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Research Article Open access CC BY 3.0

Novel Routes to Biologically Active Enaminones, Dienoic Acid Amides, Arylazonicotinates and Dihydropyridazines under Microwave Irradiation

M. A. El-Apasery, S. M. Al-Mousawi, H. Mahmoud, M. H. Elnagdi

International Research Journal of Pure and Applied Chemistry · pp. 69–83 · Published 24 Aug 2011

10.9734/IRJPAC/2011/504

Abstract

Condensation of methylketones 1a,b with dimethylformamide dimethyl acetal (DMFDMA) without solvent in microwave oven afforded enaminones 2a,b, which reacted with malononitrile in ethanolic piperidine to yield dienoic acid amides 7a,b. In contrast, reactions of 2a,b with cyanoacetic acid resulted in the formation of pyranones 10. The pyranones were readily converted into 2-arylhydrazonoketones 13. Condensations of 13 with ethyl cyanoacetate afforded the 5-arylazonicotinates 17. Finally, 2-oxoarylhydrazonals 18 reacted with arylidenemalononitriles 19a,b in presence of chitosan to afford dihydropyridazines 21a,b. In addition the biological activity of the title compounds against Gram positive bacteria, Gram negative bacteria and Yeast were also evaluated.  

Enaminones arylhydrazonals arylazonicotinates pyridazines dihydropyridazines microwave heating chitosan

References (33)

  1. 1 Controlled Microwave Heating in Modern Organic Synthesis [DOI]
  2. 2 Synthesis of Heterocycles from Alkyl 3-(Dimethylamino)propenoates and Related Enaminones [DOI]
  3. 3 Hydrogen-bond acceptor properties of nitriles: a combined crystallographic andab initio theoretical investigation [DOI]
  4. 4 A Convenient One-Pot Preparative Method for 4,5-Diarylisoxazoles Involving Amine Exchange Reactions [DOI]
  5. 5 Enaminones as Building Blocks for the Synthesis of Substituted Pyrazoles with Antitumor and Antimicrobial Activities [DOI]
  6. 6 Enamines as Precursors to Polyfunctional Heteroaromatic Compounds; a Decade of Development [DOI]
  7. 7 Studies on enaminonitriles: A new synthesis of 1,3-substituted pyrazole-4-carbonitrile [DOI]
  8. 8 Synthesis, antibacterial and anticonvulsant evaluations of some cyclic enaminones [DOI]
  9. 9 Cyclopentathiadiazines, new heterocyclic materials from cyclic enaminonitriles [DOI]
  10. 10 Theoretical Insights into Material Properties of Schiff Bases and Related Azo Compounds [DOI]
  11. 11 Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydropyrimidines, Dihydropyridines, Triacylbenzenes and Naphthofurans under Microwave Irradiation [DOI]
  12. 12 Microwave-Assisted Synthesis of New Spiro[indoline-3,4′-quinoline] Derivatives via a One-Pot Multicomponent Reaction [DOI]
  13. 13 Reassignment of the structures of condensation products of α-keto α′-formylarylhydrazones with ethyl cyanoacetate: a novel route to ethyl 5-arylazo-2-hydroxynicotinates [DOI]
  14. 14 A convenient alternative route to β-aminoketones [DOI]
  15. 15 Carbon transfer reactions of functionalized oxazolidines and their open chain enamine tautomers to enamine nucleophiles. A facile synthesis of substituted pyridines and ring annulated derivatives [DOI]
  16. 16 Theoretical study of the static first hyperpolarizability of azo-enaminone compounds [DOI]
  17. 17 Cycloaddition reactions of cross-conjugated enaminones [DOI]
  18. 18 Synthesis of β-enaminones by ionic liquid catalysis: A one-pot condensation under solvent-free conditions [DOI]
  19. 19 Studies with Functionally Substituted Enamines: The Reactivity of Enaminals and Enamino Esters toward Naphthoquinone, Hydrazonoyl Halides, Aminoazoles and Hippuric Acid [DOI]
  20. 20 Zinc azaphthalocyanines with thiophen-2-yl, 5-methylthiophen-2-yl and pyridin-3-yl peripheral substituents: Additive substituent contributions to singlet oxygen production [DOI]
  21. 21 Structure of the intermediate in the synthesis of 6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile [DOI]
  22. 22 Enaminones as building blocks in organic syntheses: on the reaction of 3-dimethylamino-2-propenones with malononitrile [DOI]
  23. 23 A ratiometric hydrophilic fluorescent copolymer sensor based on benzimidazole chromophore for microbioreactors [DOI]
  24. 24 Fluorophilicity of alkyl and polyfluoroalkyl nicotinic acid ester prodrugs [DOI]
  25. 25 Reactivity, chemical selectivity and exhaust dyeing properties of dyes possessing a 2-chloro-4-methylthio-s-triazinyl reactive group [DOI]
  26. 26 Synthesis, reactions and antitumor activity of new β-aminovinyl 3-pyrazolyl ketones [DOI]
  27. 27 Synthesis and structure of α-azo-2-ketomethylquinolines [DOI]
  28. 28 Alkyl 2‐(2‐benzoyl‐2‐ethoxycarbonyl‐1‐ethenyl)amino‐3‐dimethylaminopropenoates in the synthesis of heterocyclic systems [DOI]
  29. 29 Synthesis of Azacarbazoles [DOI]
  30. 30 ChemInform Abstract: Benzyl and Heteroarylmethyl Carbanions: Structure and Substituent Effects [DOI]
  31. 31 Reactive dyes for cellulose. An unexpected hydrolysis product of a triazinyl reactive dye with a 3–carboxypyridine (nicotinic acid) leaving group [DOI]
  32. 32 Effects of γ-cyano substituent in allylic bridgehead solvolyses: evidence for cyano π conjugation in carbocations [DOI]
  33. 33 The catalytic effect of tertiary amines on the dyeing of monochlorotriazine dyes at high temperatures in a neutral medium [DOI]

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