Efficient synthesis of multifunctionalyzed heterocycles using isocyanides

• Project/Area Number: 15K17820
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: Soeta Takahiro 金沢大学, 物質化学系, 准教授 (10506819)
• Project Period (FY): 2015-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
• Keywords: イソシアニド / 多成分反応 / 複素環 / 触媒的不斉反応

Outline of Final Research Achievements

Isocyanide is one of the most important building blocks in the organic chemistry because isocyanide has nucleophilicity and electrophilicity on the carbon atom. We have developed [n+1] cycloaddition reaction of isocyanide with 1,n-dipolars to afford the corresponding hetecocycles in high yields.

Research Products

• [Journal Article] 2.Development of a One-Pot Synthetic Method for Multifunctional Oxazole Derivatives Using Isocyanide Dichloride. (2017)
  • Author(s): Soeta, T.; Matsumoto, A.; Sakata, Y.; Ukaji, Y
  • Journal Title: J. Org. Chem. Volume: 82 Issue: 9 Pages: 4930-4935
  • DOI: 10.1021/acs.joc.7b00296
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines. (2017)
  • Author(s): Tong, T. M. T.; Soeta, T.; Suga, T.; Kawamoto, K.; Hayaahi, Y.; Ukaji, Y.
  • Journal Title: J. Org. Chem. Volume: 82 Pages: 1969-1976
  • NAID: 120006027761
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Palladium-catalyzed C–H Alkenylation of <i>C</i>-Aryl Nitrones (2017)
  • Author(s): Hasegawa, M.; Nomoto, A.; Suga, T.; Soeta, T.; Ukaji, Y.
  • Journal Title: Chemistry Letters Volume: 46 Issue: 1 Pages: 45-47
  • DOI: 10.1246/cl.160821
  • NAID: 130005308312
  • ISSN: 0366-7022, 1348-0715
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Effective synthesis of Benzothiophenes by [4+1] Cycloaddition of 2-Mercaptobenzaldehyde Derivatives with Isocyanides. (2016)
  • Author(s): Soeta, T.; Shitaya, S.; Okuno, T.; Fujinami, S.; Ukaji, Y.
  • Journal Title: Tetrahedron Volume: 72 Issue: 49 Pages: 7901-7905
  • DOI: 10.1016/j.tet.2016.09.054
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Palladium-Catalyzed Intermolecular Alkoxy-Alkoxycarbonylation of Vinylphenols in the Presence of Copper Salt: Unexpected Cooperative Effect of Tin Salt. (2016)
  • Author(s): Phan, N. H. T.; Furuya, T.; Soeta, T.; Ukaji, Y.
  • Journal Title: Chem. Lett. Volume: 45 Issue: 12 Pages: 1431-1433
  • DOI: 10.1246/cl.160804
  • NAID: 130005475736
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Ugi-type Multicomponent Reaction of Nitrile Imines, Isocyanides, and Isocyanates: Effective Synthesis of 1,2,4-Triazinedione Derivatives. (2016)
  • Author(s): Soeta, T.; Takashita, S.; Sakata, Y.; Ukaji, Y.
  • Journal Title: Asian J. Org. Chem. Volume: 5 Issue: 8 Pages: 1041-1047
  • DOI: 10.1002/ajoc.201600191
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] 8.Magnesium-Alkoxide Directed Photoaddition of Tetrahydrofyrans to γ,γ-Disubstituted Allylic Alcohols. (2016)
  • Author(s): Watanabe, Y.; Sakai, T.; Maeda, H.; Segi, M.; Soeta, T.; Ukaji, Y
  • Journal Title: Heterocycles Volume: 93 Issue: 2 Pages: 833-844
  • DOI: 10.3987/com-15-s(t)65
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Pre-steady-state Kinetic Studies of Redox Reactions Catalysed by Bacillus Subtilis Ferredoxin-NADP+ Oxidoreductase with NADP+/NADPH and Ferredoxin. (2016)
  • Author(s): Seo, D.; Soeta, T.; Sakurai, H.; Pierre, S.; Sakurai, T.
  • Journal Title: BBA-BIOENERGETICS Volume: 1 Pages: 309-311
  • NAID: 120005774908
  • Peer Reviewed
• [Journal Article] Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines (2016)
  • Author(s): Soeta, T.; Ishizaka, T.; Ukaji, Y.
  • Journal Title: J. Org. Chem. Volume: 81 Issue: 7 Pages: 2817-2826
  • DOI: 10.1021/acs.joc.6b00093
• [Journal Article] Phosphinic Acid-promoted Addition Reaction of Isocyanides to (Z)-Hydroximoyl Chlorides: Efficient Synthesis of α-(Hydroxyimino)amides. (2015)
  • Author(s): Soeta, T. Takashita, S.; Sakata, Y.; Ukaji, Y.
  • Journal Title: Org. Biomol.Chem. Volume: 14 Issue: 2 Pages: 694-700
  • DOI: 10.1039/c5ob02032h
  • Peer Reviewed
• [Journal Article] A One-Pot O-Sulfinative Passerini/Oxidation Reaction: Efficient Synthesis of α-(Sulfonyloxy)amide Derivatives. (2015)
  • Author(s): Soeta, T.; Matsuzaki, S.; Ukaji, Y.
  • Journal Title: J. Org. Chem Volume: 80 Issue: 7 Pages: 3688-3694
  • DOI: 10.1021/acs.joc.5b00131
  • Peer Reviewed
• [Journal Article] One-Carbon Homologation of Pyrrole Carboxaldehyde via Wittig Reaction and Mild Hydrolysis of Vinyl Ether &#8211; toward the Synthesis of a Sterically Locked Phytochrome Chromophore. (2015)
  • Author(s): Sakata, R.; Soeta, T.; Ukaji, Y.
  • Journal Title: Heterocycles Volume: 91 Pages: 593-603
  • NAID: 40020393284
  • Peer Reviewed
• [Journal Article] (Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2]-Wittig Rearrangement (2015)
  • Author(s): Kurosawa, F.; Nakano, T.; Soeta, T.; Endo, K.; Ukaji, Y.
  • Journal Title: J. Org. Chem. Volume: 80 Issue: 11 Pages: 5696-5603
  • DOI: 10.1021/acs.joc.5b00647
  • NAID: 120005647656
  • Peer Reviewed
• [Presentation] メソ位立体固定型フィトクロム発色団の開発とその光異性化の機構解明 (2017)
  • Author(s): 大橋 信彦・小林 俊晴・添田 貴宏・宇梶 裕
  • Organizer: 日本化学会 第97春季年会 (2017)
  • Place of Presentation: 慶應義塾大学 日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] ピリジン骨格を有するキラルな含窒素複素環カルベンを用いる触媒的不斉クロスベンゾイン縮合の開発 (2017)
  • Author(s): 水野 想・添田 貴宏・宇梶 裕
  • Organizer: 日本化学会 第97春季年会 (2017)
  • Place of Presentation: 慶應義塾大学 日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] α,β-不飽和ニトロンを用いたイリドとの反応によるジヒドロ オキサジン誘導体の合成 (2017)
  • Author(s): 長谷川恵美・菅 拓也・ 添田貴宏・宇梶 裕
  • Organizer: 日本化学会 第97春季年会 (2017)
  • Place of Presentation: 慶應義塾大学 日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] Enantioselective Synthesis of γ-Lactams via Palladium-Catalyzed Carbonylation of Homoallylic Amine Derivatives (2017)
  • Author(s): PHAN, Nga Hang Thi; SUGA, Takuya; SOETA, Takahiro; UKAJI, Yutaka
  • Organizer: 日本化学会 第97春季年会 (2017)
  • Place of Presentation: 慶應義塾大学 日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] Formal Total Synthesis of Manzacidin C via Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imine (2016)
  • Author(s): Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
  • Organizer: 平成２８年度有機合成化学北陸セミナー
  • Place of Presentation: 石川県青少年センター
  • Year and Date: 2016-10-07
• [Presentation] 下矢沙央里・奥野 巧・添田貴宏・宇梶 裕 (2016)
  • Author(s): イソシアニドを用いた[4+1]付加環化反応の開発： ベンゾチオフェン誘導体の高効率的合成
  • Organizer: 平成２８年度有機合成化学北陸セミナー
  • Place of Presentation: 石川県青少年センター
  • Year and Date: 2016-10-07
• [Presentation] ピリジン骨格を有するキラルな含窒素複素環カルベンを用いた 触媒的不斉クロスベンゾイン縮合の開発 (2016)
  • Author(s): 水野 想・添田貴宏・宇梶 裕
  • Organizer: 平成２８年度有機合成化学北陸セミナー
  • Place of Presentation: 石川県青少年センター
  • Year and Date: 2016-10-07
• [Presentation] Palladium-Catalyzed Intermolecular Alkoxy-Alkoxycarbonylation of Vinylphenols (2016)
  • Author(s): Phan Thi Hang Nga・Tomoki Furuya・ Takahiro Soeta・Yutaka Ukaji
  • Organizer: 平成２８年度有機合成化学北陸セミナー
  • Place of Presentation: 石川県青少年センター
  • Year and Date: 2016-10-07
• [Presentation] 1,3-双極子を鍵とする新規Ugi型反応の開発 (2016)
  • Author(s): 添田貴宏・高下 卓・宮本祥明・宇梶 裕
  • Organizer: 第４６回複素環化学討論会
  • Place of Presentation: 金沢市歌劇座
  • Year and Date: 2016-09-26
• [Presentation] イソシアニドジクロリドを鍵中間体とした 多官能性ジヒドロオキサゾール誘導体の新規One-Pot合成 (2016)
  • Author(s): 松本 昂大・添田 貴宏・宇梶 裕
  • Organizer: 第４６回複素環化学討論会
  • Place of Presentation: 金沢市歌劇座
  • Year and Date: 2016-09-26
• [Presentation] ニトロンを配向基としたパラジウム触媒によるC-H活性化反応の開発 (2016)
  • Author(s): 長谷川恵美・野本有紗・ 添田貴宏・宇梶 裕
  • Organizer: 第４６回複素環化学討論会
  • Place of Presentation: 金沢市歌劇座
  • Year and Date: 2016-09-26
• [Presentation] イソシアニドを用いた[4+1]付加環化反応の開発： ベンゾチオフェン誘導体の高効率的合成 (2016)
  • Author(s): 下矢沙央里，奥野 巧，添田貴宏，宇梶 裕
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] イソシアネートを活用した新規Ugi型反応の開発：高効率的1,2,4-トリアジノン誘導体の合成 (2016)
  • Author(s): 高下 卓・添田貴宏・宇梶 裕
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary (2016)
  • Author(s): Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] Carboxylic Acid Free Novel Isocyanide-Based Reactions (2015)
  • Author(s): Takahiro Soeta
  • Organizer: pacifichem2015
  • Place of Presentation: ハワイ，ホノルル
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary (2015)
  • Author(s): Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
  • Organizer: 日本化学会近畿支部平成２７年度北陸地区講演会と研究発表会
  • Place of Presentation: 金沢大学
  • Year and Date: 2015-11-27
• [Presentation] 多点認識型 NHC 配位子を用いたN-スルホニルイミンへの 触媒的不斉アルキル化反応 (2015)
  • Author(s): 石坂智洋・添田貴宏・宇梶 裕
  • Organizer: 日本化学会近畿支部平成２７年度北陸地区講演会と研究発表会
  • Place of Presentation: 金沢大学
  • Year and Date: 2015-11-27
• [Presentation] ホスフィン酸を活性化剤とした新規Ugi型反応の開発 (2015)
  • Author(s): 高下 卓・添田貴宏・宇梶 裕
  • Organizer: 日本化学会近畿支部平成２７年度北陸地区講演会と研究発表会
  • Place of Presentation: 金沢大学
  • Year and Date: 2015-11-27
• [Presentation] アリルアルコールへのテトラヒドロフラン類の位置選択的光付加反応 (2015)
  • Author(s): 渡邊康貴・坂井飛大・前多 肇・千木昌人・添田貴宏・宇梶 裕
  • Organizer: 平成２７年度有機合成化学北陸セミナー
  • Place of Presentation: 金沢大学
  • Year and Date: 2015-11-27
• [Presentation] 多点認識型NHC配位子を用いた N-スルホニルイミンへの触媒的不斉アルキル化反応 (2015)
  • Author(s): 石坂 智洋・添田 貴宏・宇梶 裕
  • Organizer: 第45回複素環化学討論会
  • Place of Presentation: 早稲田大学
  • Year and Date: 2015-11-19
• [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary (2015)
  • Author(s): Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
  • Organizer: The Thirteenth International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: Kyoto
  • Year and Date: 2015-11-09
  • Int'l Joint Research
• [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary (2015)
  • Author(s): Tong Thi Minh Thu・添田貴宏・宇梶 裕
  • Organizer: 平成２７年度有機合成化学北陸セミナー
  • Place of Presentation: 富山
  • Year and Date: 2015-10-02
• [Presentation] 多点認識型NHC配位子を用いたN-スルホニルイミンへの 触媒的不斉アルキル化 (2015)
  • Author(s): 石坂智洋・添田貴宏・宇梶 裕
  • Organizer: 平成２７年度有機合成化学北陸セミナー
  • Place of Presentation: 富山
  • Year and Date: 2015-10-02
• [Presentation] ホスフィン酸を活性化剤とした新規Ugi型反応の開発 (2015)
  • Author(s): 高下 卓・添田貴宏・宇梶 裕
  • Organizer: 平成２７年度有機合成化学北陸セミナー
  • Place of Presentation: 富山
  • Year and Date: 2015-10-02
• [Presentation] アリルアルコールへのテトラヒドロフラン類の位置選択的光付加反応 (2015)
  • Author(s): 渡邊康貴・坂井飛大・前多 肇・千木昌人・添田貴宏・宇梶 裕
  • Organizer: 平成２７年度有機合成化学北陸セミナー
  • Place of Presentation: 富山
  • Year and Date: 2015-10-02