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Quinolone analogues 1. A convenient synthesis of 1-alkyl-4-oxo-1,4-dihydropyridazino[3,4-b]quinoxaline-3-carboxylic acids

✍ Scribed by Yoshihisa Kurasawa; Akiko Tsuruoka; Nanae Rikiishi; Noriko Fujiwara; Yoshihisa Okamoto; Ho Sik Kim

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
523 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of the alkylhydrazinoquinoxaline N‐oxides 2a‐d with dimethyl acetylenedicarboxylate gave the dimethyl 1‐alkyl‐1,5‐dihydropyridazino[3,4‐b]qumoxaline‐3,4‐dicarboxylates 3a‐d, whose reaction with nitrous acid effected the C~4~‐oxidation to afford the dimethyl 1‐alkyl‐4‐hydroxy‐1,4‐dihydropyridazino‐[3,4‐b]quinoxaline‐3,4‐dicarboxylates 4a‐d, respectively. The reaction of compounds 4a‐d with 1,8‐diazabicyclo[5.4.0]‐7‐undecene in ethanol provided the ethyl 1‐alkyl‐4‐oxo‐1,4‐dihydropyridazino[3,4‐b]quinoxa‐line‐3‐carboxylates 5a‐d, while the reaction of compounds 4a‐d with potassium hydroxide furnished the 1‐alkyl‐4‐oxo‐1,4‐dihydropyridazino[3,4‐b]quinoxaline‐3‐carboxylic acids 6a‐d, respectively. Compounds 6c,d were also obtained by the reaction of compounds 5c,d with potassium hydroxide, respectively.

📜 SIMILAR VOLUMES

ChemInform Abstract: Quinolone Analogues
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Quinolone analogues 2. A facile synthesi
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Quinolone analogues 6 [1-5]. Synthesis o
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## Abstract The reaction of the quinoxaline __N__‐oxides **7a,b** with diethyl ethoxymethylenemalonate gave the 1‐methylpyridazino[3,4‐__b__]quinoxaline‐4,4‐dicarboxylates **8a,b**, whose reaction with __N__‐bromosuccinimide or __N__‐chlorosuccinimide afforded the 3‐halogeno‐1‐methylpyridazino[3,4‐

Quinolone analogues 7 [1-6]. Synthesis o
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The 3-heteroaryl-1-methylpyridazino [3,4-b]quinoxalin-4(1H)-ones 6a-e were synthesized by the oxidative-hydrolytic ring transformation of the 3-heteroaryl-1,2-diazepino[3,4-b]]quinoxaline-5-carbonitriles 9a-c, which were obtained by the 1,3-dipolar cycloaddition reaction of the 2-(2-heteroarylmethyl