Synthesis 2014; 46(01): 49-56
DOI: 10.1055/s-0033-1340051
paper
© Georg Thieme Verlag Stuttgart · New York

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
a   Departamento 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
a   Departamento 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
a   Departamento 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*
b   UMR 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*
a   Departamento 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
› Author Affiliations
Further Information

Publication History

Received: 11 July 2013

Accepted after revision: 03 October 2013

Publication Date:
23 October 2013 (online)


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.

Supporting Information