Darstellung von 1-Cyan-4-dimethylamino-3-(pyrid-4-yl)-buta-1,3-dien-1-carbonsäure-Derivaten und ihre Cyclisierung zu 3-substituierten 2-Amino-5-(pyrid-4-yl)-pyridinen sowie den entsprechenden 1-Oxiden
✍ Scribed by Dr. V. Hagen; Dr. H.-J. Jänsch
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 428 KB
- Volume
- 332
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Synthesis of 1‐Cyano‐4‐dimethylamino‐3‐(4‐pyridinyl)‐1,3‐butadiene‐1‐carboxylic Acid Derivatives and Their Cyclisation to 3‐Substituted 2‐Amino‐5‐(4‐pyridinyl)‐pyridines Including the Corresponding 1‐Oxides
The vinylogous amidinium salt 1 is transformed to 1‐cyano‐4‐dimethylamino‐3‐(4‐pyridinyl)‐1,3‐butadiene‐1‐carboxylic acid derivatives 3a‐f by reaction with the cyanoacetic acid compounds 2a‐f in the presence of bases.
Treatment of the 3a‐f with ammonia and hydroxylamine yields the 2‐amino‐5‐(4‐pyridinyl)‐pyridine‐3‐carboxylic acid derivatives 5a‐f and the corresponding 1‐oxides 6a‐f, respectively. The products 5d, e are also prepared via the 6d, e by reduction with phosphorus trichloride.