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Synthesis 2000; 2000(8): 1166-1169
DOI: 10.1055/s-2000-6326
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Studies with Functionally Substituted Heteroaromatics: The Chemistry of N-Phenylhydrazonylalkylpyridinium Salts and of Phenylhydrazonylalkylbenzoazoles

Mervat Mohammed Abdel-Khalik* , Mohammed Hilmy Elnagdi, Samia Michel Agamy
  • *Department of Chemistry, Girls College for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, A. R. of Egypt
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Publication Date:
31 December 2000 (online)

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2-Pyrid-1-yliniumacetonitrile bromide 1a and 2-pyrid-1-ylinium-1-phenylethanone bromide 1b coupled with benzenediazonium chloride to yield the corresponding phenylhydrazones 3a, b. Similarly, compounds 2a-c also coupled with aryldiazonium chloride, yielding the arylhydrazones 10a-b, which were used as precursors for the synthesis of azolypyridazinones 11a, b. Compounds 3a, b were converted into 1,2,4,5-dihydrotetrazines 4a, b on refluxing in acetonitrile in the presence of ammonium acetate. Refluxing 3a in dimethylformamide resulted in the formation of the 3-cyanoindazole 6. Compound 3a was converted to pyrazole 8 on treatment with the enaminone 7, and to hydrazonyl bromide 9 on heating in dioxane/acetonitrile. Compound 12 was synthesized from the reaction of 10b with ethanolic aqueous sodium hydroxide.

azo compounds - aryl hydrazones - coupling - heterocycles - tetrazines

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