ChemInform Abstract: Chemoselective N-Alkylation of 2-Hydroxycarbazole as a Model for the Synthesis of N-Substituted Pyrrole Derivatives Containing Acidic Functions

Autor:	Giovanni Spanò, Artan Trebicka, Dario Landini, Domenico Albanese, Michele Penso
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Solvent chemistry.chemical_compound chemistry Hydride Anhydrous Halide Diglyme General Medicine Alkylation 2-hydroxycarbazole Medicinal chemistry Alkyl
Zdroj:	ChemInform. 26
ISSN:	0931-7597
DOI:	10.1002/chin.199539149
Popis:	2-Hydroxycarbazole ( 1 ) was chemoselectively N -alkylated with several alkyl halides 3 by generating the corresponding N , O -dianion using excess sodium hydride in a suitable solvent, under anhydrous conditions. The highest yields (87–96%) of 9-alkyl-2-hydroxycarbazoles 4 and the mildest reaction conditions were reached in THF containing DMF as an additive (2 mol equiv), but other solvents (DMSO, diglyme, DME) or solvent-additive systems (THF-diglyme, THF-DMSO, DME-DMF, diglyme-DMF) are effective.
Databáze:	OpenAIRE
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