Sophisticated utilization of oximes in construction of nitrogen-containing carbon-frameworks
| Project/Area Number |
25460022
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Showa Pharmaceutical University |
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Principal Investigator |
TAMURA Osamu 昭和薬科大学, 薬学部, 教授 (30257141)
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | O-シリルオキシム / N-アシルニトロン / チイルラジカル / アルキニルO-シリルオキシム / ラジカル環化 / N-ボラノニトロン / 付加環化 / ω-アルケニルオキシム / N-アシル化 / S-アルコキシカルボニル-２－メルカプトピリジン / N-選択的 / 保護基導入剤 / オキシム / ニトロン / アシル化 / 分子内付加環化 / 分子内付加環化反応 |
|---|
| Outline of Final Research Achievements |
(1) Omega-alkenyl oximes, on heating with Boc2O, underwent N-acylation leading to N-Boc nitrones, which caused intramolecular cycloaddition. Acylating reagent that is more adequate for the present cycloaddition was also explored. (2) A C-amide-substituted O-silylated oxime, on treatment with BF3-OEt2, in situ generated boracyclic nitrone-type intermediate, which underwent cycloaddition with alkenes to give 3,5-cis-isoxazolidines as the major products. (3) ω-Alkynyl O-tert-butyldiphenyl- silyloximes, on treatment with odorless 4-tert-butylbenzenethiol in the presence of AIBN in boiling benzene, underwent addition of thiyl radical followed by radical cyclization of the corresponding vinyl radicals onto the O-silyloxime moieties to give cyclic O-silylhydroxylamines in good yields.
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Report
(4 results)
Research Products
(34 results)
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[Book] Methods and Applications of Cycloaddition Reactions in Organic Syntheses2014
Author(s)
A. Kamimura，S. Minakata, A. D. Smith, K. Takasu, M. Abe, O. Tamura, H. Suga, F. Machetti, N. Nishiwaki, S. D. R. Christie, Y. Ukaji, R. P. Hsung, A. Padwa, C. Kitamura, H. Uno, S. E. Denmark, Z.-X. Yu, P. Chiu, M. Harmata, H. Pellissier
Total Pages
672
Publisher
John Wiley & Sons, Inc
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