Development of One-pot Synthesis of Differentially Polysubstituted Benzenes with Various Functional Groups and its Application

• Project/Area Number: 25410051
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Osaka Prefecture University
• Principal Investigator: SONODA MOTOHIRO 大阪府立大学, 生命環境科学研究科, 准教授 (90314400)
• Project Period (FY): 2013-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 多置換ベンゼン / Diels-Alder反応 / 開環芳香族化 / ワンポット合成 / フラン / ワンポット反応 / ヘテロ芳香族化合物 / ヒドロキシ安息香酸 / ヒドロキシアントラニル酸

Outline of Final Research Achievements

One-pot synthesis of differentially polysubstituted benzenes with some functional groups owing heteroatoms was investigated. Diels-Alder reaction of 2-alkylfuran with methyl 3-bromopropiolate and the subsequent ring-opening aromatization of the formed 7-oxanorbornadienes promoted by silica gel or FeCl3 gave 2-bromo-3-hydroxybenzoate derivatives in one-pot. Further functionalization reactions including intramolecular cyclization using the polysubstituted benzenes were also performed.

Research Products

• [Journal Article] A Rapid Access to Substituted Oxazoles via PIFA-mediated Oxidative Cyclization of Enamides (2017)
  • Author(s): Kamiya, Midori; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: Tetrahedron Volume: 73 Issue: 9 Pages: 1247-1254
  • DOI: 10.1016/j.tet.2017.01.027
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Facile Synthesis of Phenanthridinone Alkaloids via Suzuki-Miyaura Cross-coupling (2017)
  • Author(s): Kuwata, Yoshiyuki; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: Journal of Heterocyclic Chemistry Volume: 54 Issue: 2 Pages: 1645-1651
  • DOI: 10.1002/jhet.2725
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Mechanistic Study of Silica-gel or FeCl3-promoted Ring-opening Aromatization of 7-Oxanorborna-2,5-dienes Affording 2-Bromo-3-hydroxybenzoate Derivatives (2017)
  • Author(s): Sonoda, Motohiro; Ikeda, Ayu; Shinohara, Hiroyuki; Hayagane, Naoya; Ogawa, Akiya; Tanimori Shinji
  • Journal Title: Research on Chemical Intermediates Volume: 印刷中
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Proline-Mediated Transition Metal-Free Access to 1H-Indazolones from 2-Halobenzohydrazides (2016)
  • Author(s): Tsujii, Miho; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: The Journal of Organic Chemistry Volume: 81 Issue: 15 Pages: 6766-6773
  • DOI: 10.1021/acs.joc.6b00651
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A Facile and Rapid Access to Resveratrol Derivatives and their Radioprotective Activity (2016)
  • Author(s): Uzura, Saori; Sekine-Suzuki, Emiko; Nakanishi, Ikuo; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 26 Issue: 16 Pages: 3886-3891
  • DOI: 10.1016/j.bmcl.2016.07.018
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Oxone-mediated Facile Access to Substituted Pyrazoles (2016)
  • Author(s): Kashiwa, Mitsuhiro; Kuwata, Yoshiyuki; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: Tetrahedron Volume: 72 Issue: 2 Pages: 304-311
  • DOI: 10.1016/j.tet.2015.11.035
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] One-Pot Synthesis of 3-Hydroxyanthranilate Derivatives Using Furans, Bromoalkyne, and Secondary Amines (2015)
  • Author(s): Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Okushima, Shunsuke; Tanimori, Shinji; Ogawa, Akiya
  • Journal Title: Tetrahedron Letters Volume: 56 Issue: 19 Pages: 2500-2503
  • DOI: 10.1016/j.tetlet.2015.03.098
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Facile Access to 1H-Indazoles through Iodobenzene-catalyzed C-H Amination under Mild, Transition-metal-free Conditions (2014)
  • Author(s): Kashiwa, Mitsuhiro; Sonoda, Motohiro; Tanimori, Shinji
  • Journal Title: European Journal of Organic Chemistry Volume: (22) Issue: 22 Pages: 4720-4723
  • DOI: 10.1002/ejoc.201402488
  • Peer Reviewed
• [Journal Article] Silica gel-promoted Convenient Synthesis of 2-Bromo-3-hydroxybenzoate Derivatives (2014)
  • Author(s): Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya
  • Journal Title: Tetrahedron Letters Volume: 55 Issue: 38 Pages: 5302-5305
  • DOI: 10.1016/j.tetlet.2014.07.084
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A Convenient Hydroiodination of Alkynes Using I2/PPh3/H2O and Its Application to the One-pot Synthesis of Trisubstituted Alkenes via Iodoalkenes Using Pd-catalyzed Cross-coupling Reactions (2014)
  • Author(s): Kawaguchi, Shin-ichi; Gonda, Yuhei; Masuno, Haruna; Vu, Hue Thi; Yamaguchi, Kohtaro; Shinohara, Hiroyuki; Sonoda, Motohiro; Ogawa, Akiya
  • Journal Title: Tetrahedron Letters Volume: 55 Issue: 50 Pages: 6779-6783
  • DOI: 10.1016/j.tetlet.2014.10.039
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Regioselective Monoarylations of 2-Phenylbenzimidazoles via Ruthenium-catalyzed C-H Bond Functionalizations (2014)
  • Author(s): Kobayashi, Yasuyuki; Kashiwa, Mitsuhiro; Sonoda, Motohiro; Kirihata, Mitsunori; Tanimori, Shinji
  • Journal Title: Synthesis Volume: 46 Issue: 23 Pages: 3185-3190
  • DOI: 10.1055/s-0034-1379013
  • Peer Reviewed
• [Journal Article] Palladium-catalyzed Oxidative Homocoupling Reaction of Terminal Acetylenes using trans-Bidentatable 1-(2-Pyridylethynyl)-2-(2-thienylethynyl)benzene (2013)
  • Author(s): Atobe, Shingo; Sonoda, Motohiro; Suzuki, Yuki; Yamamoto, Takuya; Masuno, Haruna; Shinohara, Hiroyuki; Ogawa, Akiya
  • Journal Title: Research on Chemical Intermediates Volume: 39 Issue: 1 Pages: 359-370
  • DOI: 10.1007/s11164-012-0654-2
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Perfluoroalkyl Phosphine Ligands: Photoinduced Reaction of Diphosphines with Perfluoroalkyl Iodides (2013)
  • Author(s): Kawaguchi, Shin-ichi; Minamida, Yoshiaki; Ohe, Takashi; Nomoto, Akihiro; Sonoda, Motohiro; Ogawa, Akiya
  • Journal Title: Angewandte Chemie, International Edition Volume: 52 Issue: 6 Pages: 1748-1752
  • DOI: 10.1002/anie.201207383
  • Peer Reviewed
• [Journal Article] An Efficient and Highly Selective Carbonylative Bisthiolation of Internal Alkynes with Organic Disulfides Catalyzed by [Co2(CO)8] (2013)
  • Author(s): Y. Higuchi, S. Higashimae, T. Tamai, A. Nomoto, M. Sonoda and A. Ogawa
  • Journal Title: Chemistry Letters Volume: 42 Issue: 10 Pages: 1303-1304
  • DOI: 10.1246/cl.130441
  • NAID: 10031201346
  • Peer Reviewed
• [Presentation] エナミドの分子内酸化的カップリングを用いたオキサゾール誘導体の効率的合成 (2017)
  • Author(s): 神谷緑、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会2017年度京都大会
  • Place of Presentation: 京都女子大学
  • Year and Date: 2017-03-17
• [Presentation] ボタンボウフウの生理活性成分イソサミジンの合成研究 (2017)
  • Author(s): 木下麻美、阪口祐貴、赤川貢、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会2017年度京都大会
  • Place of Presentation: 京都女子大学
  • Year and Date: 2017-03-17
• [Presentation] Proline-Catalyzed Transition-Metal-Free Synthesis of Biaryls and Indazolones (2016)
  • Author(s): Wataru Ueno, Miho Tsujii, Motohiro Sonoda, and Shinji Tanimori
  • Organizer: The Forth OPU-TKU International Symposium on Frontier Chemistry and Materials for 21st Chemistry
  • Place of Presentation: Tamkang University
  • Year and Date: 2016-11-20
  • Int'l Joint Research
• [Presentation] Hypervalent iodine-mediated oxidative coupling of hydrazinopyridine with aromatics (2016)
  • Author(s): Tatsufumi Akiyama, Motohiro Sonoda, and Shinji Tanimori
  • Organizer: The Forth OPU-TKU International Symposium on Frontier Chemistry and Materials for 21st Chemistry
  • Place of Presentation: Tamkang University
  • Year and Date: 2016-11-20
  • Int'l Joint Research
• [Presentation] フラン類のDiels-Alder反応を利用したヒドロキシ安息香酸エステル誘導体のワンポット合成 (2016)
  • Author(s): 中西ひろ海、園田素啓、池田安裕、篠原広幸、早金直哉、小川昭弥、谷森紳治
  • Organizer: 第5回 JACI/GSCシンポジウム
  • Place of Presentation: ANAクラウンプラザホテル神戸
  • Year and Date: 2016-06-02
• [Presentation] ヒガンバナ科アルカロイドcrinasiadine類の短段階合成 (2016)
  • Author(s): 桑田祥幸、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会2016年度札幌大会
  • Place of Presentation: 札幌コンベンションセンター（北海道札幌市）
  • Year and Date: 2016-03-27
• [Presentation] 臭化オキサノルボルナジエンを利用した多置換安息香酸誘導体の合成 (2016)
  • Author(s): 池田安裕、園田素啓、篠原広幸、早金直哉、小川昭弥、谷森紳治
  • Organizer: 日本農芸化学会2016年度札幌大会
  • Place of Presentation: 札幌コンベンションセンター（北海道札幌市）
  • Year and Date: 2016-03-27
• [Presentation] Straightforward Synthesis of Polyfunctionalized Benzoate Derivatives Using 7-Oxanorbornadienes (2015)
  • Author(s): Motohiro Sonoda, Hiroyuki Shinohara, Ayu Ikeda, Naoya Hayagane, Akiya Ogawa, and Shinji Tanimori
  • Organizer: The Third OPU-TKU International Symposium on Frontier Chemistry and Materials for 21st Chemistry
  • Place of Presentation: 大阪府立大学（大阪府堺市）
  • Year and Date: 2015-11-19
  • Int'l Joint Research / Invited
• [Presentation] Efficient Synthesis of Differentially-functionalized Benzoate Derivatives and Its Further Transformations (2015)
  • Author(s): Motohiro Sonoda, Hiroyuki Shinohara, Ayu Ikeda, Naoya Hayagane, Akiya Ogawa, and Shinji Tanimori
  • Organizer: The 13th International Kyoto Conference on New Aspect of Organic Chemistry
  • Place of Presentation: リーガロイヤルホテル京都（京都府京都市）
  • Year and Date: 2015-11-09
  • Int'l Joint Research
• [Presentation] エナミドの分子内酸化的カップリングによるオキサゾール誘導体の効率的合成 (2015)
  • Author(s): 神谷緑、園田素啓、谷森紳治
  • Organizer: 第41回反応と合成の進歩シンポジウム
  • Place of Presentation: 近畿大学（大阪府東大阪市）
  • Year and Date: 2015-10-26
• [Presentation] レスベラトロール誘導体の合成とそのラジカル捕捉活性ならびに放射線防護活性評価 (2015)
  • Author(s): 卯津羅早織、園田素啓、谷森紳治、関根絵美子、中西郁夫
  • Organizer: 2015年度日本農芸化学会中部・関西支部合同大会
  • Place of Presentation: 富山県立大（富山県射水市）
  • Year and Date: 2015-09-19
• [Presentation] 大豆イソフラボン代謝産物equolのエナンチオ選択的合成研究 (2015)
  • Author(s): 木下麻美、齋藤雄輔、園田素啓、谷森紳治
  • Organizer: 2015年度日本農芸化学会中部・関西支部合同大会
  • Place of Presentation: 富山県立大（富山県射水市）
  • Year and Date: 2015-09-19
• [Presentation] Synthesis of quinoxaline derivatives and its fragrance evaluation (2015)
  • Author(s): 今西望愛、園田素啓、谷森紳治、宮里博成、杉本圭一郎
  • Organizer: 第59回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 近畿大学（大阪府東大阪市）
  • Year and Date: 2015-09-05
• [Presentation] キノキサリン誘導体の合成と香気評価 (2015)
  • Author(s): 今西望愛、園田素啓、谷森紳治、宮里博成、杉本圭一郎
  • Organizer: 日本農芸化学会関西支部第490回講演会・ミニシンポジウム
  • Place of Presentation: 大阪府立大学（大阪府堺市）
  • Year and Date: 2015-07-04
• [Presentation] 置換基の特性を利用した多官能性芳香族化合物の省力的合成法の開発 (2015)
  • Author(s): 園田素啓
  • Organizer: 大阪府立大学21世紀科学研究機構 ライブセルイメージング研究所第30回セミナー
  • Place of Presentation: 大阪府立大学（大阪府堺市）
  • Year and Date: 2015-05-07
• [Presentation] L-プロリンを触媒に用いたインダゾロン誘導体のメタルフリー合成法の開発 (2015)
  • Author(s): 辻井美穂、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会2015年度岡山大会
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] オキソンを用いた酸化的分子内C-Nカップリングによる多置換ピラゾールの効率的合成 (2015)
  • Author(s): 柏充裕、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会2015年度岡山大会
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] フラン、アルキン、二級アミンを用いた三成分カップリングによる3－ヒドロキシアントラニル酸エステルのワンポット合成 (2015)
  • Author(s): 園田素啓、篠原広幸、早金直哉、北翔太、小川昭弥、谷森紳治
  • Organizer: 日本農芸化学会2015年度岡山大会
  • Place of Presentation: 岡山大学
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Facile and Efficient Functionalization of 2-Bromo-3-hydroxybenzoate Derivatives (2014)
  • Author(s): Naoya Hayagane, Motohiro Sonoda, Hiroyuki Shinohara, Shota Kita, Shinji Tanimori, and Akiya Ogawa
  • Organizer: The 9th International Symposium on Integrated Synthesis 2014 (ISIS-9)
  • Place of Presentation: 淡路夢舞台国際会議場
  • Year and Date: 2014-11-14 – 2014-11-15
• [Presentation] One-pot Synthesis of Trisubstituted Alkenes via Hydroiodination of Alkynes with I2/PPh3/H2O (2014)
  • Author(s): Yuhei Gonda, Shin-ichi Kawaguchi, Motohiro Sonoda, Akihiro Nomoto, and Akiya Ogawa
  • Organizer: The 9th International Symposium on Integrated Synthesis 2014 (ISIS-9)
  • Place of Presentation: 淡路夢舞台国際会議場
  • Year and Date: 2014-11-14 – 2014-11-15
• [Presentation] 鈴木－宮浦カップリング反応を利用したフェナントリドンの新規合成法とヒガンバナ科アルカロイド類への応用 (2014)
  • Author(s): 桑田祥幸、中川直道、竹田一貴、園田素啓、谷森紳治
  • Organizer: 第56回天然有機化合物討論会
  • Place of Presentation: 高知県立県民文化ホール
  • Year and Date: 2014-10-15 – 2014-10-17
• [Presentation] 酸化的Heck反応を用いたレスベラトロール類縁体の簡便合成 (2014)
  • Author(s): 卯津羅早織、諌山篤、園田素啓、谷森紳治
  • Organizer: 日本農芸化学会関西支部大会（第486回講演会）
  • Place of Presentation: 奈良先端科学技術大学院大学
  • Year and Date: 2014-09-20
• [Presentation] シリカゲルまたは塩化鉄触媒を用いたブロモ安息香酸エステル誘導体の簡便合成とその応用 (2014)
  • Author(s): 早金直哉、園田素啓、篠原広幸、北翔太、小川昭弥
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学
• [Presentation] アルキンのヒドロヨウ素化反応とクロスカップリング反応を組み合わせた置換アルケン類のワンポット合成 (2014)
  • Author(s): 権田悠平、川口真一、枡野晴菜、園田素啓、小川昭弥
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学
• [Presentation] Convenient Synthesis of 2-Bromo-3-hydroxybenzoate Derivatives and Its Functionalization (2013)
  • Author(s): Hiroyuki Shinohara, Motohiro Sonoda, Naoya Hayagane, and Akiya Ogawa
  • Organizer: 17th IUPAC Symposium on Organometallic Chemistry Directed towards Organic Synthesis
  • Place of Presentation: コロラド州立大学、アメリカ合衆国
• [Presentation] Pd-catalyzed Coupling of Terminal Alkynes Using trans-Bidentate 1-(2-Pyridylethynyl)-2-(2-thienylethynyl)benzene as a Ligand (2013)
  • Author(s): Motohiro Sonoda, Shingo Atobe, Yuki Suzuki, Haruna Masuno, and Akiya Ogawa
  • Organizer: 17th IUPAC Symposium on Organometallic Chemistry Directed towards Organic Synthesis
  • Place of Presentation: コロラド州立大学、アメリカ合衆国
• [Presentation] シリカゲルまたは塩化鉄触媒を用いたヒドロキシ安息香酸エステル誘導体の合成 (2013)
  • Author(s): 早金直哉、園田素啓、篠原広幸、小川昭弥
  • Organizer: 第60回有機金属化学討論会
  • Place of Presentation: 学習院大学
• [Presentation] フラン類のDiels-Alder反応を利用した多置換安息香酸エステル誘導体の合成 (2013)
  • Author(s): 篠原広幸、園田素啓、早金直哉、小川昭弥
  • Organizer: 第43回複素環化学討論会
  • Place of Presentation: 長良川国際会議場
• [Presentation] Fixation of CO2 by Amines and Synthesis of Carbamoyl Derivatives (2013)
  • Author(s): Shota Kita, Motohiro Sonoda, Haruna Masuno, and Akiya Ogawa
  • Organizer: The First OPU-TKU International Symposium on Frontier Chemistry and Materials for 21st Chemistry
  • Place of Presentation: 大阪府立大学
• [Presentation] I2-PPh3複合系を用いたアルキンのヒドロヨウ素化反応とそれを利用したビニル化合物のワンポット合成 (2013)
  • Author(s): 権田悠平、川口真一、枡野晴菜、園田素啓、小川昭弥
  • Organizer: 第40回有機典型元素化学討論会
  • Place of Presentation: 近畿大学
• [Presentation] シリカゲルを用いた2-ブロモ-3-ヒドロキシ安息香酸エステル誘導体の簡便合成 (2013)
  • Author(s): 篠原広幸、園田素啓、早金直哉、小川昭弥
  • Organizer: 第40回有機典型元素化学討論会
  • Place of Presentation: 近畿大学