Development of Highly Efficient Synthetic Method Using Novel Concept "Pseudo-Intramolecular Reaction"

• Project/Area Number: 22550043
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kochi University of Technology
• Principal Investigator: NISHIWAKI Nagatoshi 高知工科大学, 工学部, 教授 (30237763)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000); Fiscal Year 2012: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000); Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 擬似分子内反応 / 高効率反応 / イミノ化反応 / ビシクロ化反応 / タンデム型反応 / ジヒドロピリジン / ケトニトリル / ピリジン / ヒドラゾン化 / ジアゼピン / ピリダジン / ニトロソ

Research Abstract

A new synthetic method was developed, in which novel concept “pseudo-intramolecular process” is used. When -nitro- -keto nitrile was allowed to react with amines, hydrazines, and diamines, polyfunctionalized 1,4-dihydropyridines, diazepines, pyridazines and bicyclic compounds were efficiently synthesized, respectively.

Research Products

• [Journal Article] The Pseudo-Intramolecular Process: A Novel Synthetic Method for Functionalized Heterocyclic Compounds (2013)
  • Author(s): Nagatoshi Nishiwaki
  • Journal Title: Heterocycles Volume: 87 Pages: 967-990
  • NAID: 120005728996
• [Journal Article] Ring Construction via Pseudo-Intramolecular Hydrazonation Using Bifunctional δ-Keto Nitrile (2012)
  • Author(s): Shotaro Hirao, Kazuya Kobiro, Jun Sawayama, Kazuhiko Saigo, and Nagatoshi Nishiwaki
  • Journal Title: Tetrahedron Letters Volume: 53 Pages: 82-85
  • NAID: 120005728992
• [Journal Article] Bicyclization Involving Pseudo-Intramolecular Imination with Diamines (2011)
  • Author(s): Nagatoshi Nishiwaki, Shotaro Hirao, Jun Sawayama, Kazuhiko Saigo, and Kazuya Kobiro
  • Journal Title: Chemical Communications Volume: 47 Pages: 4938-4940
  • NAID: 120005728986
• [Presentation] 求電子的シアノ基移動反応を利用した多官能化合物の合成 (2012)
  • Author(s): 平尾翔太郎・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応義塾大学日吉キャンパス
  • Year and Date: 2012-03-26
• [Presentation] 擬似分子内反応型アシル基交換反応に関する研究 (2012)
  • Author(s): 平井翔・平尾翔太郎・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応義塾大学日吉キャンパス
  • Year and Date: 2012-03-26
• [Presentation] Highly Efficient Transacylation via the Pseudo-Intramolecular Process (2012)
  • Author(s): Nagatoshi Nishiwaki, Sho Hirai, Shotaro Hirao, Jun Sawayama, Kazuhiko Saigo
  • Organizer: World Congress on Oleo Science & 29th ISF Congress
  • Place of Presentation: Sasebo, Japan
• [Presentation] 擬似分子内反応型アシル基交換反応に関する研究 (2012)
  • Author(s): 平井翔・平尾翔太郎・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第92 春季年会
  • Place of Presentation: 慶応義塾大学
• [Presentation] 求電子的シアノ基移動反応を利用した多官能化合物の合成 (2012)
  • Author(s): 平尾翔太郎・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第92 春季年会
  • Place of Presentation: 慶応義塾大学
• [Presentation] Highly Efficient Transacylation via the Pseudo-Intramolecular Process (2012)
  • Author(s): Nagatoshi Nishiwaki
  • Organizer: World Congress on Oleo Science & 29th ISF Congress
  • Place of Presentation: アルカス佐世保
• [Presentation] 擬似分子内イミノ化反応を鍵段階とする含窒素複素環化合物の合成 (2011)
  • Author(s): 平尾翔太郎・小廣和哉・澤山淳・西郷和彦・西脇永敏
  • Organizer: 第41回複素環化学討論会
  • Place of Presentation: 熊本市民会館
  • Year and Date: 2011-10-20
• [Presentation] Pseudo-Intramolecular Tandem Cyclization of α-Nitro-δ-keto Nitrile (2011)
  • Author(s): Shotaro Hirao, Kazuya Kobiro, Jun Sawayama, Kazuhiko Saigo, Nagatoshi Nishiwaki
  • Organizer: 23rd International Congress of Heterocyclic Chemistry (ICHC 2011)
  • Place of Presentation: Scottish Exhibition and Conference Centre, Glasgow, UK
  • Year and Date: 2011-08-01
• [Presentation] 擬似分子内イミノ化反応を経由する簡便なジアザビシクロ化合物の合成 (2011)
  • Author(s): 平尾翔太郎・小廣和哉・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-28
• [Presentation] Pseudo-Intramolecular Tandem Cyclization of α-Nitro-δ-keto Nitrile (2011)
  • Author(s): Shotaro Hirao, Kazuya Kobiro, Jun Sawayama, Kazuhiko Saigo, Nagatoshi Nishiwaki
  • Organizer: 23rd International Congress of Heterocyclic Chemistry (ICHC 2011)
  • Place of Presentation: Glasgow, UK
• [Presentation] 擬似分子内イミノ化反応を鍵段階とする含窒素複素環化合物の合成 (2011)
  • Author(s): 平尾翔太郎・小廣和哉・澤山淳・西郷和彦・西脇永敏
  • Organizer: 第41 複素環化学討論会
  • Place of Presentation: 熊本市民会館
• [Presentation] 擬似分子内イミノ化反応を経由する簡便なジアザビシクロ化合物の合成 (2011)
  • Author(s): 平尾翔太郎・小廣和哉・澤山淳・西郷和彦・西脇永敏
  • Organizer: 日本化学会第91 春季年会
  • Place of Presentation: 神奈川大学
• [Presentation] 擬似分子内反応による多官能化合物の合成 (2011)
  • Author(s): 西脇永敏・平尾翔太郎・澤山淳・西郷和彦
  • Organizer: 第98回有機合成シンポジウム
  • Place of Presentation: 早稲田国際会議場
• [Remarks]
  • URL: https://sites.google.com/site/kutnishiwakilab2/publication
• [Remarks] KUT Nishiwaki Lab Recent Publications
  • URL: https://sites.google.com/site/kutnishiwakilab2/publication
• [Remarks]
  • URL: https://sites.google.com/site/kutnishiwakilab2/research
• [Remarks]
  • URL: https://sites.google.com/site/kutnishiwakilab2/publication