Heterocyclic Synthesis via Enaminonitriles: One-pot Synthesis of Some New Pyrazole, Isoxazole, Pyrimidine, Pyrazolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole and Pyrido[1,2-a]benzimidazole Derivatives

Dawood, Kamal M.; Farag, Ahmad M.; Kandeel, Zaghloul E.

doi:10.1039/a807428c

Cited by 29 publications

(22 citation statements)

References 4 publications

(4 reference statements)

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“…3 Recently, β-dimethylamino-α,β-unsaturated ketones and nitriles have been transformed into pyridine, isoquinoline, 4 pyrazole, isoxazole, pyrimidine, 5 and pyranone derivatives. 6 In this connection, we have previously reported a 3 step preparation of (Z)-3-benzoylamino-4-dimethylamino-2-oxo-3-butene 1 from hippuric acid and cyclizations of the enaminone 1 into pyrazole and pyrido [2,3-d]pyrimidine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Transformations of (Z)-2-benzoylamino-4-dimethylamino-2-oxo-3-butene and (E)-3-benzoylamino-4-cyano-2-oxo-3-butene into pyrimidine, pyrazole and isoxazole derivatives

Bratusek¹,

Meden²,

Svete³

et al. 2003

Arkivoc

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Reaction of (Z)-2-Benzoylamino-4-dimethylamino-2-oxo-3-butene 1 with amidines 2a-e afforded pyrimidines 3a-e. Acid-catalysed treatment of 1 with potassium cyanide gave (E)-3-benzoylamino-4-cyano-2-oxo-3-butene 4. 1,3-Dipolar cycloadditions of nitrile imines and 2,4,6-trimethoxybenzonitrile oxide 7a to compound 4 afforded the corresponding pyrazole derivatives 6a-d and the isoxazole-4-carbonitrile 8a. In the reaction of 4 with 2,4,6-trimethylbenzonitrile oxide 7b, bis-cycloadduct 9 was formed and its structure was also determined by X-Ray analysis.

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Section: Introductionmentioning

confidence: 99%

Transformations of (Z)-2-benzoylamino-4-dimethylamino-2-oxo-3-butene and (E)-3-benzoylamino-4-cyano-2-oxo-3-butene into pyrimidine, pyrazole and isoxazole derivatives

Bratusek¹,

Meden²,

Svete³

et al. 2003

Arkivoc

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“…Approaches for the synthesis of benzimidazo[1,2-a] pyrimidine derivatives generally involve using harsh dehydrating reaction conditions [8,[25][26][27][28][29][30]. These reactions are often carried out under high pressure and require long reaction time.…”

Section: Resultsmentioning

confidence: 99%

Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a] pyrimidines and their antimicrobial activities

et al. 2009

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Comparative studies were performed on a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a]pyrimidines, which were synthesized with conventional and microwave heating methods. In microwave irradiation method, approximately, 95–97.5% of the reaction time was increased and 1–45% yield increase was obtained. All compounds were able to inhibit the growth of the screened microorganisms in vitro with MIC values between 3.9–250 μg mL−1. The highest activity was expressed by compound IIId (2,4-diphenyl-benzo[4,5]imidazo[1,2-a] pyrimidine), which has the MIC value of 3.9 μg mL−1 and 31.2 μg mL-1 for Penicillium natatum ATCC 24791 and E. faecalis ATCC 29212, respectively.

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“…Many synthetic methods are available for the construction of the pyrazole heterocyclic core, and some of these have been improved with microwave irradiation [249][250][251]. reactor gave pyrazole 160 in 87% yield and 94% purity, as determined by LC/MS (Fig.…”

Section: Pyrazolesmentioning

confidence: 99%

Recent Advances in Microwave-Assisted Synthesis of Heterocyclic Compounds

Molteni¹,

Ellis²

2005

COS

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Heterocyclic Synthesis via Enaminonitriles: One-pot Synthesis of Some New Pyrazole, Isoxazole, Pyrimidine, Pyrazolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole and Pyrido[1,2-a]benzimidazole Derivatives

Cited by 29 publications

References 4 publications

Transformations of (Z)-2-benzoylamino-4-dimethylamino-2-oxo-3-butene and (E)-3-benzoylamino-4-cyano-2-oxo-3-butene into pyrimidine, pyrazole and isoxazole derivatives

Transformations of (Z)-2-benzoylamino-4-dimethylamino-2-oxo-3-butene and (E)-3-benzoylamino-4-cyano-2-oxo-3-butene into pyrimidine, pyrazole and isoxazole derivatives

Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a] pyrimidines and their antimicrobial activities

Recent Advances in Microwave-Assisted Synthesis of Heterocyclic Compounds

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