The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxazanorborn-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.
Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline
MEMEO, MISAL GIUSEPPE;BOVIO, BRUNA;QUADRELLI, PAOLO
2014-01-01
Abstract
The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxazanorborn-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
