Development and application of novel environmental harmonized tandem reaction catalyzed by typical metal salt

• Project/Area Number: 20590027
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Hiroshima International University
• Principal Investigator: YANADA Reiko Hiroshima International University, 薬学部, 教授 (80239821)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 金属塩 / 触媒反応 / 環境調和型 / タンデム反応 / 2-アルキニルベンズアミド / 超原子価ヨウ素試薬 / ホフマン型転位 / イソシアネート / 金属塩触媒 / ホフマン転位 / 合成化学 / パラジウム / インジウム / 薗頭反応

Research Abstract

Starting from 2-alkynylbenzaldehydes and 2-alkynylanilines, In(OTf)3-catalyzed synthesis of ring-condensed heteroaromatic compounds was developed via a domino intramolecular nucleophilic attack/intermolecular cycloaddition/dehydration reaction. And a concise one-pot synthesis of indoles and isoquinolines from isocyanates which are derived from a Hofmann-type rearrangement of amides using a hypervalent iodine reagent was also developed.

Research Products

• [Journal Article] Platinum-catalyzed one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization (2010)
  • Author(s): N.Okamoto, K.Takeda, R.Yanada
  • Journal Title: J.Org.Chem. 75 Pages: 7615-7625
  • Peer Reviewed
• [Journal Article] Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T (2010)
  • Author(s): T.Abe, H.Takeda, Y.Miwa, K.Yamada, R.Yanada, M.Ishikura
  • Journal Title: Helv.Chim.Acta 93 Pages: 233-241
  • Peer Reviewed
• [Journal Article] Platinum-catalyzed synthesis of indoles and isoquinolines from 2-alkynylarylamides (2010)
  • Author(s): N.Okamoto, Y.Miwa, H.Minami, K.Takeda, R.Yanada
  • Journal Title: Synfacts Pages: 283-283
• [Journal Article] Platinum-Catalyzed One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization (2010)
  • Author(s): R.Yanada
  • Journal Title: J.Org.Chem. Volume: 75 Pages: 7615-7625
  • Peer Reviewed
• [Journal Article] Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T (2010)
  • Author(s): R.Yanada
  • Journal Title: Helv.Chim.Acta Volume: 93 Pages: 233-241
  • Peer Reviewed
• [Journal Article] One-pot tandem concise synthesis of indoles and isoquinolines from amides (2010)
  • Author(s): R.Yanada
  • Journal Title: Synfacts Pages: 283-283
• [Journal Article] Concise synthesis of (+/-)-aurantioclavine through a base-promoted Pictet-Spengler reaction (2009)
  • Author(s): K.Yamada, Y.Namerikawa, T.Haruyama, Y.Miwa, R.Yanada, M.Ishikura
  • Journal Title: Eur.J.Org.Chem. Pages: 5752-5759
  • Peer Reviewed
• [Journal Article] One-pot tandem concise synthesis of indoles and isoquinolines from amides (2009)
  • Author(s): N.Okamoto, Y.Miwa, H.Minami, K.Takeda, R.Yanada
  • Journal Title: Angew.Chem.Int.Ed. 48 Pages: 9693-9696
  • Peer Reviewed
• [Journal Article] One-pot concise syntheses of benzimidazo[2,1-a]isoquinolines by a microwave-accelerated tandem process (2009)
  • Author(s): N.Okamoto, K.Sakurai, M.Ishikura, K.Takeda, R.Yanada
  • Journal Title: Tetrahedron Lett. 50 Pages: 4167-4169
  • Peer Reviewed
• [Journal Article] Development of synthetic methods with indium (2009)
  • Author(s): R.Yanada, Y.Takemoto
  • Journal Title: J.Syn.Org.Chem.Jpn. 67 Pages: 239-47
  • NAID: 10024968086
  • Peer Reviewed
• [Journal Article] One-pot tandem concise synthesis of indoles and isoquinolines from amides (2009)
  • Author(s): R.Yanada
  • Journal Title: Angew.Chem.Int.Ed. 48 Pages: 9693-9696
  • Peer Reviewed
• [Journal Article] One-pot concise syntheses of benzimidazo[2,1-a]isoquinolines by a microwave accelerated tandem process (2009)
  • Author(s): R.Yanada
  • Journal Title: Tetrahedron Lett. 50 Pages: 4167-4169
  • Peer Reviewed
• [Journal Article] Concise synthesis of(+/-)-aurantioclavine through a base-promoted Pictet-Spengler reaction (2009)
  • Author(s): R.Yanada
  • Journal Title: Eur.J.Org.Chem. Pages: 5752-5759
  • Peer Reviewed
• [Journal Article] Development of Synthetic Methods with Indium (2009)
  • Author(s): R.Yanada
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan 67 Pages: 239-247
  • NAID: 10024968086
  • Peer Reviewed
• [Journal Article] Concise synthesis of the CDE ring system of tetrahydroisoquinoline alkaloids using carbophilic lewis acid-catalyzed hydroamidation and oxidative Friedel-Crafts cyclization (2008)
  • Author(s): S.Obika, Y.Yasui, R.Yanada, Y.Takemoto
  • Journal Title: J.Org.Chem. 73 Pages: 5206-5209
  • Peer Reviewed
• [Journal Article] Indium(III)-catalyzed tandem reactions with alkynylbenzaldehydes and alkynylanilines to heteroaromatic compounds (2008)
  • Author(s): R.Yanada, K.Hashimoto, R.Tokizane, Y.Miwa, H.Minami, K.Yanada, M.Ishikura, Y.Takemoto
  • Journal Title: J.Org.Chem. 73 Pages: 5135-5138
  • Peer Reviewed
• [Journal Article] Formal synthesis of olivacine via indolylborate (2008)
  • Author(s): M.Ishikura, N.Takahashi, K.Yamada, T.Abe, R.Yanada
  • Journal Title: Helv.Chim.Acta 91 Pages: 1828-1837
  • Peer Reviewed
• [Journal Article] Indium (III) -Catalyzed Tandem Reactions with Alkynylbenzaldehydes and Alkynylanilines to Heteroaromatic Compounds (2008)
  • Author(s): R. Yanada
  • Journal Title: J. Org. Chem. 73 Pages: 5135-5138
  • Peer Reviewed
• [Journal Article] Concise Synthesis of the CDE Ring System of Tetrahydroisoquinoline Alkaloids Using Carbophilic Lewis Acid-Catalyzed Hydroamldation and Oxidative Friedel-Crafls Cyclization (2008)
  • Author(s): R. Yanada
  • Journal Title: J. Org. Chem. 73 Pages: 5206-5209
  • Peer Reviewed
• [Journal Article] Formal Synthesis of Olivacine via Indolylborate (2008)
  • Author(s): R. Yanada
  • Journal Title: Helvetica Chimica Acta 91 Pages: 1828-1837
  • Peer Reviewed
• [Presentation] 2,3-ジヒドロキノロン類の立体選択的ワンポット合成 (2011)
  • Author(s): 岡本典子,柳田玲子
  • Organizer: 日本薬学会第131年会(31P0161)
  • Place of Presentation: 静岡
• [Presentation] 立体選択的四置換アルケンの合成とその応用 (2011)
  • Author(s): 岡本典子,保志場康人,松井奈津美,柳田玲子
  • Organizer: 日本薬学会第131年会(31P0251)
  • Place of Presentation: 静岡
• [Presentation] アルキニルベンゼンとN-ヨードスクシンイミドの反応 (2010)
  • Author(s): 柳田玲子
  • Organizer: 日本薬学会中国四国支部学術大会第49回
  • Place of Presentation: 鳥取
  • Year and Date: 2010-11-06
• [Presentation] タンデム反応を利用する機能性複素環化合物の合成 (2010)
  • Author(s): 柳田玲子
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋
  • Year and Date: 2010-11-01
• [Presentation] アミドのHofmnann型転位を利用する環状ビスインドール合成 (2010)
  • Author(s): 柳田玲子
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-28
• [Presentation] アルキニルベンゼンとN-ヨードスクシンイミドの反応 (2010)
  • Author(s): 岡本典子,坂井芳江,森田怜宇,武田敬,柳田玲子
  • Organizer: 日本薬学会中国四国支部学術大会第49回(6A14-10)
  • Place of Presentation: 鳥取
• [Presentation] タンデム反応を利用する機能性複素環化合物の合成 (2010)
  • Author(s): 岡本典子,武田敬,柳田玲子
  • Organizer: 第36回反応と合成の進歩シンポジウム(1P-50(11月1日))
  • Place of Presentation: 名古屋
• [Presentation] アミドのHofmann型転位を利用する環状ビスインドール合成 (2010)
  • Author(s): 岡本典子,武田敬,柳田玲子
  • Organizer: 日本薬学会第130年会(28P-pm460)
  • Place of Presentation: 岡山
• [Presentation] アミドの Hofmann 型転位を利用する含窒素複素環合成 (2009)
  • Author(s): 柳田玲子
  • Organizer: 第35回 反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
  • Year and Date: 2009-11-16
• [Presentation] 2-アルキニルベンズアミド誘導体のタンデム反応によるインドール合成 (2009)
  • Author(s): 柳田玲子
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-28
• [Presentation] アミドのHofmann型転位を利用する含窒素複素環合成 (2009)
  • Author(s): 岡本典子,柳田玲子,武田敬
  • Organizer: 第35回反応と合成の進歩シンポジウム(1P-28(11月16日))
  • Place of Presentation: 金沢
• [Presentation] 2-アルキニルベンズアミド誘導体のタンデム反応によるインドール合成 (2009)
  • Author(s): 岡本典子,柳田玲子,武田敬
  • Organizer: 日本薬学会第129年会(28P-am236)
  • Place of Presentation: 京都
• [Presentation] マイクロ波(MW)を利用したタンデム環化反応 (2008)
  • Author(s): 柳田玲子
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2008-11-04
• [Presentation] 連続環化反応による複素環化合物の合成 (2008)
  • Author(s): 柳田玲子
  • Organizer: 日本薬学会第128年会
  • Place of Presentation: 横浜
  • Year and Date: 2008-03-26
• [Presentation] マイクロ波(MW)を利用したタンデム環化反応 (2008)
  • Author(s): 柳田玲子,櫻井敬輔
  • Organizer: 第34回反応と合成の進歩シンポジウム(1P-10(11月4日))
  • Place of Presentation: 京都
• [Presentation] 連続環化反応による複素環化合物の合成 (2008)
  • Author(s): 柳田玲子,櫻井敬輔
  • Organizer: 日本薬学会第128年会(26PW-pm028)
  • Place of Presentation: 横浜
• [Remarks] ホームページ等
  • URL: http://web.me.com/ph.hirokoku.u.ac.jp/OMC2/OMC.html