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Synthesis and structure of quinoxaline-substituted 1,4-dihydropyridines

✍ Scribed by G. Stumm; H.-J. Niclas; G. Winter; G. Reck

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
539 KB
Volume
324
Category
Article
ISSN
0365-6233

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✦ Synopsis

Abstract

The preparation of a novel series of quinoxaline‐substituted 1,4‐dihydropyridines is described. Thus, the reaction of 1 with acetoacetates in the presence of ammonia leads to dialkyl 2,6‐dimethyl‐4‐(quinoxaline‐1,4‐dioxid‐2‐yl)‐1,4‐dihydropyridine‐3,5‐dicarboxylates 2a‐g. Compounds 4a‐c are obtained as by‐products. The asymmetrically substituted dihydropyridines 3a‐d are prepared from 1, acetoacetates, and 3‐aminocrotonates. The desoxygenated compounds 5a,b and 6a,b are obtained by reduction with ethanol/triethylamine or Na~2~S~2~O~4~. The results of the X‐ray structure analyses of 2b and 6a are discussed.

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