Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5- b ]pyridines.

Autor: Nikol'skiy VV; N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia., Minyaev ME; N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia., Bastrakov MA; N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia., Starosotnikov AM; N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2024 May 14; Vol. 20, pp. 1069-1075. Date of Electronic Publication: 2024 May 14 (Print Publication: 2024).
DOI: 10.3762/bjoc.20.94
Abstrakt: An efficient method for the synthesis of isoxazolo[4,5- b ]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via the intramolecular nucleophilic substitution of the nitro group as a key step. The previously unknown base-promoted Boulton-Katritzky rearrangement of isoxazolo[4,5- b ]pyridine-3-carbaldehyde arylhydrazones into 3-hydroxy-2-(2-aryl[1,2,3]triazol-4-yl)pyridines was observed.
(Copyright © 2024, Nikol’skiy et al.)
Databáze: MEDLINE