Metal-free oxoammonium salt-mediated C(sp)-H oxidative Ugi-azide multicomponent reaction

In this work, an efficient oxidative C(sp 3 )-H Ugi-azide multicomponent reaction of cyclic benzylic amines to the corresponding α-tetrazolo compounds using a TEMPO salt as mild hydride abstractor-type oxidant is reported. This simple one-pot approach allows the direct functionalization of N-heteroc...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-04, Vol.2 (14), p.2896-298
Main Authors: Lohmann, Niklas, Milovanović, Vesna, Piekarski, Dariusz G, García Mancheño, Olga
Format: Article
Language:English
Subjects:
Additives
Amines
Azides - chemistry
Cyanides - chemistry
Metals
Molecular Structure
Oxidants
Oxidative Stress
Oxidizing agents
Room temperature
Sodium azide
Sodium azides
Substrates
Tetrazoles
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Summary:In this work, an efficient oxidative C(sp 3 )-H Ugi-azide multicomponent reaction of cyclic benzylic amines to the corresponding α-tetrazolo compounds using a TEMPO salt as mild hydride abstractor-type oxidant is reported. This simple one-pot approach allows the direct functionalization of N-heterocycles such as tetrahydroisoquinolines with a variety of isocyanides and NaN 3 as a practical azide source. The reaction proceeds at room temperature and without the need of acid additives, allowing for the use of sensitive substrates, while minimizing isocyanide polymerization to provide the desired heterocycle-tetrazole products in synthetically useful yields (up to 99%). A one-pot, oxidative Ugi-azide multicomponent reaction mediated by oxoammonium salts is presented. This method provides a direct access to α-tetrazolo N -heterocycles in excellent yields employing simple NaN 3 as azide source.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00101b