Chemistry and Materials Research www.
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org
ISSN 2224- 3224 (Print) ISSN 2225- 0956 (Online)
Vol 1, No.
1, 2011
8 | P a g e
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Use of 5-[2-Ethoxyquinazolone-3-yl]-2phthalimidomethylthiadiazole in the Synthesis of N- and CGlycosides via...
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Chemistry and Materials Research www.
iiste.
org
ISSN 2224- 3224 (Print) ISSN 2225- 0956 (Online)
Vol 1, No.
1, 2011
8 | P a g e
www.
iiste.
org
Use of 5-[2-Ethoxyquinazolone-3-yl]-2phthalimidomethylthiadiazole in the Synthesis of N- and CGlycosides via Amadori Rearrangement
Khalid M Darwish
Chemistry Department, Science Faculty, University of Garyounis,
Benghazi-Libya, E-mail: khaliddarwish1962@yahoo.
com
Abstract
Synthesis of novel 5-[2- aminoquinazolin-4-one-3-yl]-2- phthalimidomethylthiadiazole 2 from
5-[2-ethoxyquinazolin-4-one-3-yl]-2-phthalamidomethylthiadiazole 1.
The behavior of 2 as a
nitrogen nucleophile towards an α-hydroxy-aldehyde, such as glucose and formation of Amadori
rearrangement product (ARP) 8 that has had occurred during the course of reaction was discussed.
Keywords: N-Glycosides, α-bromoglucose, Amadori rearrangement, quinazolinone
1.
Introduction
In recent years there has been an increasing interest in the chemistry of 4(3H)-quinazolinone
derivatives becaus
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