Heterocyclic Synthesis with Enamines: Convenient Syntheses of Polyfunctionally Substituted Pyrazole, Pyridine, Pyrimidine and Pyrazolo[3,4‐<i>d</i>]pyrimrdine Derivatives

Mohareb, Rafat M.; Sherif, Sherif Mourad; Zohdi, Hussein F.

doi:10.1002/jccs.199300026

Cited by 9 publications

(4 citation statements)

References 14 publications

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“…Further synthetic manipulation on this type of highly functionalized β-aminoenones provide feasibility to construct functionalized heterocyclic compounds, which further underscores the value of β-aminoenones formed by this protocol. For instance, the same products were reported, such as 3a reacted with hydrazinc hydrate, thiourea (i) and phenyl isothiocyanate (ii) leading to N -((3,5-dimethyl-4 H -pyrazol-4-ylidene)methyl)aniline ( 6 ), 3,5-dimethyl-4-((phenylamino)methylene)cyclohexa-2,5-diene-1-thione ( 7 ), and ( E )-1-(4-hydroxy-1-phenyl-6-(phenylimino)-1,6-dihydropyridin-3-yl)ethan-1-one, respectively ( 8 ) (Figure ).…”

supporting

confidence: 54%

Synthesis of β-Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

Zhou

Song

2018

Org. Lett.

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An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readily available starting materials to generate isocyanides in situ and sequentially fully converted to β-aminoenones, avoiding the generation of byproduct imines and overinsertion products. The mechanism study suggested that this method involves activation of two C(sp)-F bonds and the formation of isocyanides, which might nourish both isocyanide chemistry and fluorine chemistry.

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supporting

confidence: 54%

Synthesis of β-Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

Zhou

Song

2018

Org. Lett.

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“…The starting key reagent 4-aminoantipyrine was purchased from Sigma-Aldrich chemical company (St. Louis, MO, USA). In this work, the reactivity of 4-aminoantipyrine with active methylene containing compounds (malononitrile, 2-(ethoxymethylene)malononitrile, ethylcyanoacetate, (ethoxymethylene)ethylcyanoacetate and acetylacetone) was studied and the reaction proceeded in the presence of triethylorthoformate in methanol containing catalytic amounts of acetic acid following the reported reaction condition [ 19 ]. The obtained pyrazolone derivatives 2 – 4 , respectively, were identified by elemental and spectral data.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles

Ghorab

El‐Gazzar²,

Alsaid

2014

IJMS

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4-Aminoantipyrine was utilized as key intermediate for the synthesis of pyrazolone derivatives bearing biologically active moieties. The newly synthesized compounds were characterized by IR, 1H- and 13C-NMR spectral and microanalytical studies. The compounds were screened as anticancer agents against a human tumor breast cancer cell line MCF7, and the results showed that (Z)-4-((3-amino-5-imino-1-phenyl-1H-pyrazol-4(5H)-ylidene)methylamino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 5, 3-(4-bromophenyl) -1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 13, 1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1-Hpyrazol- 4-yl)-3-(4-iodophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 14, 3,3′-(4,4′-sulfonylbis(4,1-phenylene))bis(1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol- 4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile) 16, (Z)-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-hydrazono-4-oxo-3-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 17, (Z)-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-3-phenyl-2-(2-phenylhydrazono)-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile 18, and (Z)-4-(3-amino-6-hydrazono-7-phenyl-6,7-dihydro pyrazolo[3,4-d]pyrimidin-5-yl)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 19 were the most active compounds with IC50 values ranging from 30.68 to 60.72 μM compared with Doxorubicin as positive control with the IC50 value 71.8 μM.

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“…Enamines are one of the most dynamic areas in heterocyclic synthesis . They represent a class of vinyl–heteroatom derivatives that can be prepared via condensation of active methylene ketones with N , N ‐dimethylformamide dimethylacetal (DMF‐DMA) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Bis(enaminones) as Versatile Precursors for Novel Bis([1,2,4]triazolo[1,5‐a]pyrimidines) and Bis(2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1H)‐ones)

Fares

Mekky

Abdelhamid

et al. 2019

Journal of Heterocyclic Chem

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Heterocyclic Synthesis with Enamines: Convenient Syntheses of Polyfunctionally Substituted Pyrazole, Pyridine, Pyrimidine and Pyrazolo[3,4‐d]pyrimrdine Derivatives

Cited by 9 publications

References 14 publications

Synthesis of β-Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

Synthesis of β-Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

Synthesis, Characterization and Anti-Breast Cancer Activity of New 4-Aminoantipyrine-Based Heterocycles

Bis(enaminones) as Versatile Precursors for Novel Bis([1,2,4]triazolo[1,5‐a]pyrimidines) and Bis(2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1H)‐ones)

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