Issue 38, 2018

Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

Abstract

An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37 : 63–>99 : 1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.

Graphical abstract: Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

Supplementary files

Article information

Article type
Communication
Submitted
26 Aug 2018
Accepted
12 Sep 2018
First published
13 Sep 2018

Org. Biomol. Chem., 2018,16, 6890-6894

Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

M. Xie, X. Cheng, Y. Chen, X. Wu, G. Qu and H. Guo, Org. Biomol. Chem., 2018, 16, 6890 DOI: 10.1039/C8OB02089B

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