Details

Autor(en) / Beteiligte

• Korbad, Balaji L.
• Lee, Sang-Hyeup

Titel

Solid-Phase Approach for the Synthesis of 2-Amido-1,3,4-oxadiazoles

Ist Teil von

• Journal of heterocyclic chemistry, 2015-09, Vol.52 (5), p.1554-1558

Ort / Verlag

Hoboken: Blackwell Publishing Ltd

Erscheinungsjahr

2015

Quelle

Wiley Blackwell Single Titles

Beschreibungen/Notizen

• A new solid‐phase approach for the synthesis of 2‐amido‐1,3,4‐oxadiazoles has been developed. In this synthesis, hydroxypentyl JandaJel polymer support was treated with excess of oxalyl chloride to give resin‐bound 2‐chloro‐2‐oxoacetate, and this intermediate was then coupled with different hydrazides to give resin‐bound 2‐(N′‐acylhydrazinyl)‐2‐oxoacetate. Intramolecular dehydrative cyclization of resulting resin‐bound linear precursor followed by direct amidation using aluminum amide reagent provided 5‐substituted 1,3,4‐oxadiazoles as 2‐carboxamides. To explore the scope of this reaction sequence, we synthesized a small set of library using a combination of hydrazides and amines, and the desired products were obtained in good to high yields.