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Cyclocondensation reactions of heterocyclic carbonyl compounds XI . Synthesis and study of cyclocondensation reactions of some 3-substituted-5-(2-aminobenzyl)-1H-[1,2,4]triazine-6-ones

✍ Scribed by Tomáš Guckýa; Jan Slouka; Iveta Fryšová; Michal Maloň

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
569 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of 2‐substituted‐4‐(2‐nitrobenzylidene)‐4,5‐dihydrooxazol‐5‐ones (2a‐2i) was prepared by the Erlenmeyer's synthesis of 2‐nitrobenzaldehyde with acylglycines (1a‐1i) and the series of corresponding aminoderivatives (3b‐3d and 3g‐3i) was synthetised by catalytic hydrogenation of (2b‐2d and 3g‐3i). Hydrazinolysis of azlactones (2) and (3) gave hydrazides (4) and (5). The hydrazides (5) were also obtained by catalytic hydrogenation of corresponding nitroderivatives (4). The cyclization reaction of hydrazides (4) or (5) proceeded to 3,5‐disubstituted‐1,6‐dihydro‐[1,2,4]triazine‐6‐ones (6) or (7). Aminoderivatives (7) were also obtained by reduction of nitro group of compounds (6). The aminoderivatives (7) were then cyclized to 3‐substituted‐1,5‐dihydro‐[1,2,4]triazino[6,5‐b]quinolines (9), resp. its tautomers (10).

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