Reaction of Aliphatic Amines with Acetoacetanilide in the Presence of Zeolite Catalyst. Solvent-Free Synthesis of Symmetric N,N‘-Dialkylureas

Bigi, Franca; Frullanti, Bettina; Maggi, Raimondo; Sartori, Giovanni; Zambonin, Elena

doi:10.1021/jo981109g

Cited by 33 publications

(17 citation statements)

References 21 publications

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“…It has been found that 2-aminopyridine was fused with ethyl acetoacetate for two hours to yield N-2-pyridyl-3-oxobutanamide (1) [6,7]. However, when the reaction time was increased to 5 hours a product with a molecular formula C 9 H 8 N 2 O and molecular weight 160 was obtained.…”

Section: Resultsmentioning

confidence: 99%

“…IR spectra (KBr) were recorded on a FTIR 5300 spectrometer (, cm -1 ). The 1 H NMR spectra were recorded in DMSO-d 6 and CDCl 3 at 200 MHz on a Varian Gemini NMR spectrometer (, ppm) using TMS as an internal standard. Mass spectra were obtained on GC Ms-QP 1000 EX mass spectrometer at 70 ev.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction mixture was allowed to cool and treated with petroleum ether (40-60), the solid product, so formed, was collected by filtration and crystallized from ethanol. It was obtained as colorless crystals (50%); mp 162-164°C;  max /cm -1 (KBr) 3150 (NH), 1651 (C=O);  H (DMSO-d 6 …”

Section: Preparation O F 12-dihydro-4-methyl[18]naphthyridine-2-onementioning

confidence: 99%

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Utility of N-2-Pyridyl–3-Oxobutanamide in Heterocyclic Synthesis: Synthesis of New Dihydropyridine, Fused Pyridine, Pyridopyridone, Pyridazine and Pyridopyrimidinethione Derivatives

Hafiz

Khodair

Baker

et al. 2008

Al-Azhar Bulletin of Science

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Abstract2-Aminopyridine was fused with ethyl acetoacetate for two hours to yield the N-2-pyridyl-3-oxobutanamide (1). However, when the reaction time was increased to 5 hours compound 3 was obtained. Condensation of 3 with benzaldehyde gave 4. The reaction of pyridopyridone 3 with arylidenemalononitrile 7a-c afforded 4H-pyran derivatives 10a-c. In contrast to the behavior of arylidenemalononitriles 7a-c towards pyridopyridine 3, benzylidenemalononitrile 7d reacted with compound 3 to give the product 11. Compound 1 was allowed to react with arylidenemalononitriles to give the dihydropyridine derivatives 17a-d. Alkylation of compound 1 with alkylating agents has been also reported. Thus, compound 1 was condensed with [DMF-DMA] in refluxing dioxane to yield 18, but under the reaction conditions we obtained only 21. The pyridopyridone 3 reacted with benzoyl isothiocyanates 25a,b to give thiourea derivatives 26a,b. Cyclization of 26a,b in dry dioxane and conc. sulphuric acid afforded pyridopyrimidine-2-thione derivatives 27a,b. On the other hand, coupling of pyridopyridone 3 with the aryl diazonium salts 28a-e afforded the corresponding azo products 29a-e. Boiling of compound 29 in ethanol and HCl afforded the azo products 30a-e. Treatment of arylhydrazone 30a with malononitrile afforded the pyridazine derivative 31.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Utility of N-2-Pyridyl–3-Oxobutanamide in Heterocyclic Synthesis: Synthesis of New Dihydropyridine, Fused Pyridine, Pyridopyridone, Pyridazine and Pyridopyrimidinethione Derivatives

Hafiz

Khodair

Baker

et al. 2008

Al-Azhar Bulletin of Science

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“…So it has been found that reactions of β-oxoanilide 1 (prepared as literature procedure) 9 reacted with acetyl isothiocyanate 2a in refluxing dry acetone afforded the unexpected pyridine derivative 6a rather than the expected pyrimidine derivative 4a. Structure 6a was assigned for the reaction product based on spectroscopic data (IR, 1 H NMR and 13 C NMR).…”

Section: Resultsmentioning

confidence: 99%

-Oxoanilide as Building Blocks in Heterocyclic Synthesis: A New Synthesis of Polyfunctionally Substituted Pyridines, Pyrans and Pyrimidines

Hussein

Khames

El-Adasy

et al. 2011

Al-Azhar Bulletin of Science

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Abstractβ-Oxoanilide 1 reacted with acetyl isothiocyanate and ethoxycarbonyl isothiocyanate to give pyridine derivatives 6a,b and pyrimidinethiol 8 respectively. While with arylidine malononitrile gave the pyran derivative 12. Similarly, treatment of 1 with arylidine cyanoacetamide or arylidine cyanothioacetamide afforded the pyridine derivatives 13a,b, 14a,b respectively. Condensation of 1 with aromatic aldehyde obtained the cyclohexenones 19a-c. The reaction of 1 with a mixture of aromatic aldehyde and urea or thiourea gave the pyrimidine derivatives 23a,b. Treatment of compound 1 with arylidine acetophenone yield the cyclohexene derivatives 26a,b. Reaction of 1 with a mixture of ethyl cyanoacetate and sulfur yield the thiophene derivative 27. Which was reacted with formamide, potassium thiocyanate and hydrazine to afford the thienopyrimidines 28, 29 and the hydrazide derivative 30. respectively.

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“…50 to 90%. 18 Based on earlier work, [126] a method has been developed to convert acetoacetanilides into unsymmetrical ureas. This reaction involves treating the acetoanilide with a stoichiometric amount of a primary or secondary aliphatic amine or an aromatic amine at 120 8 8Cin xylene in the absence of any additional reagent (Scheme 42).…”

Section: Scheme 39 Strategies For Urea Synthesis Involving the Use Ofmentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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Reaction of Aliphatic Amines with Acetoacetanilide in the Presence of Zeolite Catalyst. Solvent-Free Synthesis of Symmetric N,N‘-Dialkylureas

Cited by 33 publications

References 21 publications

Utility of N-2-Pyridyl–3-Oxobutanamide in Heterocyclic Synthesis: Synthesis of New Dihydropyridine, Fused Pyridine, Pyridopyridone, Pyridazine and Pyridopyrimidinethione Derivatives

Utility of N-2-Pyridyl–3-Oxobutanamide in Heterocyclic Synthesis: Synthesis of New Dihydropyridine, Fused Pyridine, Pyridopyridone, Pyridazine and Pyridopyrimidinethione Derivatives

-Oxoanilide as Building Blocks in Heterocyclic Synthesis: A New Synthesis of Polyfunctionally Substituted Pyridines, Pyrans and Pyrimidines

Acyclic and Cyclic Ureas (Update 2013)

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