1996 Fiscal Year Final Research Report Summary
Synthsis of Bioactive Heterocyclic Medium Ring Using Selective Photo-cycloaddition
| Project/Area Number |
07651063
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kagoshima University |
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Principal Investigator |
SHIMO Tetsuro Kagoshima Univ. , Fac. of Eng. , Associate Professor, 工学部, 助教授 (80041565)
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| Co-Investigator(Kenkyū-buntansha) |
UEMURA Hisako Kagoshima Univ. , Fac. of Eng. , Associate, 工学部, 助手 (20041535)
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| Project Period (FY) |
1995 – 1996
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| Keywords | Photocycloaddition / 3 (2H) -Furanone / 2-Pyrone / Cyclobutane / Frontier MO / Excited Triplet State / Medium-ring Ether / Hetero Macrocycle |
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| Research Abstract |
Photo-[2+2] cycloaddition reactions of conjugated heterocycles were investigated and the addition selectivities were analyzed by MO method. We next utilyzed some adducts for synthesis of medium-ring ethers.
1.3 (2H) -Furanone has a simple skeleton composed of cyclopentenone system. To estimate the regio-and stereoselective [2+2] photocycloaddition reactions (cyclobutane-ring formation) of the triplet furanones with alkenes, the main factors were analyzed by PM 3-CI method.
2.2-Pyrone has also a simple skeleton composed of 2,4-cyclohexadienone system. To elucidate the peri-, site- and regoselectivities of [2+2] cycloadditions of the triplet 2-pyrones with alkenes, the main factors were also analyzed.
3. Di-2-pyrones tethered by methylene chain were synthesized and the intramolecular photo-dimerization reactions were investigated. The siteselective [2+2] cycloaddition depended on the methylene chain length. Intermolecular photoreactions of di-2-pyrones with di-alkenes were also carried out to give macrocyclic compounds which have two cyclobutane rings in each products.
4. Photo-[2+2] cycloadducts of 3 (2H) - furanones with acetylenes thermally gave seven-membered ring ethers.
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