Synthesis and structure of 2-pyransoylperimidines

Iain A S Smellie; Andreas Fromm; Stephen A Moggach; R Michael Paton

doi:10.1016/j.carres.2010.09.028

Synthesis and structure of 2-pyransoylperimidines

Carbohydr Res. 2011 Jan 3;346(1):43-9. doi: 10.1016/j.carres.2010.09.028. Epub 2010 Oct 16.

Authors

Iain A S Smellie¹, Andreas Fromm, Stephen A Moggach, R Michael Paton

Affiliation

¹ School of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK.

PMID: 21078510
DOI: 10.1016/j.carres.2010.09.028

Abstract

The first examples of 2-pyranosylperimidines are reported. The β-d-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(β-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray / methods
Glycosides / chemistry
Molecular Structure
Nitriles / chemistry
Quinazolines / chemical synthesis*
Quinazolines / chemistry

Substances

Glycosides
Nitriles
Quinazolines
perimidine