Solid-phase synthesis of trisubsituted guanidines

Autor:	Thutam P. Hopkins, Armen M. Boldi, Jeffrey M. Dener
Rok vydání:	2002
Předmět:	Nucleophilic addition General Chemistry Borane Reductive amination Chloride Guanidines Acylation chemistry.chemical_compound Solid-phase synthesis chemistry Pyridine medicine Organic chemistry Combinatorial Chemistry Techniques medicine.drug Carbodiimide
Zdroj:	Journal of combinatorial chemistry. 4(2)
ISSN:	1520-4766
Popis:	The solid-phase library synthesis of trisubstituted guanidines was accomplished. Amines were loaded onto the 4-formyl-3,5-dimethoxyphenoxymethyl linker via reductive amination. Subsequent acylation with Fmoc-4-aminomethylbenzoic acid followed by Fmoc deprotection gave solid-supported primary amines. Alternatively, sulfonylation of resin-bound secondary amines with 4-cyanobenzenesulfonyl chloride followed by borane reduction also gave solid-supported primary amines. Both resins were acylated with isocyanates to furnish solid-supported ureas. Dehydration of ureas with p-toluenesulfonyl chloride in pyridine gave solid-supported carbodiimides. Nucleophilic addition of amines to the carbodiimide bond followed by cleavage off the solid support gave trisubstituted guanidines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::91a529ec24369188e679a56d4851e209 https://pubmed.ncbi.nlm.nih.gov/11886292 Zobrazit plný text záznamu