Development of novel cycloaddition reactions of 2-azaallyl radical cations with multiple bonded compounds
Project/Area Number |
18K05111
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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Research Institution | Kitasato University |
Principal Investigator |
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Project Period (FY) |
2018-04-01 – 2021-03-31
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Project Status |
Completed (Fiscal Year 2020)
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Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2018: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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Keywords | 光付加環化反応 / ベンゾフェノン / イリジウム錯体 / 光誘起電子移動 / プロトン移動 / α-アミノアルキルラジカル / 2-アザアリルラジカルカチオン / 含窒素複素環式化合物 / 光増感 / 光付加環化 / 電子移動 / α-アミノアルキルラジカル / ニトロン / α,β-不飽和イミド / イミン / エネルギー移動 / ラジカル / ジアミノメタン / 多重結合性分子 / 付加環化反応 |
Outline of Final Research Achievements |
This research project has been successfully provided the following achievements: (1) the development of a formal [3+3] photo-cycloaddition reactions of nitrones with N,N,N',N’-tetraalkyldiaminomethanes by using benzophenone derivatives as a photo-sensitizer, (2) the development of a formal [3+2] photo-cycloaddition reactions of imines with the diaminomethanes by using Ir(III) complex photo-sensitizers, (3) the development of a formal [3+2] photo-cycloadditions of α,β-unsaturated imide with the diaminomethanes by using by using the Ir(III) complexes, (4) the development of a formal [4+2] photo-cycloaddition reactions of α,β-unsaturated imide with N,N-dialkylanilines by using the Ir(III) complexes, (5) the elucidation of photophysical properties of the Ir(III) complexes, (6) the mechanistic study for photo-cycloaddition reactions by using computational methods. However, a reaction intermediate has been detected instead of fail to detect 2-azaally radical cation.
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Academic Significance and Societal Importance of the Research Achievements |
光照射下における2-アザアリルラジカルカチオンもしくは 2-アザアリルラジカルカチオン等価体特有の反応は、新規含窒素飽和複素環骨格を一挙に構築できる。したがって本反応は、新規含窒素飽和複素環を必要とする創薬化学の分野に応用され、新薬創出の一助となる可能性がある。また2-アザアリルラジカルカチオンは、π結合を有するラジカルカチオン種の中でもその構造的特徴と物理化学的性質は未知であるに等しい。したがって、この化学種を分光化学的により捕捉し構造解析を成功させ、さらにその生成機構と物理化学的性質を明らかにすることができれば、有機合成化学の基礎を拡充させることができる。
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Report
(4 results)
Research Products
(35 results)
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[Journal Article] Visible-Light-Induced Synthesis of 1,2,3,4-Tetrahydroquinolines via Formal [4+2] Cycloaddition of Acyclic α,β-Unsaturated Amides and Imides with N,N-Dialkylanilines2021
Author(s)
Kennosuke Itoh, Shun-ichi Nagao, Ken Tokunaga, Shigeto Hirayama, Fumika Karaki, Takaaki Mizuguchi, Kenichiro Nagai, Noriko Sato, Mitsuaki Suzuki, Masashi Hashimoto, Hideaki Fujii
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Journal Title
Chem. Eur. J.
Volume: 27
Issue: 16
Pages: 5171-5179
DOI
Related Report
Peer Reviewed
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[Journal Article] Synthesis of 1,2,5-Oxadiazinane Derivatives by Photochemical Cycloaddition of Nitrones with Diaminomethanes2020
Author(s)
Itoh K, Takashino A, Ohtsuka A, Kobe M, Sawamura S, Kato R, Hirayama S, Karaki F, Mizuguchi T, Sato N, Tokunaga K, Toda Y, Suga H, Ishida H, Fujii H
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Journal Title
ChemPhotoChem
Volume: Early view
Issue: 6
Pages: 388-392
DOI
Related Report
Peer Reviewed
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[Journal Article] Novel asymmetric photodimerization reaction of coumarin derivatives bearing a chiral 2- oxazolidinone auxiliary2019
Author(s)
Itoh K, Odate F, Karikomi T, Obe K, Miyamori T, Kamiya H, Yoza K, Nagai K, Fujii H, Suga H, Tokunaga K
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Journal Title
RSC Adv.
Volume: 9
Issue: 22
Pages: 12365-12369
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] The Practical Synthesis of Dissymmetrical 1,3,5-Trioxazatriquinane Derivatives Comprised of Three Distinct Carbonyl Compounds2019
Author(s)
Hirayama S, Obayashi K, Wada N, Ohyama K, Fuku S, Koyano K, Karaki F, Itoh K, Nagase H, Fujii H
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Journal Title
Heterocycles
Volume: 99
Issue: 2
Pages: 1003-1019
DOI
Related Report
Peer Reviewed
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[Journal Article] Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system2019
Author(s)
Hiroyuki Suga, Masahiro Yoshiwara, Takaaki Yamaguchi, Takashi Bando, Mizuki Taguchi, Ayano Inaba, Yuichi Goto, Ayaka Kikuchi, Kennosuke Itoh, Yasunori Toda
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Journal Title
Chemical Communications
Volume: 55
Issue: 11
Pages: 1552-1555
DOI
Related Report
Peer Reviewed
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[Journal Article] Lewis Acid Catalysis in Intermolecular [2+2] Photocycloaddition of Coumarin-3-carboxamide Bearing 2-Oxazolidinone Auxiliary with n-Propyl Vinyl Ether and Vinyl Pivalate2018
Author(s)
Itoh, K.; Matsuura, J.; Kamiya, H.; Kudo, R.; Takahashi, Y.; Hashimoto, Y.; Yoza, K.; Tokunaga, K.; Fujii, H.; Suga, H.
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Journal Title
Heterocycles
Volume: 97
Issue: 1
Pages: 591-591
DOI
Related Report
Peer Reviewed
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[Journal Article] Three-Component Reactions of Diazoesters, Aldehydes, and Imines Using a Dual Catalytic System Consisting of a Rhodium(II) Complex and a Lewis Acid2018
Author(s)
Yasunori Toda, Wakatake Kaku, Makoto Tsuruoka, Sho Shinogaki, Tomoka Abe, Hideaki Kamiya, Ayaka Kikuchi, Kennosuke Itoh, Hiroyuki Suga
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Journal Title
Org. Lett.
Volume: 20
Issue: 9
Pages: 2659-2662
DOI
Related Report
Peer Reviewed
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[Presentation] 可視光により誘起される鎖状 α,β-不飽和カルボニル化合物と N,N-ジアルキルアニリンの形式的 [4+2] 付加環化反応による テトラヒドロキノリン合成2020
Author(s)
伊藤謙之介, 長尾駿一, 徳永 健, 水口貴章, 唐木文霞, 平山重人, 鈴木光明, 橋本雅司, 藤井秀明
Organizer
第 49 回複素環化学討論会
Related Report
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[Presentation] Photo-induced formal [3+3] cycloaddition reactions of nitrones with diaminomethanes2019
Author(s)
Itoh K, Takashino A, Ohtsuka A, Kobe M, Sawamura S, Kato R, Hirayama S, Karaki F, Mizuguchi T, Tokunaga K, Toda Y, Suga H, Ishida H, Fujii H
Organizer
International Congress on Pure & Applied Chemistry (ICPAC) Yangon Myanmar
Related Report
Int'l Joint Research / Invited
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[Presentation] Photo-induced formal [3+3] cycloaddition Reactions of Nitrones with Diaminomethanes2018
Author(s)
Atsushi Takashino, ○Kennosuke Itoh, Atsushi Ohtsuka, Mizuki Kobe, Ryo Kato, Takaaki Mizuguchi, Fumika Karaki, Shigeto Hirayama, Hiroyuki Suga, Hitoshi Ishida, Hideaki Fujii
Organizer
The 14th International Kyoto Conference on New Aspects of Organic Chemistry
Related Report
Int'l Joint Research
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