Mutual Influence of (Dimethylhydrazono)methyl Groups and α-Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins

Reactions between phenylglyoxal hydrate and the N,N‐dimethylhydrazones of furfural and pyrrole‐2‐carbaldehyde run regioselectively at the 5‐position of the heterocycle. The resulting hetaryl analogues of α‐benzoins quantitatively isomerize to β‐compounds, the (dimethylhydrazono)methyl group activati...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-11, Vol.2004 (22), p.4688-4693
Main Authors: Ivonin, Sergey P., Lapandin, Andrey V., Anishchenko, Andrey A., Shtamburg, Vasilii G.
Format: Article
Language:English
Subjects:
Benzoins
Electrophilic substitution
Heterocycles
Hydrazones
Isomerization
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Summary:Reactions between phenylglyoxal hydrate and the N,N‐dimethylhydrazones of furfural and pyrrole‐2‐carbaldehyde run regioselectively at the 5‐position of the heterocycle. The resulting hetaryl analogues of α‐benzoins quantitatively isomerize to β‐compounds, the (dimethylhydrazono)methyl group activating the hetaryl residue and thus affording faster isomerization than in their unfunctionalized counterparts. The (dimethylhydrazono)methyl group is easily convertible into the aldehyde or nitrile group and can also be involved in rehydrazonation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400293