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.

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. 

scholarly journals Mo@GAA-Fe3O4 MNPs: a highly efficient and environmentally friendly heterogeneous magnetic nanocatalyst for the synthesis of polyhydroquinoline derivatives

RSC Advances ◽  
2021 ◽  
Vol 11 (18) ◽  
pp. 10497-10511
Author(s):  
Mehraneh Aghaei-Hashjin ◽  
Asieh Yahyazadeh ◽  
Esmayeel Abbaspour-Gilandeh
Keyword(s):  
Ethyl Acetoacetate ◽  
Ammonium Acetate ◽  
Environmentally Friendly ◽  
Magnetic Nanocatalyst ◽  
Methyl Acetoacetate ◽  
Highly Efficient ◽  
Fe3o4 Mnps

Polyhydroquinolines were obtained from a sequential four-component reaction between dimedone or 1,3-cyclohexandione, ethyl acetoacetate, or methyl acetoacetate as a β-ketoester, aldehydes, and ammonium acetate, with Mo@GAA-Fe3O4 MNPs as a green nanocatalyst.

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

Process Research of 1-(3,4-Dichloropheny)-3-Methyl-Pyrazolone-5-one Synthesis

2012 ◽  
Vol 450-451 ◽  
pp. 223-227 ◽  
Author(s):  
Hui Qun Yu ◽  
You Bin Mo ◽  
Yan Fang Liao ◽  
Hai Zhou ◽  
Zhi Peng He
Keyword(s):  
Aqueous Medium ◽  
Ethyl Acetoacetate ◽  
Process Research ◽  
Raw Material ◽  
Reaction Condition ◽  
Phenylhydrazine Hydrochloride ◽  
New Process ◽  
Optimal Reaction Condition ◽  
Optimal Reaction ◽  
Chromatographic Purity

The new process of 1-(3,4-dichloropheny)-3-methyl-pyrazolone-5-one (34DCPMP) synthesis had been discovered, which using 3,4-dichloro phenylhydrazine hydrochloride(DCPH) and ethyl acetoacetate as the raw material , The product was obtained by the route during cyclization in aqueous medium. The structure of products was confirmed by 1HNMR, 13CNMR and IR. The effects of factors on the yield of products were investigated. It was found that the yield of 34DCPMP can reach 98.7% under the optimal reaction condition of n(34DCPH):n(ethyl acetoacetate) with 1:1.1, n(34DCPH):n(Na2SO3) with 1.3:1 at 80°C, and pH 7.5 for 3h. The chromatographic purity can be higher than 98.2%.

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

1968 ◽  
Vol 41 (1) ◽  
pp. 165-167 ◽  
Author(s):  
Akio Sakurai ◽  
Hiroshi Midorikawa
Keyword(s):  
Ethyl Acetoacetate ◽  
Ammonium Acetate

Synthesis of cyano derivatives with diazaquaterphenyl skeleton

1985 ◽  
Vol 50 (8) ◽  
pp. 1870-1877 ◽  
Author(s):  
Štefan Marchalín ◽  
Josef Kuthan
Keyword(s):  
Ammonium Acetate ◽  
Acetyl Derivative ◽  
Analogous Reaction

Cyclocondensation of 3-aryl-2-arylmethylene-3-oxopropanenitriles I with 4,4'-diacetylbiphenyl (II) in the presence of ammonium acetate gives para-substituted 4''-acetyl-3,5-diphenyl-2-aza-1:1',4':1''-terphenyls III and 4,4'''-dicyano-3,3''',5,5'''-tetraphenyl-2,2'''-diaza-1:1',4':1'',4'':1'''-quaterphenyls IV. Analogous reaction of the acetyl derivative IIIe with the oxonitriles Ie and Ia afforded the corresponding products IVe and V.

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

Reactions of ferrocenyl chalcones with hydrazines and active methylene compounds

2016 ◽  
Vol 22 (2) ◽  
pp. 69-77 ◽  
Author(s):  
Marwa El-Hussieny ◽  
Hisham Abdallah A. Yosef ◽  
Mohamed R.H. Mahran ◽  
Nabila M. Ibrahim
Keyword(s):  
Hydrazine Hydrate ◽  
Reaction Mechanisms ◽  
Ethyl Acetoacetate ◽  
New Products ◽  
Ethyl Cyanoacetate ◽  
Spectroscopic Methods ◽  
Phenyl Hydrazine ◽  
Active Methylene Compounds ◽  
Ferrocenyl Chalcones ◽  
Active Methylene

AbstractClaisen-Schmidt condensation of ferrocenecarboxaldehyde (2b) with 2-acetylfuran (4) yielded (E)-3-ferrocenyl-1-(2-furyl)prop-2-en-1-one (E-5) together with 1,5-di(2-furyl)-3-ferrocenylpentane-1,5-dione (6). Reactions of the ferrocenyl chalcones 3a,b and 5 with hydrazine hydrate, phenyl hydrazine, ethyl acetoacetate, ethyl cyanoacetate and malononitrile, were also studied. Possible reaction mechanisms were discussed and structures of the new products were unambiguously characterized by common analytical and spectroscopic methods.

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