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Quinolone analogues 7 [1-6]. Synthesis of 3-Heteroaryl-1-methylpyridazino[3,4-b]quinoxalin-4(1H)-ones

✍ Scribed by Yoshihisa Kurasawa; Eisuke Kaji; Yoshihisa Okamoto; Ho Sik Kim

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
196 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

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-heteroarylmethylene-1methylhydrazino)quinoxaline 4-oxides with 2-chloroacrylonitrile. The assignment of the thiophene and furan ring protons was carried out through the data of the NOE, decoupling, and coupling constants.

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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 9. Synthesis of 7-me
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## Abstract magnified image The reaction of 7‐chloro‐1‐methylpyridazino[3,4‐__b__]quinoxalin‐4(1__H__)‐ones **3a‐5a** with sodium methylthiolate gave 1‐methyl‐7‐methylsulfanylpyridazino[3,4‐__b__]quinoxalin‐4(1__H__)‐ones **8a‐c**, whose reaction with __m__‐chloroperbenzoic acid afforded the 7‐met