Synthesis of Some New Heterocyclic Nitrogen Compounds Starting from Pyromellitic Dianhydride
Autor: | Ahmed M. Mosallam, Mamdouh A. Hassan, Ahmed M. Abo-Bakr, Husien. H. Temirek |
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Rok vydání: | 2012 |
Předmět: | |
Zdroj: | Oriental Journal Of Chemistry. 28:1567-1578 |
ISSN: | 2231-5039 0970-020X |
DOI: | 10.13005/ojc/280403 |
Popis: | Pyromellitic dianhydride 1 was used as starting compound for the synthesis of some new derivatives of condensed dipyrrole, dibenzoxazine, and dipyridazine. Thus, the diimide 2 was formed on fusion of 1 with urea, thiourea and/or thiosemicarbazide. Also, 1 reacted with benzylamine to give terephthalic acid derivative 3 which on fusion afforded the cyclic diimide 4. The reaction of 1 with o-aminothiophenol under different reaction conditions was investigated to give 5 in acetic acid or 6 in toluene and the later could be decarboxylated to 7. On the other hand, the action of AlCl 3 on 1 in presence of reactive aromatic substrates afforded the corresponding isomers 8a-d and 9a-d. which could be cyclized using hydroxylamine hydrochloride to give the dioxazine isomers 10a-d and 11a-d. The dioxazine isomers 10b and 11b were also obtained when 14 was allowed to react with AlCl3 in anisol. Cyclization of 8a-d and/or 9a-d using hydrazine or phenylhydrazine gives the dipyridazine isomers 13a-h and/or 14a-f respectively. |
Databáze: | OpenAIRE |
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