6-Magnesiated Purines: Preparation and Reaction with Aldehydes

Autor:	Dalimil Dvorak, Tomáš Tobrman
Rok vydání:	2003
Předmět:	Chemistry Organic Chemistry General Medicine Grignard reagent Ribonucleoside Biochemistry Toluene chemistry.chemical_compound Yield (chemistry) Nucleic acid Purine derivative Organic chemistry Physical and Theoretical Chemistry Purine metabolism
Zdroj:	Organic Letters. 5:4289-4291
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol0355027
Popis:	[reaction: see text] Halogen-metal exchange reaction of 9-benzyl-6-iodopurine with iPrMgCl in toluene at -80 degrees C proceeds almost quantitatively. Such a purine-derived Grignard reagent reacts selectively with aldehydes in toluene, giving the corresponding alcohols in 25-62% yield, while other functional groups such as ketones, esters, and nitriles do not react under these conditions. The reaction can be extended to protected 6-iodopurine ribonucleoside.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fc1c7fabc4348fcc14002c50175da575 https://doi.org/10.1021/ol0355027 Zobrazit plný text záznamu