A new strategy toward fused-pyridine heterocyclic scaffolds: Bischler-Napieralski-type cyclization, followed by sulfoxide extrusion reaction.
Method development was completed for a new strategy to obtain fused-pyridine heterocyclic scaffolds. The synthetic route entails a Bischler-Napieralski-type reaction as the key step, followed by a sulfoxide extrusion reaction. The reactions of 3-amino-2-arylthiopyridines or 3-amino-4-arylthiopyridines and carboxylic acids promoted by a Lewis acid such as SnCl4 yielded novel tricyclic pyridobenzothiazepines, which could be readily converted to their corresponding oxidized products via a sequence of sulfur oxidations and eventually to benzonaphthyridines via a sulfoxide extrusion. The synthetic strategy provides an efficient way to access libraries of novel structurally diversified heterocyclic compounds with potential pharmaceutical or biological activities.
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai Street, Changchun, Jilin 130012, P. R. China.
Xianxiu
X
Xu
Sigen
S
Guo
Qun
Q
Dang
Jin
J
Chen
Xu
X
Bai
D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013454:Sulfoxides / Q000737:chemistry*
D006571:Heterocyclic Compounds; D011725:Pyridines; D013454:Sulfoxides; C023666:pyridine