1992 Fiscal Year Final Research Report Summary
Development of one-pot synthetic method of five-membered heterocycles from olefins.
| Project/Area Number |
02554022
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | HIROSHIMA UNIVERSITY |
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Principal Investigator |
OTSUBO Tetsuo Hiroshima Univ. Fac. of Prof., 工学部, 教授 (80029884)
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| Co-Investigator(Kenkyū-buntansha) |
ASO Yoshio Hiroshima Univ. Fac. of Eng. Assit, 工学部, 助手 (60151065)
OGURA Fumio Hiroshima Univ. Fac. of Eng. Prof, 工学部, 教授 (90028150)
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| Project Period (FY) |
1990 – 1992
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| Keywords | Heterocycle / Heteroatom / Organotellurium / Addition Reaction / Cyclization Reaction |
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| Research Abstract |
This project deals with development of useful reactions using organotellurium agents such as benzenetellurinyl acetate, trifluoroacetate, and trifluoromethanesulfonate. These benzenetellurinic mixed anhydrides can behave as a nucleophile towards olefins to effect oxytellurinylation in combination with alcohol, aminotellurinylation with ethyl carbamate, and amidotellurinylation with acetonitrile. These reactions are applicable to cyclofunctionalization of olefins to cyclic ethers or amines. In addition, it has turned out that the aminotellurinylation and amidotellurinylation at a high temperature are followed by an intramolecular cyclization with elimination of the introduced phenyltellurinyl group to give 2-oxazolidinones and 2-oxazolines, respectively. A similar reaction of acetylenes gives oxazoles via an addition. This provides a convenient one-pot synthesis of five-membered heterocycles from olefins and acetylenes.
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