Synthesis and antimicrobial activities of 9H-carbazole derivatives

Nadia Salih, Jumat Salimon, Emad Yousif

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

In this work 9H-carbazole was utilized as a precursor to prepare new heterocyclic derivatives. Treatment of carbazole 1 with ethyl acetoacetate gave ethyl 9H-carbazol-9-ylacetate 2. The acetate ester derivative 2 was transformed into the 2-(9H-carbazol-9-yl)acetohydrazide 3 through treatment with hydrazine hydrate. Reaction of compound 3 with sodium nitrite/HCl afforded [(9H-carbazol-9-ylacetyl)amino]diazonium chloride 4. Compounds 3-[3-(9H-carbazol-9-ylacetyl)triazanylidene]pentane-2,4-dione 5 and ethyl 2-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-3-oxobutnoate 6 were obtained by reaction of compound 4 with acetylacetone and ethyl acetoacetate, respectively. Treatment of compounds 5 and 6 with urea and phenylhydrazine afforded 5-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-4,6-dimethyl pyrimidin-2(5H)-one 7 and 4-[3-(9H-carbazol-9-yl acetyl)triazanylidene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 8, respectively. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. All synthesized products were tested and evaluated as antimicrobial agents.

Original languageEnglish
JournalArabian Journal of Chemistry
DOIs
Publication statusAccepted/In press - 1800

Fingerprint

hydrazine
Nuclear magnetic resonance
Sodium Nitrite
Derivatives
Antimicrobial agents
Hydrazine
Anti-Infective Agents
Hydrates
Urea
Chlorides
Esters
Acetates
Sodium
Chemical analysis
ethyl acetoacetate
carbazole
acetylacetone
phenylhydrazine
phenylmethylpyrazolone
pentane

Keywords

  • 9H-Carbazole
  • Antibacterial
  • Antifungal
  • Pyrazole
  • Pyrimidine

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Synthesis and antimicrobial activities of 9H-carbazole derivatives. / Salih, Nadia; Salimon, Jumat; Yousif, Emad.

In: Arabian Journal of Chemistry, 1800.

Research output: Contribution to journalArticle

@article{39fdc4ad98574d99b1361011db2652c2,
title = "Synthesis and antimicrobial activities of 9H-carbazole derivatives",
abstract = "In this work 9H-carbazole was utilized as a precursor to prepare new heterocyclic derivatives. Treatment of carbazole 1 with ethyl acetoacetate gave ethyl 9H-carbazol-9-ylacetate 2. The acetate ester derivative 2 was transformed into the 2-(9H-carbazol-9-yl)acetohydrazide 3 through treatment with hydrazine hydrate. Reaction of compound 3 with sodium nitrite/HCl afforded [(9H-carbazol-9-ylacetyl)amino]diazonium chloride 4. Compounds 3-[3-(9H-carbazol-9-ylacetyl)triazanylidene]pentane-2,4-dione 5 and ethyl 2-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-3-oxobutnoate 6 were obtained by reaction of compound 4 with acetylacetone and ethyl acetoacetate, respectively. Treatment of compounds 5 and 6 with urea and phenylhydrazine afforded 5-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-4,6-dimethyl pyrimidin-2(5H)-one 7 and 4-[3-(9H-carbazol-9-yl acetyl)triazanylidene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 8, respectively. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. All synthesized products were tested and evaluated as antimicrobial agents.",
keywords = "9H-Carbazole, Antibacterial, Antifungal, Pyrazole, Pyrimidine",
author = "Nadia Salih and Jumat Salimon and Emad Yousif",
year = "1800",
doi = "10.1016/j.arabjc.2011.08.013",
language = "English",
journal = "Arabian Journal of Chemistry",
issn = "1878-5352",
publisher = "King Saud University",

}

TY - JOUR

T1 - Synthesis and antimicrobial activities of 9H-carbazole derivatives

AU - Salih, Nadia

AU - Salimon, Jumat

AU - Yousif, Emad

PY - 1800

Y1 - 1800

N2 - In this work 9H-carbazole was utilized as a precursor to prepare new heterocyclic derivatives. Treatment of carbazole 1 with ethyl acetoacetate gave ethyl 9H-carbazol-9-ylacetate 2. The acetate ester derivative 2 was transformed into the 2-(9H-carbazol-9-yl)acetohydrazide 3 through treatment with hydrazine hydrate. Reaction of compound 3 with sodium nitrite/HCl afforded [(9H-carbazol-9-ylacetyl)amino]diazonium chloride 4. Compounds 3-[3-(9H-carbazol-9-ylacetyl)triazanylidene]pentane-2,4-dione 5 and ethyl 2-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-3-oxobutnoate 6 were obtained by reaction of compound 4 with acetylacetone and ethyl acetoacetate, respectively. Treatment of compounds 5 and 6 with urea and phenylhydrazine afforded 5-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-4,6-dimethyl pyrimidin-2(5H)-one 7 and 4-[3-(9H-carbazol-9-yl acetyl)triazanylidene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 8, respectively. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. All synthesized products were tested and evaluated as antimicrobial agents.

AB - In this work 9H-carbazole was utilized as a precursor to prepare new heterocyclic derivatives. Treatment of carbazole 1 with ethyl acetoacetate gave ethyl 9H-carbazol-9-ylacetate 2. The acetate ester derivative 2 was transformed into the 2-(9H-carbazol-9-yl)acetohydrazide 3 through treatment with hydrazine hydrate. Reaction of compound 3 with sodium nitrite/HCl afforded [(9H-carbazol-9-ylacetyl)amino]diazonium chloride 4. Compounds 3-[3-(9H-carbazol-9-ylacetyl)triazanylidene]pentane-2,4-dione 5 and ethyl 2-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-3-oxobutnoate 6 were obtained by reaction of compound 4 with acetylacetone and ethyl acetoacetate, respectively. Treatment of compounds 5 and 6 with urea and phenylhydrazine afforded 5-[3-(9H-carbazol-9-ylacetyl)triazanylidene]-4,6-dimethyl pyrimidin-2(5H)-one 7 and 4-[3-(9H-carbazol-9-yl acetyl)triazanylidene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 8, respectively. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. All synthesized products were tested and evaluated as antimicrobial agents.

KW - 9H-Carbazole

KW - Antibacterial

KW - Antifungal

KW - Pyrazole

KW - Pyrimidine

UR - http://www.scopus.com/inward/record.url?scp=80052740233&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052740233&partnerID=8YFLogxK

U2 - 10.1016/j.arabjc.2011.08.013

DO - 10.1016/j.arabjc.2011.08.013

M3 - Article

AN - SCOPUS:80052740233

JO - Arabian Journal of Chemistry

JF - Arabian Journal of Chemistry

SN - 1878-5352

ER -