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Syntheses of substituted 2-(l-methyl-2-imidazolyl)quinolines

✍ Scribed by Minoo Khazan; Farzin Hadizadeh; Abbas Shafiee

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
326 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Reaction of methyllithium with 1‐methy1‐2‐imidazolecarboxaldehyde afforded the corresponding alcohol 2. Oxidation of compound 2 with manganese dioxide gave 2‐acety1‐1‐methylimidazole (3). Using compound 3 and substituted isatins 4, the corresponding quinoline‐4‐carboxylic acids (5) were prepared. The reaction of acid imidazolides of 5 with appropriate amines yielded the amides 6. Carbamic acid esters 10 were prepared by the Curtius rearrangement in good yield. Substituted quinolin‐4‐amines 13 were obtained by the acid hydrolysis of compound 10 (R~1~ = t‐Bu). Alkylation of amines 13 with diakylaminoalkyl chlorides gave compounds 14.

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