Untersuchungen zum Verlauf der Cyclisierung von Alkylmalonsäure- und β-Amino-crotonsäureestern zu alkylierten Hydroxypyridincarbonsäureestern
✍ Scribed by Dr. E. Schrötter; Prof. Dr. sc. nat. H. Niedrich; Prof. Dr. sc. nat. H. Schick
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- English
- Weight
- 348 KB
- Volume
- 324
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Investigations on the Cyclization of Alkylmalonic Acid Esters with β‐Aminocrotonic Acid Esters to Alkylated Hydroxypyridine Carboxylic Acid Esters
The cyclization of substituted malonic esters with β‐aminocrotonic acid alkyl esters yields 2,4‐ or 4,6‐dihydroxy‐3‐pyridinecarboxylic acid esters, respectively, in dependence on the reaction conditions and the nature of the substituent in the malonic esters. In the presence of alcoholate malonic acid alkyl esters and alkylmalonic acid alkyl esters form 2,4‐dihydroxy‐3‐pyridinecarboxylic acid esters. Under the same conditions nitromalonic acid alkyl esters lead to 4,6‐dihydroxy‐3‐pyridinecarboxylic acid esters, which also arise in the thermal cyclization of malonic acid 2,4,6‐trichlorophenyl ester. The structure of the reaction products is determined by the relative nucleophilicity of the cyclization components.