Syntheses of 1,2,4-oxadiazoles from bis-dialkynic ketones and syntheses of 6,7-dihydrofuro[3,4-c]pyridines and 3,4-diaryloylpyridines from N-homopropargylic β-enaminones

Date

2025-8

Author

Yılmaz, Elif Serel

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1,2,4- Oxadiazoles have been intensely studied in recent decades as an important class of heterocycles, and they continue to attract great attention due to their growing significance in both bioactive compounds and materials science. Pyridines represent another widely studied class of heterocycles, notable for their extensive presence in the structures of pharmaceuticals, vitamins, food flavorings, dyes, adhesives, insecticides, and herbicides. In this thesis, we report the one-pot synthesis of novel symmetrical 1,2,4-oxadiazoles through a KOH-mediated reaction of amidoximes with bis-dialkynic ketones. After reaction optimization, a total of 10 novel 1,2,4-oxadiazole derivatives were synthesized in moderate to good yields. In the second part of the thesis, we discovered a novel reaction of Nhomopropargylic β-enaminones with molecular iodine and/or N-iodosuccinimide, leading to the formation of 6,7-dihydrofuro[3,4-c]pyridines and/or 3,4diaryloylpyridines. When reacted with excess molecular iodine or Niodosuccinimide in the presence of cesium carbonate, N-homopropargylic βenaminones afforded 6,7-dihydrofuro[3,4-c]pyridine derivatives. In some cases, the reaction also produced 3,4-diaryloylpyridines, involving the generation of a new carbonyl (ketone) group. Overall, the synthesis of 16 novel 6,7-dihydrofuro[3,4c]pyridine derivatives were achieved in moderate yields. Additionally, 9 novel 3,4diaryloylpyridine derivatives were isolated from the same reaction in moderate yields.

Subject Keywords

Pyridines, dihydrofuropyridines, 1,2,4-Oxadiazoles, cyclization, N-homopropargylic β-enaminones

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https://hdl.handle.net/11511/115574

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Graduate School of Natural and Applied Sciences, Thesis