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

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...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 38; pp. 6890 - 6894
Main Authors Xie, Ming-Sheng, Cheng, Xuan, Chen, Yang-Guang, Wu, Xiao-Xia, Qu, Gui-Rong, Guo, Hai-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Aldehydes
Chemistry
Chemistry, Organic
Conjugation
Crystallography
Data processing
Ethers
Physical Sciences
Science & Technology
Steric hindrance
Tetrazoles
NANOPARTICLES
II RECEPTOR ANTAGONISTS
INHIBITORS
PRODRUGS
ALKYLATION
DYNAMIC KINETIC RESOLUTION
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Summary: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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02089b