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5. Utilization of N-acyl compounds for the synthesis of tricyclic and bridged heterocyclic compounds

Author

Waly, Mohamed A. and El-Ablack, Fawzia Z.

Subjects
Article
Abstract

N-acyl derivative 4 was prepared via the reaction of methyl anthranilate with ethyl bromoacetate then refluxing the formed amino ester 3 with acetic anhydride. Cyclization of 4 in presences of sodium methoxide and methanol forming 2,4-pyrrolidindione derivative 5. 2,4-Quinolidinone 6 was obtained via cyclization of 4 in dry toluene and sodium hydride. On the other hand, indolinone derivative 8 was obtained by cyclization of 4 in toluene and free from alcohol due to retro Diekmann-condensation. On treatment of 8 with sodium hydride, refluxing toluene and in presences of Crown ether gave tricyclic compound 9. Also, treatment of 2-pyrrolidinone with trimethylene chlorobromide produced 10 which cyclized using base and solvent to the bridged ring derivatives 11. The acidic hydrolysis of 11 afforded the corresponding amino acid 13. Whereas derivative 14 was obtained by the reaction of 2-pyrrolidinone with ethyl 3-bromopropionate which on cyclization gave azabicyclo[3,2,1]octan-4,8-dione derivative 15. Compound 15 underwent acidic hydrolysis to the amino ketone derivative azepanone hydrochloride 17.

Published
2015

7. Synthesis of Some New Benzimidazole Derivatives of Pharmaceutical Interest

Author

Zakaria El-Ablack, Fawzia

Abstract

Reaction of 2-(aminomethyl)benzimidazole dihydrochloride (1) with ethyl acetoacetate was studied to give diazepinone-benzimidazole derivative (2), while, treatment of 1 with phenylhydrazono ethylacetoacetate afforded phenylhydrazino diazepinone derivative (3). On the other hand, reaction of 1 with acetyl acetone resulted in the formation of diazepine derivative (4). The reaction of 1 with ethyl cyanoacetate was studied to give 3-aminodiazepinone derivative (5). Also the reaction of 1 with acetophenone and/or benzophenone has been investigated to give the fused imidazolines 6 and 7 respectively, while the reaction of 1 with cyclopentanone gave benzimidazolyl derivative (8). Treatment of 1 with chloroacetyl chloride gave the fused pyrazinone (9). The treatment of 1 with benzoin gave the derivative (10). The structures of the hitherto unknown compounds have been confirmed from analytical and spectral data. The newly synthesized compounds were screened for antibacterial and antifungal activity.

Published
2011
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8. Michael Reaction of 3-aAryl-2,4-Dicarboethoxy-5-Hydroxy-5-Methylcyclohexanones.

Author

El-Ablack FZ, Metwally MA, and Khalil AM

Abstract

The reaction of 3-aryl-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanones 1 with benzalacetone, dibenzalacetone, benzalacetophenone, and 4-benzal-1-phenyl-3-methyl pyrazolone has been investigated to give Michael compounds 2-5 . hydrolysis of the dioxo derivative 4 afforded1,5-dicarbonyl derivative 6 which On condensation with hydrazine and/or substituted hydrazine and hydroxylamine produced1,2-diazepine and 1,2-oxazepine derivatives 7,8 respectively. Reaction of β-Keto ester 1 with 1,3-diphenylacetone afforded 9 . The structures of the hitherto unknown compounds have been confirmed by analytical and spectral data. The newly synthesized compounds have been screened to test their antimicrobial and antifungal activity.

Published
2015

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