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Studies on 2,3-Dioxopyrrolidines. Synthesis of Piperazine, Pyrrolo[4,5-b]indole, Pyrazino [5,6-b]indole and Arylazo Derivatives of Amino Acids

Sofan M., Fouda A., Asfah E.

Polish Journal of Chemistry

2004

Vol. 78 / nr 6

837-842

2,3-Dioxopyrrolidines 1 convert into 2,4-diketopiperazines 2 in one pot-reaction with hydrazoic acid. The pyrrolo[4,5-b]indole 6 was obtained by cyclization of p-methoxyphenylhydrazone 4 prepared via Japp-Klingemann reaction of 1a with p-methoxyphenyldiazonium chloride. Compound 5 undergoes Schmidt reaction to give the pyrazino[5,6-b]indole derivative 6. Reaction of 1b with some aryldiazonium chlorides yields arylhydrazono-_-alanines 8 and 9. Phenylhydrazonoglycine derivative 11 was synthesized via Schmidt reaction to 10 with hydrazoic acid.

1-(N,N-Dimethylamino)-2-(N-phenylcarbamoyl)-1-buten-3-one as a Building Block for the Synthesis of Heterocyclic Compounds

Elmaati T., Said S., Elenein N. A., Sofan M., Khodeir N.

Polish Journal of Chemistry

2002

Vol. 76 / nr 7

945-952

Acetoacetanilide 1 reacted withDMF-DMAto give the enaminone 2. Compound 2, when treated with hydrazines gives the pyrazoles 4a and 4b respectively, and with pyrazole derivatives 5a and 5b the pyrazolopyrimidines 7. On the other hand, in reaction of 2 with benzimidazole and benzimidazole-2-acetonitrile, the pyrimidobenzimidazole 14 and the pyridobenzimidazole 17 were formed. 2 reacts with hippuric acid in boiling acetic anhydride to afford the pyridine 20. In the reaction of 2 with malononitrile, cyanoacetamide or malononitrile dimer compounds 21, 22 and 24 were formed. Compound 22 was further reacted with arylidenemalononitriles to give the benzopyridine derivatives 28. Pyridone 22 treated with S-DMF mixture gives thienopyridine 29, while refluxed with DMFDMA yielded the pyridopyridine 30.