New functionalization opportunities for peri-hydroxynaphthoyl and peri-fused heterocyclic compounds

A capability was studied of hydrogenated α-pyrone heterocycle in 7-methoxy-4-(4-methoxy-phenyl)-3,4-dihydro-2 H -benzo[ h ]chromen-2-one to undergo aminolysis under the treatment with hydrazine hydrate, primary and secondary aliphatic and aromatic amines. A new approach was developed to the preparat...

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Published inRussian journal of organic chemistry Vol. 44; no. 11; pp. 1657 - 1664
Main Authors Tyurin, R. V., Zadorozhnaya, A. P., Antonov, A. N., Mezheritskii, V. V.
Format Journal Article
LanguageEnglish
Published Dordrecht SP MAIK Nauka/Interperiodica 01.11.2008
Springer Nature
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Science & Technology
Hydrazine Hydrate
Eluent Chloroform
Heteroaromatic System
Colorless Crystal
Naphtho
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Summary:A capability was studied of hydrogenated α-pyrone heterocycle in 7-methoxy-4-(4-methoxy-phenyl)-3,4-dihydro-2 H -benzo[ h ]chromen-2-one to undergo aminolysis under the treatment with hydrazine hydrate, primary and secondary aliphatic and aromatic amines. A new approach was developed to the preparation of peri hydroxyketone of naphthalene series containing a specific functional substituent in the ortho -position with respect to hydroxy group. The effect was revealed of an acetyl group in the position 9 of 7-methoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-benzo[h]chromen-2-one on the reaction of this compound with aliphatic amines and hydrazine hydrate. 9-Methoxy-1-(4-methoxyphenyl)-6-methyl-3 H -benzo[ de ]pyrido[3,2,1-if]cinnolin-3-one [9-methyl-6-methoxy-3-(4-methoxyphenyl)-10,10a-diazapyren-1-one] was obtained, a new bis- peri -fused heteroaromatic system.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428008110171