Synthesis of a new functionalized pyridoxine derivatives based on 2-halopyridine-3,4-dicarbonitriles

Two new approaches to the synthesis of functionalized pyridoxine derivatives with hydroxymethyl groups at positions 3 and 4 of the pyridine ring have been implemented based on the transformations of 2-halopyridine-3,4-dicarbonitriles. The first path involves obtaining target compounds with a halogen...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2022-01, Vol.52 (1), p.145-156
Main Authors: Fedoseev, Sergey V., Belikov, Mikhail Y., Lipin, Konstantin V., Ershov, Oleg V., Tafeenko, Victor A.
Format: Article
Language:English
Subjects:
derivatives
Furo[3,4-c]pyridin-3(1H)-one
pyridine-3,4-dicarbonitriles
pyridine-3,4-diyldimethanoles
pyridoxine derivatives
reduction
vitamin B
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two new approaches to the synthesis of functionalized pyridoxine derivatives with hydroxymethyl groups at positions 3 and 4 of the pyridine ring have been implemented based on the transformations of 2-halopyridine-3,4-dicarbonitriles. The first path involves obtaining target compounds with a halogen atom in the 2-position of pyridine by reduction of intermediate pyridine-3,4-dicarboxylates with sodium borohydride. The second approach is based on the reduction of annelated furo[3,4-c]pyridin-3(1H)-ones and allows obtaining both 2-halogen- and 2-alkylamino-substituted pyridoxine derivatives.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2021.2007403