Synthesis 2014; 46(15): 2065-2070
DOI: 10.1055/s-0033-1338623
paper
© Georg Thieme Verlag Stuttgart · New York

Detritylation of Protected Tetrazoles by Naphthalene-Catalyzed Lithiation

Cherif Behloul*
a  Laboratoire des Produits Naturels d’Origine Végétale et de Synthèse Organique, Université Constantine 1, Constantine 25000, Algeria   Fax: +213(31)818862   Email: afiza72@gmail.com
,
Kenza Bouchelouche
a  Laboratoire des Produits Naturels d’Origine Végétale et de Synthèse Organique, Université Constantine 1, Constantine 25000, Algeria   Fax: +213(31)818862   Email: afiza72@gmail.com
,
David Guijarro
b  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
,
Carmen Nájera
b  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
,
Miguel Yus
b  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
› Author Affiliations
Further Information

Publication History

Received: 03 March 2014

Accepted after revision: 26 March 2014

Publication Date:
30 April 2014 (eFirst)

Dedicated to the honor of Prof. Francisco Foubelo García

Abstract

Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl–tetrazole and trityl­–amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions.

Supporting Information

 
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