Alkylation of the K-Region in a Sterically Hindered Pyrene Carboxamide via Directed Reaction with Alkyllithiums under Air.

Ciechanska, Magdalena; Wrona-Piotrowicz, Anna; Makal, Anna; Zakrzewski, Janusz

Ciechanska, Magdalena; Wrona-Piotrowicz, Anna; Makal, Anna; Zakrzewski, Janusz.

Afiliación

Ciechanska M; Department of Organic Chemistry, Faculty of Chemistry , University of Lódz , Tamka 12 , 91-403 Lódz , Poland.
Wrona-Piotrowicz A; Department of Organic Chemistry, Faculty of Chemistry , University of Lódz , Tamka 12 , 91-403 Lódz , Poland.
Makal A; University of Warsaw , Chemistry Department, Biological and Chemical Research Center , Zwirki i Wigury 101 , 02-089 Warszawa , Poland.
Zakrzewski J; Department of Organic Chemistry, Faculty of Chemistry , University of Lódz , Tamka 12 , 91-403 Lódz , Poland.

J Org Chem ; 83(20): 12793-12797, 2018 10 19.

Article en En | MEDLINE | ID: mdl-30234301

RESUMEN

Sterically hindered N,2,7-tri- tert-butylpyrene-1-carboxamide treated with n-BuLi, i-BuLi, s-BuLi, and n-HexLi in THF in the presence of TMEDA and air afforded trans- N,2,7-tri- tert-butylpyrene-10-alkyl-9-hydroxy-9,10-dihydropyrene-1-carboxamides in 63-74% yield. Trifluoroacetic acid promoted dehydration of these compounds gave 10-alkyl derivatives of the starting amide in 79-89% yield. The minor products of this reaction were deamidated compounds, 4-alkyl-2,7-di- tert-butylpyrenes.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Estados Unidos

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