SYNTHESIS OF NEW AZIRIDINE DERIVATIVES AS POTENTIAL PIPERAZINE PRECURSORS

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2022-7-19

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Bayat, Duygu

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Aziridines are three-membered heterocyclic compounds. They have significant properties in organic chemistry and medicinal chemistry. Many natural products have aziridines as medicines to treat various disorders. Especially, they are essential intermediates in the synthesis of heterocyclic frameworks. Moreover, aziridines can be easily transformed into diverse types of biologically active compounds. Other remarkable heterocyclic compounds are piperazines, known as six-membered rings with two nitrogen atoms at 1,4-position in the structure. Similarly, critical pharmacological compounds, especially some antibiotics, contain piperazine structures. Aziridine-fused piperazine precursors are rare compounds due to their extremely high ring strain. They have tremendous potential to be active biological compounds. In addition to that, aziridine-fused piperazine precursors can be easily converted to functionalized piperazine structures. However, the characterizable and isolable ones are limited in the literature. In this study, different aziridines were obtained by using the Gabriel-Cromwell strategy. Starting with aryl vinyl ketones, bromination was done first; then chiral aminoalcohol was reacted with dibromocompound to get chiral aziridines. In order to replace hydroxyl group with amino group, hydroxy group was tosylated and then reacted with azide. Reduction of azide leads to intramolecular cyclization over the ketone carbonyl. As a result of this cyclization, novel aziridine-fused piperazine imines were obtained in moderate to good yields (36-75%). This strategy can be used for the synthesis of highly functionalized piperazine derivatives.

Subject Keywords

Aziridine, Gabriel-Cromwell Reaction, piperazine precursors.

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https://hdl.handle.net/11511/98548

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

D. Bayat, “SYNTHESIS OF NEW AZIRIDINE DERIVATIVES AS POTENTIAL PIPERAZINE PRECURSORS,” M.S. - Master of Science, Middle East Technical University, 2022.