Reaction of Conjugated Systems Containing Nitrogen. IX. Cycloaddition Reactions of Furazan Derivatives with Anethole

Reaction of furazan derivatives with anethole (IV) was carried out with a view to establishing the structure-reactivity relationship of the 1, 4-diaza-1, 3-butadiene system. While benzofuroxan (III) reacted with IV giving 2-(p-methoxyphenyl)-3-methylquinoxaline 1, 4-dioxide (VII) through 1, 4-cycloa...

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Published inYAKUGAKU ZASSHI Vol. 93; no. 12; pp. 1643 - 1646
Main Authors SAKAMOTO, MASANORI, SHIBANO, MICHIKO, TOMIMATSU, YOSHIO
Format Journal Article
LanguageJapanese
Published Japan The Pharmaceutical Society of Japan 01.12.1973
Subjects
Alkenes
Anisoles
Cyclization
Nitrofurans
Nitrofurazone
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Summary:Reaction of furazan derivatives with anethole (IV) was carried out with a view to establishing the structure-reactivity relationship of the 1, 4-diaza-1, 3-butadiene system. While benzofuroxan (III) reacted with IV giving 2-(p-methoxyphenyl)-3-methylquinoxaline 1, 4-dioxide (VII) through 1, 4-cycloaddition with loss of hydrogen, reaction of diethyl furoxandicarboxylate (XIV) with IV, contrary to expection, gave ethyl 4-methyl-5-(p-methoxyphenyl) isoxazole-3-carboxylate (XVI). In the latter case, it was thought that the formation of XVI is probably due to thermal decomposition of XIV to nitrile oxide (XV), following the addition of IV to XV and dehydrogenation.
Bibliography:ObjectType-Article-1
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ISSN:0031-6903
1347-5231
DOI:10.1248/yakushi1947.93.12_1643