Synthesis of 2-Tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines by a One-Pot Ugi-Azide/Pictet–Spengler Process

Luis E. Cárdenas-Galindo; Alejandro Islas-Jácome; Nancy V. Alvarez-Rodríguez; Laurent El Kaim; Rocío Gámez-Montaño

doi:10.1055/s-0033-1340051

Synthesis, Table of Contents

Synthesis 2014; 46(01): 49-56
DOI: 10.1055/s-0033-1340051

paper

Synthesis of 2-Tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines by a One-Pot Ugi-Azide/Pictet–Spengler Process

Luis E. Cárdenas-Galindo

^aDepartamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México Fax: +52(473)7320006 (ext. 8168) Email: rociogm@ugto.mx

,

Alejandro Islas-Jácome

^aDepartamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México Fax: +52(473)7320006 (ext. 8168) Email: rociogm@ugto.mx

,

Nancy V. Alvarez-Rodríguez

^aDepartamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México Fax: +52(473)7320006 (ext. 8168) Email: rociogm@ugto.mx

,

Laurent El Kaim*

^bUMR 7652 (Ecole Polytechnique/ENSTA/CNRS), Laboratoire Chimie et Procédés, Ecole Nationale Supérieure des Techniques Avancées, 32 Bd Victor, 75015 Paris, France Fax: +33(1)45528322 Email: laurent.elkaim@ensta.fr

,

Rocío Gámez-Montaño*

^aDepartamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, C. P. 36050, Guanajuato, Guanajuato, México Fax: +52(473)7320006 (ext. 8168) Email: rociogm@ugto.mx

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Abstract

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Abstract

A series of novel 2-tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines were prepared in good to excellent overall yields by an efficient MW-assisted one-pot Ugi-azide/Pictet–Spengler process. This work describes the first synthesis of compounds including both 1,5-disubstituted 1H-tetrazole and 2,3,4,9-tetrahydro-1H-β-carboline heterocyclic systems.

Key words

tetrazoles - tetrahydro-1H-β-carbolines - MCR - Ugi-azide - Pictet–Spengler

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References

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