✦ LIBER ✦

N-Azolylmethyl ketones as building blocks in heterocyclic synthesis: Synthesis of new polyfunctionally substituted azolylarylazophenols, azolylpyridones and azolylthiophenes

✍ Scribed by Balkis Al-Saleh; Morsy Ahmed El-Apasery; Mervat Mohammed Abdelkhalik; Mohammed Hilmy Elnagdi

Book ID: 102339980
Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 74 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400125

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✦ Synopsis

Abstract

The title compounds 1a‐b and 2 reacted with 2‐arylhydrazonopropanals 3a‐c to yield polyfunctionally substituted azolylarylazophenols 5 and 8. The reaction of 1b and 2 with phenylisothiocyanate in the presence of α‐haloketones afforded the azolylthiophenes 12a,b and 13a,b. The reaction of 20 with α‐haloketone afforded 5‐benzotriazol‐1‐yl‐6‐methyl‐2‐(2‐oxopropylsulfanyl)nicotinonitrile 21 that was utilized as building blocks for the synthesis of condensed pyridines. Compound 21 was condensed with dimethylformamide dimethylacetal to yield thieno[2,3‐b]pyridin‐3‐yl‐N, N‐dimethylformamidine derivative 22. This was further cyclized with sodium hydride to 1__H__‐fhieno[2,3‐b; 4,5‐b']dipyridin‐4‐one derivative 23.

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