DEVELOPMENT OF NEW METHODOLOGIES FOR SYNTHESES OF 1,3-BIS-PYRAZOLE, 1,3-BIS-BENZO[b][1,4]DIAZEPINE AND HEXAHYDROIMIDAZO[1,2-a]PYRIDINE DERIVATIVES

Date

2025-8-14

Author

Korkmaz Yurtoğlu, Esra

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Pyrazoles are the nitrogen-containing five membered heterocycles. They possess a primary position in the design and synthesis of novel biologically active agents. In particular, bis-pyrazoles receive a gaining interest in therapeutic chemistry. Benzodiazepines are another class of heterocyclic compounds in the field of drugs and pharmaceuticals. Notably, 1,4-benzodiazepines are benefical as analgesics, muscle relaxants, sedatives and anticancer drugs. In addition, imidazo[1,2-a]pyridines are important fused heterocycles due to their presence in large number of bioactive compounds. In particular, hexahydroimidazo[1,2-a]pyridine derivatives have gained considerable attention in pharmaceutical chemistry and materials science. In this thesis, new methodologies for synthesis of 1,3-bis-pyrazoles, 1,3-bis-benzo[b][1,4]diazepines and hexahydroimidazo[1,2-a]pyridines from bis-α,β-alkynic ketones were developed. In the first part of the thesis study, a variety of bis-α,β-alkynic ketones as the starting materials have been synthesized by the reaction of 1,6-heptadiynes with aryloyl chlorides via Sonogashira cross coupling reaction. Then, their addition and cyclocondensation reactions were investigated, which provided the formation 1,3-bis-pyrazoles in the presence of benzylhydrazine dihydrochloride and 2-hydrazinopyridine. In the second part of this study, the reaction conditions were improved for the synthesis of 1,4-diazepine compounds. The conjugate addition and cyclocondensation reactions of bis-α,β-alkynic ketones with o-phenylenediamine yielded various 1,3-bis-benzo[b][1,4]diazepine derivatives. In the last part, an efficient one-pot method has been developed for the synthesis of hexahydroimidazo[1,2-a]pyridines from bis-α,β-alkynic ketones. When reacted with ethylenediamine, bis-α,β-alkynic ketones provided the formation of new 5-alkylidene-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine derivatives in moderate to good yields.

Subject Keywords

Heterocyclic compounds, bis-α,β-alkynic ketones, 1,3-bis-pyrazoles, 1,3-bis-benzo[b][1,4]diazepines, hexahydroimidazo[1,2-a]pyridines., Heterosiklik bileşikler, bis-α,β-alkinik ketonlar, 1,3-bis-pirazoller, 1,3-bis-benzo[b][1,4]diazepinler ve hekzahidroimidazo[1,2-a]piridinler.

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https://hdl.handle.net/11511/115535

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Graduate School of Natural and Applied Sciences, Thesis