Premium
Mutual Influence of (Dimethylhydrazono)methyl Groups and α‐Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins
Author(s) -
Ivonin Sergey P.,
Lapandin Andrey V.,
Anishchenko Andrey A.,
Shtamburg Vasilii G.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400293
Subject(s) - chemistry , nitrile , aldehyde , ketone , methyl ketone , methyl group , furfural , phenylglyoxal , organic chemistry , residue (chemistry) , cyclopentane , hydrate , medicinal chemistry , group (periodic table) , stereochemistry , catalysis , biochemistry , amino acid , arginine
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)