Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides­: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid­ Structures

Marcelo S.  Nery; Renata P.  Ribeiro; Claudio C.  Lopes; Rosangela S. C.  Lopes

doi:10.1055/s-2003-36823

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Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid Structures

Marcelo S. Nery, Renata P. Ribeiro, Claudio C. Lopes*, Rosangela S. C. Lopes*
Universidade Federal do Rio de Janeiro, Instituto de Química, Departamento de Química Analítica, CT, , Bl. A, 5° andar, s-508, Rio de Janeiro, RJ, CEP-21949 900, Brazil
Fax: +55(21)25627854; e-Mail: iqg02022@acd.ufrj.br;

Abstract

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Abstract

A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.

Key words

carboxamides - niobium pentachloride - carboxylic acids - alkaloid - tetrahydroisoquinoline

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References

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Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides­: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid­ Structures

Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid Structures