Ampyzine
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| Formula | C6H9N3 |
| Molar mass | 123.159 g·mol−1 |
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Ampyzine is a central nervous system stimulant.[1]
Synthesis[edit]
The classical synthetic method for constructing 2-aminopyrazines is illustrated by the synthesis of ampyzine.
The condensation between glyoxal and 2-aminomalonamide [62009-47-6] gives 3-Hydroxypyrazine-2-carboxamide [55321-99-8] (1). Acid catalyzed hydrolysis of the amide gives 3-hydroxypyrazine-2-carboxylic acid [20737-42-2] (2); oxidative decarboxylation gives 2-hydroxypyrazine [6270-63-9] (3). Halogenation with PCl5 produces 2-chloropyrazine [14508-49-7] (4). Displacement of the leaving group by dimethylamine completes the synthesis of ampyzine (5).
See also[edit]
References[edit]
- ^ Lednicer D, Mitscher LA (1980-05-13). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. ISBN 9780471043928.
- ^ Cheeseman, G. W. H. (1960). "47. The synthesis and tautomerism of some 2-substituted pyrazines". Journal of the Chemical Society (Resumed): 242. doi:10.1039/JR9600000242.
- ^ Muehlmann, Frank L. (1956). "Metabolite Analogs. V. Preparation of Some Substituted Pyrazines and Imidazo [b]pyrazines". Journal of the American Chemical Society 78 (1): 242–244. doi:10.1021/ja01582a066.
- ^ Klein, Bernard; O'Donnell, Eileen; Auerbach, Joseph (1967). "Pyrazines. V. The amination of chloropyrazines and chloropyrazine N-oxide". The Journal of Organic Chemistry. 32 (8): 2412–2416. doi:10.1021/jo01283a012.
- ^ GB1019219 idem Emele Jane Frances, Wilson B Lutz, U.S. patent 3,249,503 (1966 to Warner Lambert Pharmaceutical).
External links[edit]
Media related to Ampyzine at Wikimedia Commons
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