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This section will cover the more recently reported aminopyridines. The amination products of some alkylpyridines are listed in Table V. Arylpyridines can also be aminated. For example, 2-phenylpyridine was aminated in DMA with sodium amide to give 6-amino-2-phenylpyridine in 87:/, yield (72KGS1642). The yield was a function of reaction time and temperature; prolonged heating decreased the yield, and the optimum temperature was in the range 130-140°C (73MI1). Preferential attack at the 2-position of 3-substituted pyridines is a general phenomenon in the Chichibabin reaction (64CJC1627).
Alkylpyrimidines, substituted at the 2-position with methyl, ethyl, or isopropyl groups, under the same conditions as 167, have been observed to aminate at the 4-position, despite the fact that the first step is deprotonation causing formation of anions which are strongly deactivated for further nucleophilic attack. The yield of 4amino-2-methylpyrimidine was 10%. As the acidity of the hydrogen on the 50 CHARLES K. ) KMnO, [Sec. C t2ph N NH, a-carbon atom decreased, the yields of 4-amino-2-ethyl- and 4-amino2-isopropylpyrimidine increased to 30 and 45%, respectively.
In the case of 8-methylquinoline ( 1 IS), the normal product, 2-arnino-S-methylq&oline (1 19), was obtained in 33‘><,yield and a very small amount of the abnormal product, 2-amino-3,4-dihydro-8-methylquinoline, isolated as its hydrolyzed product, 3,4-dihydro-8-methylcarbostyril(120), was obtained in 1% yield (Scheme 48) (67CPB 19 10). In a similar manner, 7-methylquinoline was treated with sodium amide to give 2-amino-3,4-dihydro-7-methylquinoline, isolated as 3,4-dihydro-7methylcarbostyril (4%).
Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown