Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C)

• Authors: Leonor Méndez , Vladimir Kouznetsov
• Languages of publication: EN

Abstracts

EN

We report an efficient and useful synthesis of new attractive spiropiperdine scaffolds 4 based on an intramolecular acyl transfer process in 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 3 using simple and mild debenzylation reaction conditions (HCOONH4/Pd/C). The compounds 3 were prepared by acylating 1-benzyl-4′-methyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 2 that are easily available from 1-benzyl-4-piperidone 1. The intramolecular character of this process was proven primarily through a crossover experiment technique. Through an examination of all spectroscopic information (1H, 13C NMR, VT-1H NMR, and 2D NMR) it was possible to correctly predict amide configurations and piperidine ring conformations of starting and final spiropiperidine compounds. [...]

Keywords

EN

Spiropiperidines; 1′-Acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines]; Intramolecular acyl transfer process; Debenzylation reaction

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 5
• Pages: 877-885

Dates

published

1 - 10 - 2011

online

24 - 7 - 2011

Contributors

author

Leonor Méndez

• Environmental Research Group, Environmental Chemistry Faculty, Santo Tomas University, A.A. 1076, Bucaramamga, Colombia

author

Vladimir Kouznetsov

• Laboratory of Organic & Biomolecular Chemistry, School of Chemistry, Industrial University of Santander, A.A. 678, Bucaramamga, Colombia

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Identifiers

DOI

10.2478/s11532-011-0082-y