Synthesis of New Functionally Substituted Aryl- and Hetarylcarbamates Based on Ninhydrin

Autor:	A. V. Velikorodov, A. K. Chabakova, A. S. Zukhairaeva, V. B. Kovalev
Rok vydání:	2018
Předmět:	010405 organic chemistry Aryl Organic Chemistry Hydrazine 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Acetic acid chemistry.chemical_compound Phenylcarbamates Cascade reaction chemistry Ninhydrin Benzofuran Hydrate
Zdroj:	Russian Journal of Organic Chemistry. 54:1509-1514
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428018100123
Popis:	The condensation of methyl (ethyl) phenylcarbamates with ninhydrin in concentrated sulfuric acid gave dialkyl [1,3-dioxoindan-2,2-diyldi(4,1-phenylene)]biscarbamates. Treatment of the latter with hydrazine hydrate resulted in the transformation of the indandione fragment into phthalazinone. Ninhydrin reacted with methyl (hydroxyphenyl)carbamates in glacial acetic acid to produce dihydroxy derivative of oxotrihydroindeno[ 1,2-b][1]benzofuran possessing a carbamate group. Tandem reaction of ninhydrin with methyl (acetylphenyl) carbamates on heating in boiling glacial acetic acid, followed by addition of hydrazine hydrate in acetonitrile, afforded methyl (5-oxo-5H-indeno[1,2-c]pyridazin-3-yl)phenylcarbamates.
Databáze:	OpenAIRE
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