Studies with Functionally Substituted Enamines: Synthesis of 2-Aroyl-3-dimethylamino-2-propenenitrile and Their Reactivity toward Nitrogen Nucleophiles

Abdelkhalik, Mervat Mohammed; Al-Qalaf, Fawzia; Al-Enezi, Amal; Al‐Ajmi, Johara Rashed

doi:10.3987/com-07-11196

Cited by 14 publications

(1 citation statement)

References 5 publications

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“…In previous work at our laboratories, we reported several efficient routes to polyfunctionally substituted heterocycles utilizing enaminones as starting materials [7,8,9,10,11]. We have also reported that the reaction of 1a with malononitrile in ethanolic sodium ethoxide afforded 2a in good yield [12], while reacting 1a-c with malononitrile in ethanolic piperidine was believed to afford 3a-c [13] (cf.…”

Section: Introductionmentioning

confidence: 99%

Enaminones as Building Blocks in Heterocyclic Syntheses: Reinvestigating the Product Structures of Enaminones with Malononitrile. A Novel Route to 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids

et al. 2008

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The reported structures of reaction products of enaminones with malononitrile in ethanolic piperidine are revised. A novel route to 2,3-dihydropyridazine-4-carboxylic acids 4a-c via reactions of 2-cyano-5-(dimethylamino)-5-arylpenta-2,4-dienamides 8a-c with nitrous acid or with benzenediazonium chloride is reported. Compounds 8a-c are converted to 1,2-dihydropyridine-3-carboxylic acid and 1,2-dihydropyridine-3-carbonitrile derivatives upon reflux in EtOH/ HCl and in AcOH.

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Section: Introductionmentioning

confidence: 99%

Enaminones as Building Blocks in Heterocyclic Syntheses: Reinvestigating the Product Structures of Enaminones with Malononitrile. A Novel Route to 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids

et al. 2008

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ChemInform Abstract: Studies with Functionally Substituted Enamines: Synthesis of 2‐Aroyl‐3‐dimethylamino‐2‐propenenitrile and Their Reactivity Toward Nitrogen Nucleophiles.

Al-Qalaf¹,

Abdelkhalik²,

Al-Enezi³

et al. 2008

ChemInform

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Fused pyrimidine derivatives R 0515Studies with Functionally Substituted Enamines: Synthesis of 2-Aroyl-3-dimethylamino-2-propenenitrile and Their Reactivity Toward Nitrogen Nucleophiles.-A facile and efficient synthesis of propenenitriles (IV) and their use as building blocks for some pyrazolopyrimidine and imidazopyrimidine derivatives are described.-(AL-QALAF, F.; ABDELKHALIK*, M. M.; AL-ENEZI, A.; AL-AJMI, J. R.; Heterocycles 75 (2008) 1, 145-156; Dep. Chem., Fac. Technol. Stud., Public Auth. Appl. Educ. Train., 13092 Safat, Kuwait; Eng.) -M. Bohle 22-163

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Poly(ethyleneglycol): A versatile and recyclable reaction medium in gaining access to benzo[4,5]imidazo[1,2‐a]pyrimidines under microwave heating

Wang

Hao

et al. 2009

Journal of Heterocyclic Chem

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Polyethylene glycol is found to be a nontoxic and recyclable reaction medium for the microwaveassisted, one-pot, multicomponent reactions of aromatic aldehydes with 2-aminobenzimidazole and 1,2-diphenylethanone in the presence of potassium carbonate. This environmentally friendly microwave protocol offers ease of operation and enables recyclability of reaction media and synthesis of a variety of substituted benzo [4,5]imidazo[1,2-a]pyrimidine derivatives. It is an efficient, promising, and green synthetic strategy to construct benzo [4,5]imidazo[1,2-a]pyrimidine skeleton.

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Studies with Functionally Substituted Enamines: Synthesis of 2-Aroyl-3-dimethylamino-2-propenenitrile and Their Reactivity toward Nitrogen Nucleophiles

Cited by 14 publications

References 5 publications

Enaminones as Building Blocks in Heterocyclic Syntheses: Reinvestigating the Product Structures of Enaminones with Malononitrile. A Novel Route to 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids

Enaminones as Building Blocks in Heterocyclic Syntheses: Reinvestigating the Product Structures of Enaminones with Malononitrile. A Novel Route to 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids

ChemInform Abstract: Studies with Functionally Substituted Enamines: Synthesis of 2‐Aroyl‐3‐dimethylamino‐2‐propenenitrile and Their Reactivity Toward Nitrogen Nucleophiles.

Poly(ethyleneglycol): A versatile and recyclable reaction medium in gaining access to benzo[4,5]imidazo[1,2‐a]pyrimidines under microwave heating

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