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Keywords = bromonitrile oxide

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18 pages, 344 KB  
Article
Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline
by Misal Giuseppe Memeo, Francesco Lapolla, Bruna Bovio and Paolo Quadrelli
Molecules 2014, 19(6), 8661-8678; https://doi.org/10.3390/molecules19068661 - 24 Jun 2014
Cited by 4 | Viewed by 6986
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Cycloaddition Chemistry)
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