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Studies with polyfunctionally substituted heteroaromatics: New routes for the synthesis of polyfunctionally substituted pyridines and 1,2,4-triazolo[1,5-a]pyridines

✍ Scribed by Fatima Al-Omran; Mervat Mohamed Abdel Khalik; Mohamed Hilmy Elnagdi

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
631 KB
Volume
6
Category
Article
ISSN
1042-7163

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✦ Synopsis

The 1-substituted ethylidenemalononitriles la-c condensed with triethyl orthoformate in refluxing acetic anhydride to yield the dienes 2a-c. On the other hand, a mixture o f N, N-dimethylformamide and triethyl orthoformate condensed with la-d to yield the N, N-dimethylaminopentadienonitriles 2d-g. The pentadienonitriles 2d-g were also formed from the reaction of 1 a-d with dimethylformamide dimethylacetal in refluxing acetic acid. When compounds la-c were treated with dimethylformamide dimethylacetal in refluxing p-xylene, a mixture of 3,4 and 2e-g was formed.

The reaction of 2a,b with hydrazine hydrate afforded the N-amino-2-iminopyridines 5a,b. These were converted into the triazolo[l,5-a]pyridines 8a-d on treatment with benzoyl chloride and with dimethylformamide dimethylacetal. On the other hand, the reaction of2c with hydrazine hydrate afforded the pyrazolo [3,4-b]pyridine 7c. Treatment of 2a,c or 2e,g with cyanoethanoic hydrazide afforded the N-(cyanoacetamido)pvridines 9a,b. The dienes 2d,f,g afforded the pyridones 1 la-c on treatment with acetic acid and hydrochloric acid mixture. Compounds 1 1 b,c were also formed on treatment of 2b,c with acetic acid hydrochloric acid mixture. The reaction of 2d,g with ethanolic sodium ethoxide gave the ethoxypyridines 13a,b.

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