Three-dimensional heterocycles: new uracil-based structures obtained by nucleophilic substitution at the sp2 carbon of bromoisoxazoline.
نویسندگان
چکیده
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.
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ورودعنوان ژورنال:
- Molecules
دوره 19 6 شماره
صفحات -
تاریخ انتشار 2014