Synlett 2015; 26(17): 2399-2402
DOI: 10.1055/s-0034-1379933
cluster
© Georg Thieme Verlag Stuttgart · New York

Indium-Mediated Cleavage of the Trityl Group from Protected 1H-Tetrazoles

Cherif Behloul*
a  Laboratoire des Produits Naturels d’Origine Végétale et de Synthèse Organique, Université de Constantine, Constantine 25000, Algérie   Email: afiza72@gmail.com
,
Kenza Bouchelouche
a  Laboratoire des Produits Naturels d’Origine Végétale et de Synthèse Organique, Université de Constantine, Constantine 25000, Algérie   Email: afiza72@gmail.com
,
David Guijarro
b  Departamento de Química Orgánica, Facultad de Ciencias, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain   Email: yus@ua.es
,
Francisco Foubelo
b  Departamento de Química Orgánica, Facultad de Ciencias, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain   Email: yus@ua.es
,
Carmen Nájera
b  Departamento de Química Orgánica, Facultad de Ciencias, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain   Email: yus@ua.es
,
Miguel Yus*
b  Departamento de Química Orgánica, Facultad de Ciencias, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain   Email: yus@ua.es
› Author Affiliations
Further Information

Publication History

Received: 28 January 2015

Accepted after revision: 11 May 2015

Publication Date:
19 June 2015 (eFirst)

Dedicated to the memory of Prof. Manfred Schlosser

Abstract

On treatment with indium metal in MeOH–THF, trityl groups undergo reductive removal from 1H-protected tetrazoles (including aliphatic, aromatic, and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.

Supporting Information

 
  • References and Notes


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  • 12 With the aim of trying to broaden the substrate scope, we tried to prepare some other tetrazoles functionalized with either ester or amide groups but, unfortunately, all our attempts were unsuccessful.
  • 13 Typical Procedure In a typical procedure, a mixture of 5-phenyl-1-trityl-1H-tetrazole (1a, 0.230 g, 0.5 mmol) and indium powder (0.058 g, 0.5 mmol) in MeOH (6 mL) and THF (3 mL) was stirred at 78 °C for 26 h. Then the resulting mixture was cooled to r.t., hydrolyzed with 1 M HCl (2 mL), extracted with EtOAc (3 × 10 mL), dried over anhydrous MgSO4, and evaporated (20 mbar). The resulting residue was purified by column chromatography (silica gel, hexane–EtOAc) to yield 5-phenyl-1H-tetrazole (2a, 0,134 g, 93%) as a white solid, mp 215–216 °C. 1H NMR (300 MHz, DMSO-d 6): δ = 7. 55–7.62 (m, 3 H), 8.01–8.10 (m, 2 H). 13C NMR (75 MHz, DMSO-d 6): δ = 124.1 (2 × CH), 127.0 (C), 129.4 (CH), 131.3 (2 × CH), 155.3 (C).10h
  • 14 For all detailed procedures, see the attached Supporting Information.