Use of 5-[2-Ethoxyquinazolone-3-yl]-2-phthalimidomethylthiadiazole in the Synthesis of N- and C-Glycosides via Amadori Rearra

Abstract

Synthesis of  novel   5-[2- aminoquinazolin-4-one-3-yl]-2- phthalimidomethylthiadiazole   2 from  5-[2-ethoxyquinazolin-4-one-3-yl]-2-phthalamidomethylthiadiazole.  The  behavior of  as a nitrogen nucleophile towards an ±-hydroxy-aldehyde,  such as glucose and formation of Amadori  rearrangement product (ARP) that has had occurred during the course of reaction was discussed.

Keywords: N-Glycosides, ±-bromoglucose,  Amadori rearrangement, quinazolinone