1986 Fiscal Year Final Research Report Summary
SYNTHETIC DEVELOPMENT OF BRIDGED HETEROCYCLES
| Project/Area Number |
60470085
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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 |
有機工業化学
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| Research Institution | NAGOYA UNIVERSITY |
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Principal Investigator |
EGUCHI SHOJI Inst. of Applied Org. Chem.,Faculty of Engineering, Nagoya University, 工学部, 教授 (50023099)
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| Co-Investigator(Kenkyū-buntansha) |
OHNO MASATOMI Inst. of Applied Org. Chem., Faculty of Engineering, Nagoya University, 工学部, 助手 (50072682)
MINAMOTO KATSUMARO Inst. of Applied Org. Chem., Faculty of Engineering, Nagoya University, 工学部, 助教授 (50023106)
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| Project Period (FY) |
1985 – 1986
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| Keywords | Pericyclic reaction / Azatricyclic ring system / N-Alkenylnitrone / Cyclonucleoside / Pyranosylnucleoside / Spirothiaheterocycles / Intramolecular aza-Wittig reaction / 抗変異原性 |
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| Research Abstract |
Synthetic designs of some novel bridged heterocycles were performed in order to find any unique physical, chemical, and biological properties of these geometrically unique heterocycles, and thus, to develope new finechemicals for industrial uses. The results are summarized as follows:
1. An efficient synthetic route to several <gamma> -hydroxymonoazatricyclic ring systems has been developed utilizing the intramolecular cycloaddition of appropriate N-bicycloalkenylnitrones. Utilization of vinylidenecarbenes and azides in syntheses of nitrogen-heterocycles has been developed also.
2. Synthesis and hydrolysis studies on 2,3'-imino-bridged cyclonucleosides have explored a novel route to 2-1yxopyranosyl nucleosides. Structurally unique aspects of some long-bridged cyclonucleosides have been studied by X-ray crystallographic analysis.
3. A series of novel adamantane-2-spiro-thiaheterocycles has been prepared by thermal cycloadditions of adamantanethione with <alpha> , <beta> -unsaturated carbonyl compounds, o-quinonemethanides, 1,3-dipoles, and conjugated dienes.
4. The cyclization reactivity of several intramolecular aza-Wittig reactions as one of N-bridging methods has been clarified.
5. Some of thus obtained heterocycles have been tested for antiviral, antifungal, herbicidal, mutagenic, and antimutagenic activities. The primary results revealed an interesting antimutagenic action of adamantane-2-spiro-nathothiaheterocycle (a thiacroman derivative) against mutaions in the Ames' Salmonella microsome systems.
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