Volume 29, Issue 1
Heterocyclic Compounds
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ChemInform Abstract: 1,7-Migration of Benzyl Group in 2-Substituted N-Benzylindoles.

SH. A. SAMSONIYA

SH. A. SAMSONIYA

Tbilisskii gos. univ. im. Dzhavakhishvili, Tbilisi 380028, Georgia

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I. SH. CHIKVAIDZE

I. SH. CHIKVAIDZE

Tbilisskii gos. univ. im. Dzhavakhishvili, Tbilisi 380028, Georgia

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E. O. GOGRICHIANI

E. O. GOGRICHIANI

Tbilisskii gos. univ. im. Dzhavakhishvili, Tbilisi 380028, Georgia

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N. N. MACHAIDZE

N. N. MACHAIDZE

Tbilisskii gos. univ. im. Dzhavakhishvili, Tbilisi 380028, Georgia

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Z. E. SALIYA

Z. E. SALIYA

Tbilisskii gos. univ. im. Dzhavakhishvili, Tbilisi 380028, Georgia

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First published: 24 June 2010

Abstract

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ChemInform Abstract

The reaction of ketone derivatives (I) with 1-phenyl-1-benzylhydrazine (II) gives the corresponding N-benzylindoles, which undergo subsequent debenzylation or 1,7-migration of the benzyl group in PPA above 100 °C to afford products (III) and (IV), respectively. The hydrazone intermediates [cf. (V)] as well as the N-benzylindoles [cf. (VI)] can be isolated under milder conditions.

chemical structure image

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