Recyclisation of carbo- and heterocyclic compounds involving malononitrile and its derivatives

Литвинов, В. П.

doi:10.1070/rc1999v068n01abeh000273

Cited by 20 publications

(3 citation statements)

References 108 publications

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“…66 The yield of a dimer 14 is highly dependent on the reaction conditions. While in some cases the ylidene dimerization is significant and the by-product is isolated in higher yield than the desired 2-aminothiophene derivative 58 , on other hand under suitable reaction conditions not only is the straightforward reaction favored, but also the recyclization of dimerized ylidene 14 to appropriate aminothiophene 7 occurs.…”

Section: Dimerization Vs Cyclizationmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

178

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Chemistry of 2-aminothiophenes is arguably one of the most extensive and dynamic field of present-day thiophene research. Since 1961 when first report on the Gewald reaction was reported it became a universal method for synthesis of substituted 2-aminothiophenes and has gained prominence in recent times. The availability of reagents and the mild reaction conditions all contribute to the versatility of this reaction. This review summarizes the synthetic strategies for substituted 2-aminothiophenes. Consequently, details about the proposed mechanism of Gewald-like reactions and the wide scope of substituted 2-aminothiophenes for real life applications.

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Section: Dimerization Vs Cyclizationmentioning

confidence: 99%

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Puterová¹,

Krutošíková²,

Végh³

2010

Arkivoc

178

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“…with active methylene group. These compounds together with nitrile groups have great synthetic potentials and through changing the structure of other reagents that react with them it is possible to synthesize many structured complex carbo and heterocyclic compounds [6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Molecular Crystalline Structure of Ethyl-1- Acetyl-3-(4-Chlorophenyl) -2,2-Dicyanocyclopropane Carboxylate

Ismiyev¹,

Hajiyeva²,

Аскеров³

et al. 2018

Chemical Problems

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Three-component condensation reaction of malonodinitrile, 4-chloro-benzaldehyde and ethyl 4chloro-3-oxobutanoate has been analyzed to establish that in the presence of NaOH base, the reaction proceeds by Knoevenagel-Michael-Perkin cascade carbocyclization to form ethyl-1acetyl-3-(4-chlorophenyl)-2,2-dicyanocyclopropane carboxylate. The structure of the reaction product examined through with X-ray analysis

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“…Recyclizations involve rearrangement of the heterocyclic skeleton, replacement of heteroatoms, ring contraction or expansion, or isomerization [1]. Recyclizations are complex transformations including ring opening and closure of new ring, whereas from the preparative viewpoint they are conventional onestep processes.…”

mentioning

confidence: 99%

Recyclization of 1,3-dialkyl-6-nitro-1H-imidazo[4,5-b]pyridine-2,5(3H,4H)-diones into imidazole derivatives

Lomov

2016

Russ J Org Chem

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Treatment of 5-amino-1,3-dialkyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones with sodium nitrite in aqueous HCl gave 1,3-dialkyl-1H-imidazo[4,5-b]pyridine-2,5(3H,4H)-diones which were nitrated with potassium nitrate in sulfuric acid to 6-nitro derivatives, and the latter underwent recyclization into 4-amino-1,3dialkyl-5-(1H-pyrazol-5-yl)-2,3-dihydro-1H-imidazol-2-ones by the action of hydrazine hydrate. R = Me (a), Et (b).

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Recyclisation of carbo- and heterocyclic compounds involving malononitrile and its derivatives

Cited by 20 publications

References 108 publications

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

The Synthesis and Molecular Crystalline Structure of Ethyl-1- Acetyl-3-(4-Chlorophenyl) -2,2-Dicyanocyclopropane Carboxylate

Recyclization of 1,3-dialkyl-6-nitro-1H-imidazo[4,5-b]pyridine-2,5(3H,4H)-diones into imidazole derivatives

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