Selective synthesis of heterocycles and carbocycles by alkene cyclization via conjugate addition as a key reaction
Project/Area Number |
26410048
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Organic chemistry
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Research Institution | Nara University of Education |
Principal Investigator |
|
Project Period (FY) |
2014-04-01 – 2017-03-31
|
Project Status |
Completed (Fiscal Year 2016)
|
Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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Keywords | 共役付加 / ヘテロ環 / 環化反応 / ルイス酸 / エテントリカルボン酸 / 分子内環化付加 / 立体選択性 / 環化付加 / アリールプロペニルアミン / ピロリジン / 分子内[4+2]環化付加 / 三環性化合物 / 連続的反応 / シンナミルアミン / 分子内[2+2]環化付加 / シクロブタン / δ-ラクトン / ハロゲン付加環化 / ヘテロ5員環 / 触媒的環化 / 立体選択的合成 |
Outline of Final Research Achievements |
Selective synthesis of heterocycles by alkene cyclization of ethenetricarboxylates via conjugate addition has been studied. Reaction of E/Z-2-alkenyl esters and amides of ethenetricarboxylate with Lewis acids gave 2-oxotetrahydrofuran and pyrrolidine diastereomers stereospecifically. Sc(OTf)3-catalyzed cyclization of the allyl amides gave 2-oxopyrrolidine derivatives efficiently. Reaction of 2-hydrogen ethenetricarboxylate and E-cinnamylamines under the amide formation conditions led to pyrrolidine products in one pot, via intramolecular [2+2] and [4+2] cyclizations, depending on the substituents and the reaction conditions. Reaction with Z-cinnamylamines gave cis-fused tricyclic compounds via amide formation/[4+2] cyclization. The reactions with 3,3-diaryl-2-propenylamines gave cis- and trans-fused tricyclic compounds selectively, depending on the substituents, temperature and solvent. The cyclized products may be transformed to potentially useful compounds.
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Report
(4 results)
Research Products
(31 results)