Synthesis of pyridonoanthrapyrimidines

Autor: M. V. Kazankov, M. I. Bernadskii
Rok vydání: 1984
Předmět:
Zdroj: Chemistry of Heterocyclic Compounds. 20:808-812
ISSN: 1573-8353
0009-3122
DOI: 10.1007/bf00506977
Popis: The reaction of 6- and 8-chloroacetylaminopyrimidinoanthrones with pyridine in the case of the 8-isomer leads to the formation of a pyridone ring, while in the case of the 6-isomer it stops at the formation of the ω-pyridinium salt. The latter, like ω-pyridinium salts obtained from the 8-isomer and 1-chloroacetylaminoanthraquinone, is cyclized under the action of aniline. In this case aminopyridonoanthrapyrimidines and 1-aminoanthrapyridone are obtained. The cyclic salt, in turn, is converted to an amine, and by reductive elimination of a pyridinium group, to an unsubstituted pyridonoanthrapyrimidine. The acetylation of amines leads to the formation of an oxazole ring. Pyridonoanthrapyrimidines can also be produced from α-amino-derivatives of anthrapyridone by cyclization of dimethylformamidinium salts.
Databáze: OpenAIRE
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