title: Synthesis and structure of 2-pyransoylperimidines.
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.
authors.affiliation: School of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK.
authors.forename: Iain A S
authors.initials: IA
authors.lastname: Smellie
authors.forename: Andreas
authors.initials: A
authors.lastname: Fromm
authors.forename: Stephen A
authors.initials: SA
authors.lastname: Moggach
authors.forename: R Michael
authors.initials: RM
authors.lastname: Paton
mesh_terms: D018360:Crystallography, X-Ray / Q000379:methods; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006027:Glycosides; D009570:Nitriles; D011799:Quinazolines; C022049:perimidine