title: Three-dimensional heterocycles: new uracil-based structures obtained by nucleophilic substitution at the sp2 carbon of bromoisoxazoline.
abstract: The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxaza-norborn-5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform the nucleophilic substitution of uracil anions was optimized and adapted to the steric requirements of the substrates. A library of pyrimidine derivatives was prepared in very good yields and the products were fully characterized. They are proposed as nucleoside analogues and as synthons for β-turn motifs within PNA structures.
authors: Dipartimento di Chimica, Univesità degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
authors: Misal Giuseppe
authors: MG
authors: Memeo
authors: Dipartimento di Chimica, Univesità degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
authors: Francesco
authors: F
authors: Lapolla
authors: Dipartimento di Chimica, Univesità degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
authors: Bruna
authors: B
authors: Bovio
authors: Dipartimento di Chimica, Univesità degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy. paolo.quadrelli@unipv.it.
authors: Paolo
authors: P
authors: Quadrelli
mesh_terms: D006571:Heterocyclic Compounds / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007555:Isoxazoles; D011741:Pyrimidine Nucleosides; D014498:Uracil