dipolar Cycloaddition Reactions of Azomethine Ylides Derived from Arylidene Imines of Glycine.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Dipolar Cycloaddition Reactions of Azomethine Ylides for the Synthesis of Polyhydroxypyrrolidines as Potential Enzymatic Inhibitors.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.