The microwave-assisted synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition over a heterogeneous Cu-based catalyst: application to the preparation of N-13-labelled tetrazoles

The [3+2] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of a new Cu-II catalyst in N-methyl-2-pyrrolidone (NMP) to give the corresponding 5-substituted 1H-tetrazoles. The desired tetrazoles were obtained in high yields within 3-30 min by employing controll...

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Published inNew journal of chemistry Vol. 41; no. 16; pp. 8084 - 8091
Main Authors Joshi, Sameer M., Mane, Rasika B., Pulagam, Krishna R., Gomez-Vallejo, Vanessa, Llop, Jordi, Rode, Chandrashekhar
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.08.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALCOHOLS
EFFICIENT CATALYST
ACID
NITRILES
ECO-FRIENDLY SYNTHESIS
LIQUID
AZIDE
CO OXIDATION
HIGHLY EFFICIENT
AZO-COMPOUNDS
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Summary:The [3+2] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of a new Cu-II catalyst in N-methyl-2-pyrrolidone (NMP) to give the corresponding 5-substituted 1H-tetrazoles. The desired tetrazoles were obtained in high yields within 3-30 min by employing controlled microwave heating. The reaction most probably proceeds through the activation of the nitrile groups by the Cu-II species, followed by a successive [3+2] cycloaddition with the sodium azide. The good performance of the catalyst enabled the preparation of selected tetrazoles labelled with the positron emitter nitrogen-13 even under conventional heating. The short reaction time, simple work-up procedure, and recyclability of the catalyst are advantages of the method reported here.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj00568g