Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole

Autor:	Peter Uhlmann, Per Vedsø, Jakob Felding, Mikael Begtrup
Rok vydání:	1997
Předmět:	1 2 3-Triazole Organic Chemistry chemistry.chemical_element Hydrochloric acid Combinatorial chemistry Sulfur Medicinal chemistry chemistry.chemical_compound chemistry Hydrogenolysis Electrophile Halogen Benzyl group Tin
Zdroj:	The Journal of Organic Chemistry. 62:9177-9181
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo971313o
Popis:	1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.
Databáze:	OpenAIRE
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