Organo-catalytic synthesis of tetrahydropyridines via a domino ring opening/cyclization reaction of aziridines

A simple method for the synthesis of functionalized tetrahydropyridines via TBPAc-catalyzed domino ring opening/cyclization of aziridines with isocyanides in the presence of malononitrile has been developed with high atom economy, in which 6 - exo - dig cyclization process is observed. Tetrahydropyr...

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Bibliographic Details
Published in:Monatshefte für Chemie 2019-08, Vol.150 (8), p.1495-1501
Main Author: Samzadeh-Kermani, Alireza
Format: Article
Language:English
Subjects:
Analytical Chemistry
Catalysis
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Malononitrile
Organic Chemistry
Original Paper
Physical Chemistry
Ring opening
Substrates
Theoretical and Computational Chemistry
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Summary:A simple method for the synthesis of functionalized tetrahydropyridines via TBPAc-catalyzed domino ring opening/cyclization of aziridines with isocyanides in the presence of malononitrile has been developed with high atom economy, in which 6 - exo - dig cyclization process is observed. Tetrahydropyridines are quite remarkable owing to their multiple biological and pharmaceutical activities. This method provides rapid access to a diverse range of such compounds under mild conditions with good substrate tolerance and high efficiency. Graphic abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-019-02459-7