Development of Catalytic Cyclization Reaction for the Construction of Oxindole Ring System

• Project/Area Number: 20750078
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: TOMOYA Miura Kyoto University, 大学院・工学研究科, 講師 (10378804)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2009: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2008: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: 合成化学 / 有機化学 / 有機工業化学 / 有機合成化学 / 触媒反応 / 環化反応 / オキシインドール / パラジウム / アリールボロン酸 / トリフルオロアセタミド / 抗癌薬 / ジボロン / ロジウム

Research Abstract

A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with various nucleophiles such as organoboronic acids, amides, alcohols, and thiols in the presence of a palladium catalyst, leading to the stereoselective formation of 3-alkylideneoxindoles.

Research Products

• [Journal Article] Development of Catalytic Reactions Triggered by Addition of Arylrhodium(I) Species across Alkynes (2010)
  • Author(s): Tomoya Miura, Masahiro Murakami
  • Journal Title: J. Syn. Org. Chem., Jpn. (in press)
  • NAID: 10026870033
  • Peer Reviewed
• [Journal Article] Synthesis of Stereodifined 3-Alkylideneoxindoles by Palladium-catalyzed Reactions of 2-(Alkynyl)aryl Isocyanoates with Thiols and Alcohols (2009)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yoshiteru Ito, Masahiro Murakami
  • Journal Title: Chem. Lett. 38 Pages: 1174-1175
  • Peer Reviewed
• [Journal Article] Stereoselective Oxindole Synthesis by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Amides (2009)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami
  • Journal Title: Org. Lett. 10 Pages: 2141-2143
  • Peer Reviewed
• [Journal Article] Stereoselective Oxindole Synthesis by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Amides (2009)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami
  • Journal Title: Organic Letters 11 Pages: 2141-2143
• [Journal Article] Synthesis of Stereodefined 3-Alkylideneoxindoles by Palladium-catalyzed Reactions of 2-(Alkynyl)aryl Isocyanates with Thiols and Alcohols (2009)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yoshiteru Ito, Masahiro Murakami
  • Journal Title: Chemistry Letters 38 Pages: 1174-1175
  • NAID: 10027175820
• [Journal Article] Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Organoboron Reagents (2008)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami
  • Journal Title: Org. Lett. 10 Pages: 4887-4889
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2- (Alkynyl) aryl Isocyanates with Organoboron Reagents (2008)
  • Author(s): Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, and Masahiro Murakami
  • Journal Title: Organic Letters 10 Pages: 4887-4889
  • Peer Reviewed
• [Journal Article] Rhodium-catalysed cyclisation reaction of allenynes with arylboronic acids (2008)
  • Author(s): Tomoya Miura
  • Journal Title: Chemical Communications Pages: 5366-5368
  • Peer Reviewed
• [Journal Article] Synthesis of Oxindoles by Palladium-Catalyzed C-H Bond Amidation (2008)
  • Author(s): Tomoya Miura, Yoshiteru Ito, and Masahiro Murakami
  • Journal Title: Chemistry Letters (in press)
  • NAID: 10025120732
• [Presentation] パラジウム触媒を用いた[1, 3]転位反応による3, 3-二置換オキシインドールの合成 (2010)
  • Author(s): 三甲野裕介・豊島武春・三浦智也・村上正浩
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] 遷移金属触媒による2-(アルキニル)アリールイソシアナートと求核剤との環化反応を利用した3-アルキリデンオキシインドールの立体選択的合成法の開発 (2009)
  • Author(s): 豊島武春・小澤治・高橋雄介・伊藤吉輝・三浦智也・村上正浩
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 同志社大学(京都)
  • Year and Date: 2009-09-10
• [Presentation] Stereoselective Synthesis of 3-Alkylideneoxindoles by Transition Metal-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Nucleophiles (2009)
  • Author(s): 〇豊島武春・小澤治・高橋雄介・伊藤吉輝・三浦智也・村上正浩
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 同志社大学(京都)
  • Year and Date: 2009-09-10
• [Presentation] パラジウム触媒による3-(シアノアルキリデン)オキシインドールの合成 (2009)
  • Author(s): 加藤治、豊島武春、三浦智也、村上正浩
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(千葉)
  • Year and Date: 2009-03-29
• [Presentation] パラジウム触媒とプロトン性求核剤を用いた2-(アルキニル)アリールイソシアナートの環化反応 (2009)
  • Author(s): 豊島武春・伊藤吉輝・三浦智也・村上 正浩
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学(千葉)
  • Year and Date: 2009-03-29
• [Presentation] パラジウム触媒による3-(シアノアルキリデン)オキシインドールの合成 (2009)
  • Author(s): 加藤治、豊島武春、三浦智也、村上正浩
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2009-03-29
• [Remarks]
  • URL: http://www.sbchem.kyoto-u.ac.jp/murakami-lab/
• [Remarks]
  • URL: http://www.sbchem.kyoto-u.ac.jp/murakami-lab/
• [Remarks]
  • URL: http://www.sbchem.kyoto-u.ac.jp/murakami-lab/