Synthesis of N-picolylcarboxamides in aminocarbonylation

Palladium-catalysed aminocarbonylation of iodocamphene and steroidal iodoalkenes was carried out in the presence of 2-, 3- and 4-picolylamine, as well as secondary amines possessing 1-picolyl substituent. In general, primary picolylamines require less than 2 h to achieve practically complete convers...

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Bibliographic Details
Published in:Tetrahedron 2021-05, Vol.88, p.132128, Article 132128
Main Authors: Mikle, Gábor, Bede, Fanni, Kollár, László
Format: Article
Language:English
Subjects:
Aminocarbonylation
Carboxamide
Iodoalkene
Palladium
Picolylamine
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Summary:Palladium-catalysed aminocarbonylation of iodocamphene and steroidal iodoalkenes was carried out in the presence of 2-, 3- and 4-picolylamine, as well as secondary amines possessing 1-picolyl substituent. In general, primary picolylamines require less than 2 h to achieve practically complete conversion. The secondary amines proved to be less reactive, requiring 6–24 h depending on the substrate structure. The corresponding carboxamides were isolated in moderate to excellent yields. The synthesis of α,β-unsaturated carboxamides is based on the synthesis of iodoalkene substrates from enolizable ketones. [Display omitted] •Facile synthesis of unsaturated carboxamides in palladium-catalysed aminocarbonylation.•High-yielding functionalization of camphene and steroidal skeletons.•The use of easily available, reactive iodoalkene substrates.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132128