Regio- and stereoselective synthesis of α-hydroxy-β-azido tetrazoles
Literature Information
Publication Date
2015-03-16
DOI
10.1039/C4QO00345D
Impact Factor
5.281
Authors
Pierre Quinodoz, Cheikh Lo, Mikhail Kletskii, Oleg Burov, Jérôme Marrot, François Couty
View Original
Abstract
Unreported α-hydroxy-β-azido tetrazoles were prepared in one step from readily available α,β-epoxy nitriles. This reaction involves a dibutyltin oxide-catalyzed cycloaddition of the nitrile reacting with TMSN3 leading to the tetrazole moiety, and opening of the epoxide by the azide anion. High levels of regio- and stereoselectivity are obtained in this reaction and are discussed, also by means of quantum mechanical DFT calculations. The azido group in these compounds could be uneventfully reduced to the corresponding amine thus leading to an α-hydroxy-β-amino tetrazole, surrogate of the corresponding carboxylic acid, while reaction with triphenylphosphine led to propargylic amines.
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Source Journal
Organic Chemistry Frontiers
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724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate
CAS Number:
1279090-25-3
Molecular Formula:
C20H30BNO5
![[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure](https://static.chemtradehub.com/structs/509/50918-26-8-4ce8.webp "[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure")
[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid
CAS Number:
50918-26-8
Molecular Formula:
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