1988 Fiscal Year Final Research Report Summary
Development of Polyfunctionalized Pyridines Directed Toward Functional Materials
| Project/Area Number |
62470086
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
OHSHIRO Yoshiki Osaka University Faculty of Engineering Professor, 工学部, 教授 (70028984)
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| Co-Investigator(Kenkyū-buntansha) |
KOMATSU Mitsuo Osaka University Faculty of Engineering Associate Professor, 工学部, 助教授 (60029197)
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| Project Period (FY) |
1987 – 1988
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| Keywords | Functionalized pyridine / Functionalized heterocycle / ethynylation / Bicyclic pyridine / ピリジンオキシド / Reissert-Henze塩 |
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| Research Abstract |
Polyfunctionalized pyridines are very important as materials having various functions or as synthetic reagents for such materials. Thus direct introduction of ethynyl group, which undergoes various types of reactions, to pyridines and their chemical transformations were studied.
It was found that a Reissert-Henze salt generated in-situ from pyridine N-oxide and benzoyl chloride reacted with a silver acetylide to afford 2-ethynyl-pyridine. The method is applicable to a variety of substituted acetylenes and substituted pyridines including quinoline and isoquinoline. Especially the method is advantageous when pyridines having a reactive substituent such as MeCO, MeOCO, CN and, hence, many hitherto unknown polyfunctionalized pyridines could be synthesized. Regioselectivity of the reaction was also discussed.
Chemical transformations of ethynylpyridines leading to bicyclic pyridines were successful. For example, heterocycles such as quinolinol, furopyridines, and pyrrolopyridine were synthesized from 3-substituted 2-ethynyl pyridines. Furthermore, new synthetic route to indolizine derivatives was found by treating ethynylpyridine with dimethyl acetylenedicarboxylate.
As results, various synthetic routes to polyfunctionalized pyiridine derivatives were developed by utilizing ethynylated pyridines.
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