Synthesis and structure of 2-pyransoylperimidines

Iain A. S. Smellie, Andreas Fromm, Stephen A. Moggach, R. Michael Paton

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)43-49
Number of pages7
JournalCarbohydrate Research
Volume346
Issue number1
DOIs
Publication statusPublished - 3 Jan 2011
Externally publishedYes

Cite this