title: Simple synthesis of some pentafluoropropenyl derivatives of pyrimidine and purine based on addition-elimination reaction.
abstract: Various pentafluoropropenyl derivatives of pyrimidine and purine bases have been obtained in good to high yield. The procedure involves the reaction of appropriate lithium derivatives prepared from both electron-rich and electron-poor pyrimidines, with the hexafluoropropene at a low temperature, via an addition-elimination process. Organolithiums of pyrimidine and purine bases give addition-elimination products as E/Z mixtures, whereas the products of the reaction of lithium amide of protected inosine with hexafluoropropene contain traces of an addition product as well as the stable perfluoroenamine. The methodology proposed allows a series of perfluorovinyl nucleobases to be obtained quickly and conveniently.
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
authors.forename: Hanna
authors.initials: H
authors.lastname: Wójtowicz-Rajchel
authors.forename: Michał
authors.initials: M
authors.lastname: Migas
authors.forename: Henryk
authors.initials: H
authors.lastname: Koroniak
mesh_terms: D015394:Molecular Structure; D011407:Propane / Q000031:analogs & derivatives* / Q000737:chemistry*; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011687:Purines; D011743:Pyrimidines; D011407:Propane