A Simple and Efficient Synthesis of New Dihydrospiro[(1H)Quinoline-2,1′-Cyclohexane] Derivatives Via Internal Friedel-Crafts Alkene Alkylation of N-(1-Allylcyclohexanyl)Ethylphenylamine

New substituted dihydrospiro[(1H)quinoline-2,1′-cyclohexanes] were prepared by the internal alkene alkylation of N-(1-allylcyclohexanyl) ethylphenylamine obtained from the corresponding ketimine and allylmagnesium bromide. The 1-allyl-6-ethyl-4-methyl-3,4-dihydrospiro[(1H)quinoline-2,1′-cyclohexane]...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2005-03, Vol.35 (4), p.621-629
Main Authors: Kouznetsov, Vladímir V., Duarte, Luz Dary Avellaneda, Stashenko, Elena E.
Format: Article
Language:English
Subjects:
amino-Claisen transposition
Internal alkene Friedel-Crafts alkylation
spiroquinolines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New substituted dihydrospiro[(1H)quinoline-2,1′-cyclohexanes] were prepared by the internal alkene alkylation of N-(1-allylcyclohexanyl) ethylphenylamine obtained from the corresponding ketimine and allylmagnesium bromide. The 1-allyl-6-ethyl-4-methyl-3,4-dihydrospiro[(1H)quinoline-2,1′-cyclohexane] undergoes an amino-Claisen transposition (BF 3  · Et 2 O) to afford the 8-allyl-6-ethyl-4-methyl substituted spiroquinolines or a second internal alkylation reaction promoted by Brönsted acid (H 2 SO 4 ) to give a new unnatural lilolidine spiroderivative.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-200049815