Dataset Information


4,6-Dihydroxysalicylic Acid-Catalyzed Oxidative Condensation of Benzylic Amines and Aromatic Ketones for the Preparation of 2,4,6-Trisubstituted Pyridines and Its Application to Metal-Free Synthesis of G-Quadruplex Binding Ligands.

ABSTRACT: 4,6-Dihydroxysalicylic acid was activated under air to catalyze the one-pot oxidative condensation reaction of benzylamines with acetophenones in the presence of BF3·Et2O, affording 2,4,6-trisubstituted pyridines in yields of 59-91%. During this metal-free oxidative condensation reaction, the benzylamines not only provided the aryl moiety at the 4-position of the pyridines but also acted as the nitrogen donor. This method can be applied to the metal-free synthesis of G-quadruplex binding ligands by the sequential addition of 4-chlorobutyryl chloride and pyrrolidine to the reaction system of the 2,4,6-trisubstituted pyridine synthesis.


PROVIDER: S-EPMC6648211 | BioStudies | 2019-01-01

REPOSITORIES: biostudies

Similar Datasets

2018-01-01 | S-EPMC6644843 | BioStudies
1000-01-01 | S-EPMC4648097 | BioStudies
2013-01-01 | S-EPMC4065352 | BioStudies
2008-01-01 | S-EPMC5520577 | BioStudies
2006-01-01 | S-EPMC2538580 | BioStudies
1000-01-01 | S-EPMC6152059 | BioStudies
2014-01-01 | S-EPMC4227577 | BioStudies
2017-01-01 | S-EPMC6044853 | BioStudies
2015-01-01 | S-EPMC4569759 | BioStudies
2006-01-01 | S-EPMC2529459 | BioStudies