Chemistry of bicyclic 5-6 systems: Synthesis of oxazolo[3,2-a]pyridines and their salts with a ring-junction nitrogen atom

Abstract

The present review highlights the synthetic procedures reported for the preparation of oxazolo[3,2-a]pyridines as a class of 5-6 bicyclic heterocycles with a nitrogen atom at the ring junction. The different sections included the synthesis of the investigated analogs through the reactions of (1) β-ketoesters with α,β-unsaturated ketones (2) δ-oxoacids or esters or unsaturated carboxylic acids with glycinol derivatives (3) unsaturated ketoesters with enamines (4) ethoxymethylenes with amidoglycinol derivatives (5) pyridinium salts with phenylglycinol (6) Multicomponent reactions, and (7) Synthesis of tetracyclic systems. The aim of the present study is to demonstrate a synopsis of the synthesis of compounds containing oxazolo[3,2-a]pyridine skeleton with high yields using readily and accessible starting materials, and efficient synthetic routes until now. The stereochemistry of the obtained enantiopure heterocycles, the isolation of the isomers and the reaction mechanisms of the unexpected products are discussed.

GRAPHICAL ABSTRACT

The present review demonstrates a synopsis of the synthesis of compounds containing oxazolo[3,2-α]pyridine skeleton with high yields using readily and accessible starting materials, and efficient synthetic routes up till now.

KEYWORDS:

• Fused heterocycles
• mechanistic routes
• oxazolo[3,2-a]pyridine
• synthetic applications
• synthetic routes