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Synthesis 2011(24): 4011-4016  
DOI: 10.1055/s-0031-1289591
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Inexpensive Phthalic Acid Promoted Domino Povarov Reaction between Anilines and N-Vinylamides: An Efficient Preparation of Privileged 4-Substituted 2-Methyl-1,2,3,4-tetrahydroquinoline Scaffolds

Vladimir V. Kouznetsov*a, Diego R. Merchan Arenasa, César J. Ortiz Areniza, Carlos M. Meléndez Gómezb
a Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
Fax: +57(76)349069; e-Mail: kouznet@uis.edu.co; e-Mail: vkuznechnik@gmail.com ;
b Grupo de Investigación en Compuestos Heterocíclicos, Departamento de Química, Facultad de Ciencias, Universidad del Atlántico, Barranquilla, Colombia
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Publikationsverlauf

Received 18 August 2011
Publikationsdatum:
08. November 2011 (online)

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Abstract

An efficient and simple synthesis of new 2-methyl-1,2,3,4-tetrahydroquinolines with C4 amide fragments based on the phthalic acid promoted domino Povarov reaction between anilines and N-vinylamides has been developed.

Key words

2-methyl-1,2,3,4-tetrahydroquinolines - acid-catalyzed Povarov reaction - domino process - phthalic acid - N-vinyl­amides

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21

After the treatment of the reaction mixture with NaHCO3 soln, the aqueous phase was treated with sat. HCl soln to recover the phthalic acid. The precipitated acid was filtered and washed with Et2O (3 × 10 mL). Finally, the phthalic acid was reused without the loss of the catalytic activity promoter giving the same results in the model reaction.