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Molecules 2014, 19(6), 8661-8678; doi:10.3390/molecules19068661
Article

Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline

, ,  and *
Dipartimento di Chimica, Univesità degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy
* Author to whom correspondence should be addressed.
Received: 7 May 2014 / Revised: 4 June 2014 / Accepted: 13 June 2014 / Published: 24 June 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
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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.
Keywords: nitrosocarbonyl intermediates; 1,3-dipolar cycloadditions; bromonitrile oxide; nucleophilic substitution at sp2 carbon; uracils; thymine; X-ray analysis; nucleosides; β-turn inducers nitrosocarbonyl intermediates; 1,3-dipolar cycloadditions; bromonitrile oxide; nucleophilic substitution at sp2 carbon; uracils; thymine; X-ray analysis; nucleosides; β-turn inducers
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Memeo, M.G.; Lapolla, F.; Bovio, B.; Quadrelli, P. Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline. Molecules 2014, 19, 8661-8678.

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