A New Approach for the Synthesis of Some Pyridine and Pyridone Derivatives

1983 ◽  
Vol 38 (12) ◽  
pp. 1690-1694 ◽  
Author(s):  
O. H. Hishmat ◽  
M. M. Y. Zohair ◽  
J. A. A. Miky
Keyword(s):  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
New Approach

Both visnaginone and khellinone react with malononitrile, ethyl cyanoacetate or cyanoacetamide in presence of ammonium acetate to give substituted furobenzopyrans or furobenzopyridones.However, the reaction of visnaginone and khellinone with aldehydes, and malononitrile in presence of ammonium acetate leads to the formation of the corresponding 2-amino-4,6-disubstituted pyridine 3-carbonitriles. The latter compounds are also obtained by treating the respective chalcones with malononitrile and ammonium acetate.3-Substituted 1,3-diketobutyrates form with malononitrile or with cyanoacetamide and ammonium acetate the 2-amino-4,6-disubstituted pyridine-3-carbonitriles or the 4,6-di-substituted cyanopyridones, respectively

scholarly journals The Cyclization of Ethyl Cyanoacetate and Ketones by Ammonium Acetate

1967 ◽  
Vol 40 (7) ◽  
pp. 1680-1684 ◽  
Author(s):  
Akio Sakurai ◽  
Hiroshi Midorikawa
Keyword(s):  
Ammonium Acetate ◽  
Ethyl Cyanoacetate

scholarly journals Uses of -diketones for the synthesis of novel heterocyclic compounds and their antitumor evaluations

2020 ◽  
Vol 34 (2) ◽  
pp. 385-405
Author(s):  
R. M. Mohareb ◽  
M. M. Kamel ◽  
Y. R. Milad
Keyword(s):  
Cell Lines ◽  
Ammonium Acetate ◽  
Benzimidazole Derivative ◽  
Ethyl Cyanoacetate ◽  
Pyridine Derivative ◽  
Active Compounds ◽  
Reference Drug ◽  
Thiophene Derivatives ◽  
Active Methylene ◽  
Dihydropyridine Derivatives

The reaction of the 3-oxo-N,3-diphenylpropan-amide (3) with either malononitrile or ethyl cyanoacetate in ammonium acetate gave the 1,2-dihydropyridine derivatives 6a or 6b, respectively. On the other hand, carrying the same reaction in the presence of triethylamine gave the 1,6-dihydropyridine derivatives 7a and 7b, respectively. Moreover, compound 3 reacted with 2-aminoprop-1-ene-1,1,3-tricarbonitrile to give the pyridine derivative 9. Compound 7b reacted with the active methylene derivatives 10a,b and 4a,b to give the naphthyridine derivatives 11a,b and 12a,b; respectively. Compound 3 was also used for the synthesis of thiophene derivatives 13a,b and 16a,b. In addition, the reaction of ethyl benzoylacetate (1) with o-phenylene diamine gave the benzimidazole derivative 18. The reactivity of the latter product towards different reagents was studied to give different products. The cytotoxicity of the newly synthesized products was studied towards some cancer and normal cell lines, in addition toxicity of compounds was measured and docking of the most active compounds was done. Compounds 6b, 7b, 9, 13a, 13b, 16a, 20b, 20c, 24b, 25 and 26b exhibited optimal cytotoxic effect against cancer tested cell lines. These active compounds were evaluated against c-Met kinase using foretinib as the reference drug where all compounds expressed higher activity than the reference drug.                     KEY WORDS: Ethyl benzoylacetate, Pyridine, Benzimidazole, Cytotoxicity   Bull. Chem. Soc. Ethiop. 2020, 34(2), 385-405 DOI: https://dx.doi.org/10.4314/bcse.v34i2.15

scholarly journals FSM-16-SO3H nanoparticles as a novel heterogeneous catalyst: preparation, characterization, and catalytic application in the synthesis of polyhydroquinolines

2018 ◽  
Vol 41 (3-4) ◽  
pp. 91-101 ◽  
Author(s):  
Somayeh Hashemi-Uderji ◽  
Mohammad Abdollahi-Alibeik ◽  
Reza Ranjbar-Karimi
Keyword(s):  
Room Temperature ◽  
Ammonium Acetate ◽  
Sol Gel ◽  
Ethyl Cyanoacetate ◽  
Textural Properties ◽  
High Catalytic Activity ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Catalytic Application

Abstract FSM-16-SO3H nanoparticles were prepared using a sol-gel method at room temperature. The prepared FSM-16-SO3H was used to catalyze the synthesis of polyhydroquinolines through a one-pot, four-component reaction of aldehydes, dimedone, ethyl cyanoacetate, and ammonium acetate under reflux condition in EtOH as a green solvent. To investigate the textural properties of the prepared catalyst, various techniques were applied such as X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscope, and Brunauer–Emmett–Teller. High catalytic activity, easy handling, and thermal stability are the superior properties that could be denoted after successive investigations of this catalyst. In addition, the catalyst can be recovered easily and reused effectively for several cycles.

scholarly journals Synthesis of some biologically active 2,4'-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety

2009 ◽  
Vol 74 (7) ◽  
pp. 733-743 ◽  
Author(s):  
T. Karabasanagouda ◽  
Vasudeva Adhikari ◽  
G. Parameshwarappa
Keyword(s):  
13C Nmr ◽  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
The Other ◽  
Mass Spectral Data ◽  
1H And 13C Nmr ◽  
Mass Spectral

A series of new 4-aryl-2'-[(4-hydroxyphenyl)thio]-6oxo-1,6-dihydro- 2,4'-bipyridine-5-carbonitriles (3a-k) and 6-amino-4aryl-2'-[(4-hydroxyphenyl) thio]-2,4'-bipyridine-5-carbonitriles (4a-h) were synthesized from 4-hydroxythiophenol (1). The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone (2). Further treatment of 2 with ethyl cyanoacetate in the presence of ammonium acetate with various aromatic aldehydes furnished the compounds 3a-k. On the other hand, condensation of 2 with aromatic aldehydes in the presence of alcoholic malononitrile in ammonium acetate gave compounds 4a-h. The structures of the newly synthesized compounds were established on the basis of their elemental analysis, as well as their IR, 1H- and 13C-NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

scholarly journals Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives

2009 ◽  
Vol 5 (1) ◽  
pp. 581-591 ◽  
Author(s):  
Kamelia El-mahdy ◽  
Azza El-Kazak ◽  
Mohamed Abdel-Megid ◽  
Magdy Seada ◽  
Osama Farouk
Keyword(s):  
Antimicrobial Activity ◽  
Carbon Disulfide ◽  
Elemental Analysis ◽  
Ethyl Acetoacetate ◽  
Ammonium Acetate ◽  
Oxalyl Chloride ◽  
Ethyl Cyanoacetate ◽  
Biological Evaluation ◽  
Phenyl Isothiocyanate ◽  
Pyrimidine Derivatives

10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolysis of carbaldehyde derivative 2 gave the hydrazone 9. Reaction of the latter with phenyl isothiocyanate afforded thiosemicarbazone 10, which underwent cyclization with oxalyl chloride to give thioxoimidazolidinedione 11. Condensation of compound 2 with thiosemicarbazide furnished thiosemicarbazone derivative 12. Reaction of compound 2 with aminopyrazolone in the presence of an acid and/or a base afforded pyrazolones 13 and 14. Treatment of carbaldehyde derivative 2 with cyanoacetohydrazide gave acrylohydrazide 15. Interaction of the latter with carbon disulfide yielded mercaptooxadiazole 16.  Condensation of compound 2 with acetylpyridazinone 17 produced chalcone 18. Reaction of  compound 18 with malononitrile in pyridine gave cyanopyran 19, while its reaction with malononitrile in presence of ammonium acetate in ethanol yielded cyanopyridine 20. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity. 

Synthesis of Pyranobenzopyranopyridines and Benzodipyran Derivatives

1986 ◽  
Vol 41 (2) ◽  
pp. 252-258 ◽  
Author(s):  
O. H. Hishmat ◽  
Kh. M. A. Khalil ◽  
Sh. I. El-Naem ◽  
A. H. Abd el-Rahman
Keyword(s):  
Ethyl Acetoacetate ◽  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
Acetyl Derivative ◽  
Reaction Condition ◽  
Bromo Derivative ◽  
Dihydroxy Derivative

6-Formyl-7-hydroxy-5-methoxy-2-methylchromone on bromination yields the 8-bromo derivative or the 8-bromo-6-formyl-5,7-dihydroxy derivative depending on the reaction condition. Cyclization of both leads to the corresponding 3-acetyl-, 3-benzoyl-, 3-carboxamido-, 3-carbethoxybenzodipyran derivatives.The 3-acetylbenzodipyran derivative when treated with ethyl acetoacetate or ethyl cyanoacetate in the presence of ammonium acetate yields the corresponding dihydropyranobenzopyranopyridine dione or the dihydropyranobenzopyranopyridine trione.The reaction of the 3-acetyl derivative with cyanoacetamide in the presence of ammonium acetate affords the substituted pyranobenzopyranopyridine dione.The 3-acetyl derivative undergoes self condensation to form the substituted benzopyranobenzopyran derivative.

The O–C diagrams of minor planets − a new approach to modelling the rotation

1999 ◽  
Vol 173 ◽  
pp. 185-188
Author(s):  
Gy. Szabó ◽  
K. Sárneczky ◽  
L.L. Kiss
Keyword(s):  
Error Analysis ◽  
Time Dependence ◽  
Theoretical Work ◽  
Minor Planet ◽  
Minor Planets ◽  
New Approach ◽  
Preliminary Results ◽  
Ccd Observations

AbstractA widely used tool in studying quasi-monoperiodic processes is the O–C diagram. This paper deals with the application of this diagram in minor planet studies. The main difference between our approach and the classical O–C diagram is that we transform the epoch (=time) dependence into the geocentric longitude domain. We outline a rotation modelling using this modified O–C and illustrate the abilities with detailed error analysis. The primary assumption, that the monotonity and the shape of this diagram is (almost) independent of the geometry of the asteroids is discussed and tested. The monotonity enables an unambiguous distinction between the prograde and retrograde rotation, thus the four-fold (or in some cases the two-fold) ambiguities can be avoided. This turned out to be the main advantage of the O–C examination. As an extension to the theoretical work, we present some preliminary results on 1727 Mette based on new CCD observations.

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