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

Autor:	Janusz Zakrzewski, Magdalena Ciechańska, Anna Makal, Anna Wrona-Piotrowicz
Rok vydání:	2018
Předmět:	Steric effects medicine.drug_class Organic Chemistry Carboxamide Alkylation medicine.disease Medicinal chemistry chemistry.chemical_compound chemistry Yield (chemistry) Amide medicine Trifluoroacetic acid Pyrene Dehydration
Zdroj:	The Journal of organic chemistry. 83(20)
ISSN:	1520-6904
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ebc69a1281af1fb00a71bf012fbee6ae https://pubmed.ncbi.nlm.nih.gov/30234301 Zobrazit plný text záznamu