Development of novel radical building blocks specialized in the Mn(III) oxidation system and the synthesis of heterocycles

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410049
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kumamoto University
• Principal Investigator: Nishino Hiroshi 熊本大学, 自然科学研究科, 教授 (50145281)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 炭素ラジカルビルディングブロック / 多置換アセトキシジヒドロフラン類 / スピロジヒドロフラン類 / 1,2ージオキシノール類 / 環状テトラケトンビルディングブロック / スピロ化合物 / ポリキナン型複素環化合物 / インドール縮環化合物

Outline of Final Research Achievements

3-Vinyl-1,3-pentanediones and 3-cyclohexylidene-1,3-pentanediones as a new radical building block binded with conjugated side chain were newly prepared and the typical Mn(III)-based oxidative radical cyclization was investigated. As a result, when the reaction was carried out at elevated temperature under argon, poly-substituted 4-acetoxy-4,5-dihydrofurans and spirodihydrofurans such as an oxygen-heterocycles, were newly produced. While the reaction was conducted at room temperature in air, 3,6-dihydro-1,2-dioxin-3-ols and spirodihydrodioxinols were preferentially produced. Thereby,it turned out that the 1,3-dicarbonyl compounds having the conjugated side chain at the 3-position were effective as a new carbon radical building block in the Mn(III) oxidation reactions.

Free Research Field

有機化学