1989 Fiscal Year Final Research Report Summary
Developments of New Organic Synthetic Reactions Using Inorganic Supports
| Project/Area Number |
62850148
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| Research Category |
Grant-in-Aid for Developmental Scientific Research
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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 | Faculty of Engineering, Kobe University |
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Principal Investigator |
HOJO Masaru Fac. of Eng., Kobe Univ., Dept. of Ind. Chem., Professor, 工学部, 教授 (60031043)
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| Co-Investigator(Kenkyū-buntansha) |
KAMITORI Yasuhiro Fac. of Eng., Kobe Univ., Dept. of Ind. Chem., Associate Professor, 工学部, 助教授 (10135816)
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| Project Period (FY) |
1987 – 1989
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| Keywords | Organic Synthesis Using Inorganic Supports / Substitution at Olefinic Carbons / Fluorine-Containing Heterocycles / Acylation of Aldehyde Hydrazones / Fluorine-Containing Oxadiazines / Fluorine-Containing Thiadiazines / Fluorine-Containing Naphthooxazines / Ether Exchange Reactions at Olefinic Carbon Atoms |
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| Research Abstract |
In these ten years we have been engaged in the study of development of new synthetic organic reactions with the use of silica gel as a useful catalyst. Another important recent project in our laboratory is electrophilic and nucleophilic substitution reactions at olefinic carbon atoms. The present study was undertaken to combine the both projects and to develop new synthetic methods for the syntheses of various fluorine-containing heterocycles which are otherwise difficultly accessible. The results are as follows. (1) Ethyl vinyl ether was trifluoroacetylated at the beta-position and then converted to allyl beta-trifluoroacetylvinyl ethers by reaction with various allyl alcohols in the presence of silica gel. The products were submitted to Claisen rearrangement with the use of silica gel to yield 3-allyl-1,1,1-trifluoroacetylacetones, from which various fluorine-containing heterocycles were obtained. (2) Various aldehyde hydrazones were successfully trifluoro- acetylated at the azomethine carbons and then converted by novel cyclization to fluorine- containing oxadiazines in the presence of silica gel. From these oxadiazines various fluorine-containing heterocycles such as thiadiazines, imidazoles, pyrazoles, quinoxalines, pyrazines, thiophenes, furans and pyrroles were obtained. (3) 2,4-Bistrifluoroacetyl- 1-dimethylaminonaphthalene was successfully converted with the use of silica gel as catalyst into fluorine-containing [1,2-d][1,3]oxazine.
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