ChemInform Abstract: A Synthesis of 1-Hydroxy-5-(2-substituted aryl)tetrazoles by Directed Lithiation

Autor:	Tom D. McCarthy, Andris J. Liepa, Dionne A. Jones, Roland H. Nearn
Rok vydání:	2001
Předmět:	Substitution reaction Chemistry Aryl Hydroxy group General Medicine Alkylation Ring (chemistry) Chloride Medicinal chemistry chemistry.chemical_compound medicine Butyllithium medicine.drug Octane
Zdroj:	ChemInform. 32
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200112139
Popis:	Dilithiation of 1-hydroxy-5-aryltetrazoles with 2 equiv. of butyllithium in the presence of N,N,N´N´-tetra-methylethylenediamine enables the introduction of ortho-substituents into the aryl ring to form compounds (6a–e). The hydroxy group of 1-hydroxy-5-phenyltetrazole may be masked by alkylation with 9-anthrylmethyl chloride. The masking group is removed with 1,4-diazabicyclo[2.2.2]octane or migrated to N 3 by treatment with trifluoro-acetic acid to form the N-oxide (10).
Databáze:	OpenAIRE
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