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- W3018489849 abstract "This thesis will describe attempts to use suitably substituted 2-imidazolines in Diels-Alder reactions. In order to synthesise these target 2-imidazolines a new and reliable method for the synthesis of 2-alkyl and 2-alkenyl-2-imidazolines has been developed. Metallation at C(2a) of l-ferf-butyloxycarbonyl-2-methyl-2-imidazoline, followed by reaction with a range of electrophiles and deprotection with TFA reliably afforded N(l)- unsubstituted 2-substituted 2-imidazolines; P- or Se-electrophiles led to 2-alkenyl-2- imidazolines via Wadsworth-Emmons reaction or selenoxide elimination. In an attempt to prepare N-butadienyl-2-imidazolines via the reaction of 2-alkyl-2-imidazolines and ɑ,s-unsaturated aldehydes or ketones, tetrahydroimidazo[1,2-a]pyridines have been synthesised via conjugate addition of the heterocycle N(l) nitrogen atom followed by enamine-aldol condensation at C(2ɑ). 2-Imidazolines reacted with s-ketoesters to give tetrahydroimidazo[1,2-a]pyridin- 5-ones. Whilst examining the reactions of 2-alkyl-2-imidazolines with alkyne diesters, a new annulation was uncovered that is based on N(l) conjugate addition followed by C(2ɑ) The reaction of 2-imidazolines with dialkyl acetylenedicafboxylate afforded tetrahydropyrrolo[1,2-a]imidazole-5,6-diones. None of the 2-imidazolines synthesised that contained diene functionalities underwent either intra or intermolecular Diels-Alder reactions." @default.
- W3018489849 created "2020-05-01" @default.
- W3018489849 creator A5078393523 @default.
- W3018489849 date "2000-03-08" @default.
- W3018489849 modified "2023-09-23" @default.
- W3018489849 title "2-imidazolines in annulation studies" @default.
- W3018489849 doi "https://doi.org/10.21954/ou.ro.0000ff76" @default.
- W3018489849 hasPublicationYear "2000" @default.
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