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

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Received: 7 May 2014; in revised form: 4 June 2014 / Accepted: 13 June 2014 / Published: 24 June 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

Memeo MG, 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(6):8661-8678.

Chicago/Turabian Style

Memeo, Misal G.; Lapolla, Francesco; Bovio, Bruna; Quadrelli, Paolo. 2014. "Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline." Molecules 19, no. 6: 8661-8678.

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