ChemInform Abstract: Secondary Amines from the Iron(II) Ion‐Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines.

Monković, Ivo; Wong, H. C.; Bachand, Carol

doi:10.1002/chin.198603117

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“…A comprehensive review by Grierson covers the scope and limitations of this reaction [48]. The Polonovski reaction is tolerant to numerous functionalities including ketones, alcohols, anilines and allylamines, which is advantageous as the use of protecting groups may be avoided during N-demethylation [49].…”

Section: Dialkyl Azodicarboxylatesmentioning

confidence: 99%

“…The initial application of this variant was the N-demethylation of the Amaryllidaceae alkaloid galanthamine (41a), via formation of the N-oxide and its subsequent treatment with FeSO 4 .7H 2 O to give N-norgalanthamine (41b) in 76% yield (Figure 13) [52]. The use of catalytic FeCl 2 .4H 2 O in a biphasic system has also demonstrated the capacity to N-demethylate a variety of tertiary amine N-oxides, including morphinan derivatives in good yields [49]. A modified non-classical Polonovski reaction has been used to N-demethylate opiates in moderate to high yields [53,54].…”

Section: Dialkyl Azodicarboxylatesmentioning

confidence: 99%

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N-Demethylation of Alkaloids

Thavaneswaran

McCamley

Scammells

2006

Natural Product Communications

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The removal of an N-methyl group, or N-demethylation, is a useful chemical transformation in organic synthesis which has particular importance in the field of alkaloid chemistry. Historically, tertiary N-methyl alkaloids have been N-demethylated using the same methods as for N-dealkylating tertiary amines. Such methodologies have included the von Braun reaction, the use of chloroformate and azodicarboxylate reagents and the Polonovski reaction, amongst others. Photochemical and biochemical procedures have also been successfully employed. This review will examine these N-demethylation procedures, with special emphasis on their application to opiate alkaloids.

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Section: Dialkyl Azodicarboxylatesmentioning

confidence: 99%