Reaction of Epoxides. V. 1, 3-Dipolar Cycloaddition Reaction of Epoxides with Carbon-Nitrogen Double Bond Compounds

The reaction of epoxides with several conjugated C-N double bond compounds was attempted. Aromatic aldazines were found to undergo criss-cross cycloaddition toward epoxides. On the other hand, aromatic ketazines gave the oxazolidines formed by the cycloaddition of one molecule of epoxides to one of...

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Published inChemical & pharmaceutical bulletin Vol. 22; no. 7; pp. 1468 - 1476
Main Authors KOJIMA, YOKO, FURUKAWA, MITSURU, SUGITA, MAKOTO, HAYASHI, SEIGORO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1974
Japan Science and Technology Agency
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ISSN0009-2363
1347-5223
DOI10.1248/cpb.22.1468

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Summary:The reaction of epoxides with several conjugated C-N double bond compounds was attempted. Aromatic aldazines were found to undergo criss-cross cycloaddition toward epoxides. On the other hand, aromatic ketazines gave the oxazolidines formed by the cycloaddition of one molecule of epoxides to one of the C-N double bond of the ketazines. Moreover, in the reaction with N, N'-bis-benzylidene-p-phenylenediamine and N, N'-p-phenylene-bis-methylidenaniline, cycloaddition of two molecules of epoxides to two C-N double bonds of these compounds occurred to give the corresponding p-phenylenebis-oxazolidines.
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.22.1468