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2004
Imidazole derivatives
R 0190
Novel Nucleophilic C—C Bond-Forming tele-Reaction of Imidazole Ring. —
first example and a possible mechanism of a C—C bond-forming nucleophilic
44- 135 The
tele-reaction of carbon nucleophiles (II) with imidazoles (I) without any activation
steps of the imidazole nucleus is presented. Depending on the substrate/sodium hydride/malonate ratio, two tele-reaction products (IV) and (V) together with a small
amount of the nucleophilic substitution product (III) are obtained. Another type of nucleophilic tele-reaction product (XII) is obtained by the reaction of (Ib) with diethyl
sodiophenylmalonate. Tele-substitution reactions also proceed by treatment of (Ib)
with organometalic reagents (VI) to give the tele-reaction products (VIII) along with
the normal SN-products (VII). — (OHTA*, S.; SATO, K.; KAWASAKI, I.;
YAMAGUCHI, Y.; NISHIO, S.; YAMASHITA, M.; J. Heterocycl. Chem. 41 (2004)
3, 335-341; Kyoto Pharm. Univ., Misasagi, Yamashina, Kyoto 607, Japan; Eng.) —
H. Hoennerscheid
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