Development of new synthetic reactions utilizing high reactivity of ethenetricarboxylates

• Project/Area Number: 20550041
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Nara University of Education
• Principal Investigator: YAMAZAKI Shoko Nara University of Education, 教育学部, 教授 (50182481)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000); Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2008: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 合成反応 / 効率的結合形成 / ルイス酸 / エテントリカルボン酸エステル / アミノアセタール / ピペリジン / ピロリジン / アレン / ケトマロン酸エチル / インデン / 2-アミノベンズアルデヒド / テトラヒドロキノリン / インドール / γ-ラクトン / トリフロロメチル基 / プロパルギルアルコール / シクロブタン / 2-エチニルアニリン / キノリン

Research Abstract

New efficient cycloaddition reactions utilizing high reactivity of ethenetricarboxylates has been developed. Lewis acid promoted reaction of ethenetricarboxylates with substituted propargyl alcohols, ethynyl anilines, aminobezaldehydes, aminoacetals, and allenes gave nitrogen or oxygen-containing cyclic and carbocyclic compounds. These reactions represent efficient ways to construct potentially useful compounds.

Research Products

• [Journal Article] Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes : Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction. (2010)
  • Author(s): Yamazaki, S., Yamamoto, Y., Fukushima, Y., Takebayashi, M., Ukai, T., Mikata, Y.
  • Journal Title: J.Org.Chem. 75 Pages: 5216-5222
  • Peer Reviewed
• [Journal Article] Zn(OTf)2-Catalyzed Reactions of Ethene-tricarboxylates with 2-Aminobenzaldehydes Leading to Tetrahydroquinoline Derivatives. (2010)
  • Author(s): Yamazaki, S., Takebayashi, M., Miyazaki, K.
  • Journal Title: J.Org.Chem. 75 Pages: 1188-1196
  • Peer Reviewed
• [Journal Article] Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes : Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction. (2010)
  • Author(s): Yamazaki, S.; Yamamoto, Y.; Fukushima, Y.; Takebayashi, M.; Ukai, T.; Mikata, Y.
  • Journal Title: J.Org.Chem. Volume: 75 Pages: 5216-5222
  • Peer Reviewed
• [Journal Article] Correlation between the Rate Order and the Number of Molecules in the Reaction of Trimethyl Phosphite with Water in Acetonitrile Solvent (2010)
  • Author(s): Yamabe, S.; Tsuchida, N.; Yamazaki, S.
  • Journal Title: J.Phys.Chem.A Volume: 114 Pages: 11699-11707
  • Peer Reviewed
• [Journal Article] Zn(OTf)_2-Catalyzed Reactions of Ethenetricarboxylates with 2-Aminobenzaldehydes Leading to Tetrahydroquinoline Derivatives. (2010)
  • Author(s): Yamazaki, S. ; Takebayashi, M. ; Miyazaki, K.
  • Journal Title: J.Org.Chem. 75 Pages: 1188-1196
  • Peer Reviewed
• [Journal Article] π Complexes in benzidine rearrangement. (2009)
  • Author(s): Yamabe, S., Nakata, H., Yamazaki, S.
  • Journal Title: Org.Biomol. Chem. 7 Pages: 4631-4640
  • Peer Reviewed
• [Journal Article] A remarkable difference in the deprotonation steps of the Friedel-Crafts acylation and alkylation reactions. (2009)
  • Author(s): Yamabe, S., Yamazaki, S.
  • Journal Title: J.Phys.Org.Chem. 22 Pages: 1094-1103
  • Peer Reviewed
• [Journal Article] Zinc-Catalyzed Reactions of Ethenetricarboxylates with 2-(Trimethyl-silylethynyl)anilines Leading to Bridged Quinoline Derivatives (2009)
  • Author(s): Yamazaki, S., Morikawa, S., Miyazaki, K., Takebayashi, M., Yamamoto, Y., Morimoto, T., Kakiuchi, K., Mikata, Y.
  • Journal Title: Org.Lett. 11 Pages: 2796-2799
  • Peer Reviewed
• [Journal Article] Enantioselective Friedel-Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives (2009)
  • Author(s): Yamazaki, S., Kashima, S., Kuriyama, T., Iwata, Y., Morimoto, T., Kakiuchi, K.
  • Journal Title: Tetrahedron : Asymmetry 20 Pages: 1224-1234
  • Peer Reviewed
• [Journal Article] Three competitive transition states in the benzoin condensation compared to the clear rate-determining step in the Cannizzaro reaction (2009)
  • Author(s): Yamabe, S., Yamazaki, S.
  • Journal Title: Org.Biomol. Chem. 7 Pages: 951-961
  • Peer Reviewed
• [Journal Article] Lewis acid-promoted reactions of ethenetricarboxylates with γ-CF_3-substituted propargyl alcohols (2009)
  • Author(s): Yamazaki, S., Yamamoto, Y., Mikata, Y.
  • Journal Title: Tetrahedron 65 Pages: 1988-1994
  • Peer Reviewed
• [Journal Article] Efficient synthesis of heterocyclic compounds using ethenetricarboxylic acid diesters (2009)
  • Author(s): Yamazaki, S., Iwata, Y., Fukushima, Y.
  • Journal Title: Org.Biomol. Chem. 7 Pages: 655-659
  • Peer Reviewed
• [Journal Article] πComplexes in benzidine rearrangement. (2009)
  • Author(s): Yamabe, S. ; Nakata, H. ; Yamazaki, S.
  • Journal Title: Org.Biomol.Chem. 7 Pages: 4631-4640
  • Peer Reviewed
• [Journal Article] A remarkable difference in the deprotonation steps of the Friedel-Crafts acylation and alkylation reactions. (2009)
  • Author(s): Yamabe, S. ; Yamazaki, S.
  • Journal Title: J.Phys.Org.Chem. 22 Pages: 1094-1103
  • Peer Reviewed
• [Journal Article] Zinc-Catalyzed Reactions of Ethenetricarboxylates with 2-(Trimethylsilylethynyl)anilines Leading to Bridged Quinoline Derivatives (2009)
  • Author(s): Yamazaki, S. ; Morikawa, S. ; Miyazaki, K. ; Takebayashi, M. ; Yamamoto, Y. ; Morimoto, T. ; Kakiuchi, K. ; Mikata, Y.
  • Journal Title: Org.Lett. 11 Pages: 2796-2799
  • Peer Reviewed
• [Journal Article] Enantioselective Friedel-Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives (2009)
  • Author(s): Yamazaki, S. ; Kashima, S. ; Kuriyama, T. ; Iwata, Y. ; Morimoto, T. ; Kakiuchi, K.
  • Journal Title: Tetrahedron : Asymmetry 20 Pages: 1224-1234
  • Peer Reviewed
• [Journal Article] Three competitive transition states in the benzoin condensation compared to the clear rate-determining step in the Cannizzaro reaction (2009)
  • Author(s): Yamabe, S., Yamazaki, S.
  • Journal Title: Org. Biomol. Chem. 7 Pages: 951-961
  • Peer Reviewed
• [Journal Article] Efficient synthesis of heterocyclic compounds using ethenetricarboxylicacid diesters (2009)
  • Author(s): Yamazaki, S., Iwata, Y., Fukushima, Y.
  • Journal Title: Org. Biomol. Chem. 7 Pages: 655-659
  • Peer Reviewed
• [Journal Article] A new mechanism for the addition of alcohols to disilenes revealed by DFT and ONIOM calculations (2008)
  • Author(s): Yamabe, S., Mizukami, N., Tsuchida, N., Yamazaki, S.
  • Journal Title: J.Organomet. Chem. 693 Pages: 1335-1345
  • Peer Reviewed
• [Journal Article] A new mechanism for the Favorskii rearrangement, Tsuchida (2008)
  • Author(s): Tsuchida, N., Yamazaki, S., Yamabe, S.
  • Journal Title: Org.Biomol. Chem. 6 Pages: 3109-3117
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Methylenetetra-hydrofurans and Methylenepyrrolidines by Formal [3+2] Cycloadditions of Propargyl Substrates (2008)
  • Author(s): Yamazaki, S.
  • Journal Title: Chem.Eur.J. 14 Pages: 6026-6036
  • Peer Reviewed
• [Journal Article] A new mechanism for the addition of alcohols to disilenes revealed by DFT and ONIOM calculations (2008)
  • Author(s): Yamabe, S., Mizukami, N., Tsuchida, N., Yamazaki, S.
  • Journal Title: J. Organomet. Chem. 693 Pages: 1335-1345
  • Peer Reviewed
• [Journal Article] A new mechanism for the Favorskii rearrangement (2008)
  • Author(s): Tsuchida, N., Yamazaki, S., Yamabe, S.
  • Journal Title: Org. Biomol. Chem. 6 Pages: 3109-3117
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Methylenetetrahydrofurans and Methylenepyrrolidines by Formal [3+2] Cycloadditions of Propargyl Substrates (2008)
  • Author(s): Yamazaki, S.
  • Journal Title: Chem. Eur. J. 14 Pages: 6026-6036
  • Peer Reviewed
• [Presentation] ルイス酸触媒によるアリールアレンとケトマロン酸エチルの付加-環化反応によるインデン合成 (2011)
  • Author(s): 山崎祥子・○福島悠吾・鵜飼哲真
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2011-03-29
• [Presentation] 四塩化チタンにより促進されるアミノアセタールとエテントリカルボン酸エステルとの反応による含窒素ヘテロ環の合成 (2011)
  • Author(s): 山崎祥子・○竹林聖央
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2011-03-27
• [Presentation] Lewis acid-promoted Reactions of Ethenetricarboxylates with Allenes : Efficient Synthesis of Indenes via Conjugate Addition/Friedel-Crafts Reaction (2010)
  • Author(s): ○山崎祥子, 山本優子, 福島悠吾, 竹林聖央, 鵜飼哲真
  • Organizer: 18th International Conference on Organic Synthesis (ICOS-18)
  • Place of Presentation: Bergen, Norway
  • Year and Date: 2010-08-03
• [Presentation] Lewis acid-promoted Reactions of Ethenetricarboxylates with Allenes : Efficient Synthesis of Indenes via Conjugate Addition/Friedel-Crafts Reaction (2010)
  • Author(s): S.Yamazaki, Y.Yamamoto, Y.Fukushima, M.Takebayashi, T.Ukai
  • Organizer: 18th International Conference on Organic Synthesis (ICOS-18)
  • Place of Presentation: Bergen Norway
  • Year and Date: 2010-08-03
• [Presentation] ルイス酸触媒下のエテントリカルボン酸誘導体と2-アミノベンズアルデヒドの反応によるキノリン誘導体の合成 (2010)
  • Author(s): 山崎祥子・宮崎和也・○竹林聖央・小林有
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-28
• [Presentation] ルイス酸触媒によるエテントリカルボン酸エステルとアリールアレンの共役付加/フリーデルクラフツ環化反応による効率的インデン合成 (2010)
  • Author(s): 山崎祥子・山本優子・○福島悠吾
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-27
• [Presentation] Zinc-catalyzed Reactions of Ethene-tricarboxylates with 2-Aminobenzaldehydes Leading to Quinoline Derivatives (2009)
  • Author(s): 山崎祥子, 竹林聖央, 宮崎和也
  • Organizer: The 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
  • Place of Presentation: Kyoto
  • Year and Date: 2009-11-10
• [Presentation] Zinc-catalyzed Reactions of Ethenetricarboxylates with 2-Aminobenzaldehydes Leading to Quinoline Derivatives (2009)
  • Author(s): Shoko Yamazaki, Masachika Takebayashi, Kazuya Miyazaki
  • Organizer: the 11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
  • Place of Presentation: Kyoto, Japan
  • Year and Date: 2009-11-10
• [Presentation] 2-アミノベンズアルデヒドとエテントリカルボン酸誘導体のタンデム反応による環形成 (2009)
  • Author(s): 山崎祥子・○宮崎和也・竹林聖央
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-08
• [Presentation] ルイス酸触媒によるエテントリカルボン酸誘導体とアレンの環化付加反応 (2009)
  • Author(s): 山崎祥子・○山本優子・福島悠吾
  • Organizer: 第53回香料・テルペンおよび精油化学に関する討論会
  • Place of Presentation: 奈良
  • Year and Date: 2009-11-08
• [Presentation] Zinc-catalyzed Reactions of Ethene-tricarboxylates with 2-(Trimethylsilylethynyl) anilines Leading to Bridged Quinoline Derivatives (2009)
  • Author(s): 山崎祥子, 森川智史, 宮崎和也, 竹林聖央, 山本優子, 森本積, 垣内喜代三
  • Organizer: 15th International IUPAC Conference on Organometallic Chemistry Directed Towards Organic Synthesis, OMCOS-15
  • Place of Presentation: Glasgow, UK
  • Year and Date: 2009-07-27
• [Presentation] Zinc-catalyzed Reactions of Ethenetricarboxylates with 2-(Trimethylsilylethynyl)anilines Leading to Bridged Quinoline Derivatives (2009)
  • Author(s): S.Yamazaki, S.Morikawa, K.Miyazaki, M.Takebayashi, Y.Yamamoto, T.Morimoto, K.Kakiuchi
  • Organizer: 15th International IUPAC Conference on Organometallic Chemistry Directed Towards Organic Synthesis, OMCOS-15
  • Place of Presentation: Glasgow, UK
  • Year and Date: 2009-07-27
• [Presentation] ルイス酸触媒によるエデントリカルボン酸誘導体とγ-CF_3置換プロパルギルアルコールの付加環化反応 (2009)
  • Author(s): 山崎祥子, 山本優子
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉県船橋市
  • Year and Date: 2009-03-30
• [Presentation] エデントリカルボン酸エステルと置換フランの触媒的エナンチオ選択的フリーデルクラフツ反応 (2009)
  • Author(s): 山崎祥子, 栗山大樹, 鹿島慎一, 岩田ゆう子
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉県船橋市
  • Year and Date: 2009-03-28
• [Presentation] 亜鉛ルイス酸触媒下のエデントリカルボン酸誘導体と2-トリメチルシリルェチニルアニリンの反応による橋掛けキノリン誘導体の合成 (2009)
  • Author(s): 山崎祥子, 宮崎和也, 竹林聖央, 山本優子
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉県船橋市
  • Year and Date: 2009-03-27
• [Presentation] Lewis acid-promoted Reactions of Ethenetricarboxylates with γ-CF3-substituted Propargyl Alcohols (2008)
  • Author(s): S.Yamazaki, ○ Y.Yamamoto, Y.Mikata
  • Organizer: The Fifth International Symposium on Integrated Synthesis (ISIS-5)
  • Place of Presentation: Kobe, Hyogo, Japan
  • Year and Date: 2008-09-06
• [Presentation] Lewis acid-promoted Reactions of Ethene-tricarboxylates with γ-CF_3-substituted Propargyl Alcohols (2008)
  • Author(s): Shoko Yamazaki. Yuko Yamamoto, Yuji Mikata
  • Organizer: The Fifth International Symposium on Integrated Synthesis (ISIS-5)
  • Place of Presentation: Kobe, Hyogo, Japan
  • Year and Date: 2008-09-06
• [Presentation] Efficient Synthesis of Heterocyclic Compounds using Ethenetricarboxylic Acid Diesters (2008)
  • Author(s): ○山崎祥子, 岩田ゆう子
  • Organizer: 17th Gordon Research Conference on Stereochemistry
  • Place of Presentation: Newport RI United States
  • Year and Date: 2008-07-31
• [Presentation] Efficient Synthesis of Heterocyclic Compounds using Ethenetricarboxylic Acid Diesters (2008)
  • Author(s): Shoko Yamazaki, Yuko Iwata
  • Organizer: 17th Gordon Research Conference on Stereochemistry
  • Place of Presentation: Newport RI United State
  • Year and Date: 2008-07-31
• [Presentation] エテントリカルボン酸ジエステルを利用した効率的ヘテロ環合成 (2008)
  • Author(s): 山崎祥子・○岩田ゆう子・角亜紀子
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-28
• [Presentation] ルイス酸触媒によるエテントリカルボン酸誘導体と置換プロパルギルアミン、アルコール類の付加環化反応 (2008)
  • Author(s): ○森川智史・山崎祥子・山本優子・森本積・垣内喜代三
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-28
• [Book] The Chemistry of Organo-magnesium Compounds(Part 1, Chapter 9)(Theoretical Studies of the Addition of RMgX to Carbonyl Compounds)(Rappoport, Z.; Marek, I.Ed.) (2008)
  • Author(s): Yamabe, S., Yamazaki, S.
  • Publisher: Wiley
• [Book] Comprehensive Heterocyclic Chemistry III(Vol.6, Chapter 6.12)(Three or Four Heteroatom Including At Least One Selenium or Tellurium.)(Katritzky, A.R.; Ramsden, C.A.; Scriven, E.F.V.; Taylor, R.J.K., Ed.) (2008)
  • Author(s): Yamazaki, S.
  • Publisher: Elsevier
• [Book] Theoretical Studies of the Addition of RMgX to Carbonyl Compounds, "The Chemistry of Organomagnesium Compounds", Rappoport, Z. ; Marek, I. Ed. Part 1, Chapter 9, p 369-402. (2008)
  • Author(s): Yamabe, S., Yamazaki, S.
  • Publisher: Wiley
• [Book] Three or Four Heteroatom Including At Least One Selenium or Tellurium. Comprehensive Heterocyclic Chemistry III, Katritzky, A. R. ; Ramsden, C. A. . ; Scriven, E. . F. V. ; Taylor, R. J. K., Ed. ; Vol. 6, Chapter 6.12 (2008)
  • Author(s): Yamazaki, S.
  • Publisher: Elsevier
• [Book] Thiepanes and Thiepines. Comprehensive Heterocyclic Chemistry III, Katritzky, A. R. ; Ramsden, C. A. ; Scriven, E. F. V. ; Taylor, R. J. K., Ed. ; Vol. 13, Chapter 13.03 (2008)
  • Author(s): Yamazaki, S.
  • Publisher: Elsevier