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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 19
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Original Articles

A SIMPLE AND EFFICIENT PREPARATION OF 3,4-DIALKYLSUBSTITUTED TETRAHYDROISOQUINOLINE USING CYCLOPROPYLETHYLIDEN BENZYLAMINE

Vladimir Kouznetsov Research Center for Biomolecules, Laboratory of Fine Organic Synthesis, School of Chemistry, Industrial University of Santander, Bucaramanga, A.A. 678, ColombiaCorrespondence[email protected]
,
Alirio Palma Research Center for Biomolecules, Laboratory of Fine Organic Synthesis, School of Chemistry, Industrial University of Santander, Bucaramanga, A.A. 678, Colombia
,
Wilson Rozo Research Center for Biomolecules, Laboratory of Fine Organic Synthesis, School of Chemistry, Industrial University of Santander, Bucaramanga, A.A. 678, Colombia
,
Elena Stashenko Research Center for Biomolecules, Laboratory of Fine Organic Synthesis, School of Chemistry, Industrial University of Santander, Bucaramanga, A.A. 678, Colombia
,
Alí Bahsas Laboratorio de RMN, Grupo de Productos Naturales, Departamento de Química, Universidad de los Andes, Mérida, 5101, Venezuela
&
Juan Amaro-Luis Laboratorio de RMN, Grupo de Productos Naturales, Departamento de Química, Universidad de los Andes, Mérida, 5101, Venezuela
Pages 2965-2971 | Received 14 Sep 2001, Published online: 16 Aug 2006
 
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ABSTRACT

Intramolecular Friedel–Crafts alkylation of N-benzyl-N-(1-cyclopropylethyl)acetamide to 3,4-dialkyl substituted tetrahydroisoquinoline by reaction of the acetamide with an excess of PPA is described. The conformational study of intermediates by high resolution NMR analysis is also reported.

ACKNOWLEDGMENTS

Financial support from Colciencias (grants No. 1115-05-353-96 and 1102-05-110-97) is gratefully acknowledged.

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