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- W2580843564 abstract "The following thesis consists of two independent parts, both linked by a commontheme of developing new methods for the synthesis of small nitrogen containingmolecules. The first part is titled the oxidative dearomatisation of pyrrole, while thesecond part is titled the strain driven rearrangement of cyclopropenyltrichloroacetimidates.The oxidation of pyrrole typically leads to uncontrolled polymerisation anddecomposition, however it was postulated that under appropriate reaction conditionsthe controlled oxidation of pyrrole to 2-pyrrolinone would be possible. Thus, thecontrolled oxidation of electron rich pyrroles was achieved in good to excellentyields with the hypervalent iodine oxidant Dess−Martin periodinane, and also itssynthetic precursor 2-iodoxybenzoic acid (IBX). The sensitized photo-oxidation ofpyrrole was also examined by utilizing the narrow spectrum light emission fromLEDs. This led to an optimised method for the photo-oxidation of a range of pyrrolesto produce 2-pyrrolinones in good to high yields; a result that was only possible dueto limiting the absorbance of light by pyrrole and selectively exciting the dyesensitizer for the oxidation. The products from the methods of controlled pyrroleoxidation have been used in an initial study towards the total synthesis of pyrrolidinealkaloid natural products including preussin, codonopsinine and crispine A.Nitrogen-substituted benzylidene cyclopropanes were prepared by a strain-drivenOverman rearrangement of cyclopropenyl trichloroacetimidates in good to excellentyields. This methodology demonstrates the first rearrangement of a cyclopropene toan alkylidenecyclopropane with a nitrogen atom participant. The productbenzylidene cyclopropanes were used as precursors to biologically relevantcyclopropyl ureas and saturated cyclopropanes." @default.
- W2580843564 created "2017-02-03" @default.
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- W2580843564 date "2015-01-01" @default.
- W2580843564 modified "2023-09-27" @default.
- W2580843564 title "New methods for the synthesis of nitrogen containing, biologically relevant small molecules" @default.
- W2580843564 hasPublicationYear "2015" @default.
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