Synthesis of macrocycles using bis(carbonylamino)pyridine unit

• Project/Area Number: 23550140
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Polymer chemistry
• Research Institution: Seikei University
• Principal Investigator: YOKOYAMA Akihiro 成蹊大学, 理工学部, 教授 (50343637)
• Project Period (FY): 2011 – 2013
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 大環状化合物 / アミド結合

Research Abstract

4-Substituted 2,6-diaminopyridine was prepared, and condensation reaction of this compound with terephthaloyl chloride was studied for the synthesis of macrocycles. When the reaction was carried out in 1,4-dioxane at 50 degree with N-ethyldiisopropylamine as a base, the oligomers with moderate molecular weight were obtained. Separation of the crude products afforded the products with desired molecular weight.

Research Products

• [Journal Article] Synthesis of Well-Defined, Soluble Poly(3-alkyl-4-benzamide) by Chain-Growth Condensation Polymerization (2014)
  • Author(s): Yoshihiro Ohta, Makoto Karasawa, Tetsurou Niiyama, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Journal of Polymer Science, Part A: Polymer Chemistry Volume: 52 Issue: 3 Pages: 360-365
  • DOI: 10.1002/pola.27008
  • Peer Reviewed
• [Journal Article] Binaphthyl-based chiral macrocyclophanes with variously sized cavities: Dn-symmetrical structure constructed from unidirectionally-inclined rod segments (2014)
  • Author(s): Kazuto Takaishi, Tatsuya Yabe, Masanobu Uchiyama, Akihiro Yokoyama
  • Journal Title: Tetrahedron Volume: 70 Issue: 3 Pages: 730-734
  • DOI: 10.1016/j.tet.2013.11.081
  • Peer Reviewed
• [Journal Article] Successive formation of two amide linkages between two benzene rings (2013)
  • Author(s): Akihiro Yokoyama, Makoto Karasawa, Masahisa Taniguchi, Tsutomu Yokozawa
  • Journal Title: Chem. Lett. Volume: 42 Issue: 6 Pages: 641-642
  • DOI: 10.1246/cl.130143
  • NAID: 10031176035
  • Peer Reviewed
• [Journal Article] Synthesis of 2,3-Bis(halomethyl)quinoxaline Derivatives and Evaluation of Their Antibacterial and Antifungal Activities (2013)
  • Author(s): Hisato Ishikawa, Takayuki Sugiyama, Akihiro Yokoyama
  • Journal Title: Chemical and Pharmaceutical Bulletin Volume: 61 Issue: 4 Pages: 438-444
  • DOI: 10.1248/cpb.c12-01061
  • NAID: 130003360754
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] Synthesis of Well-Defined, Amphiphilic Poly(ethylene glycol)-b-Hyperbranched Polyamide (2013)
  • Author(s): Yoshihiro Ohta, Teruaki Kanou, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Journal of Polymer Science, Part A: Polymer Chemistry Volume: 51 Issue: 17 Pages: 3762-3766
  • DOI: 10.1002/pola.26762
  • Peer Reviewed
• [Journal Article] Synthesis of polystyrene-graft-poly(p-benzamide) by chain-growth condensation polymerization and radical polymerization: Improvement of thermal properties of polystyrene (2013)
  • Author(s): Yoshihiro Ohta, Tadahiko Shirakura, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Journal of Polymer Science, Part A: Polymer Chemistry Volume: 51 Issue: 8 Pages: 1887-1892
  • DOI: 10.1002/pola.26548
  • Peer Reviewed
• [Journal Article] Synthesis of well-defined, water- soluble hyperbranched polyamides by chain-growth condensation polymerization of AB_2 monomer (2012)
  • Author(s): Yoshihiro Ohta, Yusuke Kamijyo, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Polymers Volume: 4 Issue: 2 Pages: 1170-1182
  • DOI: 10.3390/polym4021170
  • Peer Reviewed
• [Journal Article] Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells (2012)
  • Author(s): Tomoko Yamaguchi, Shinya Watanabe, Yuriko Matsumura, Yoshikazu Tokuoka, Akihiro Yokoyama
  • Journal Title: Chemical and Pharmaceutical Bulletin Volume: 60 Issue: 4 Pages: 508-512
  • DOI: 10.1248/cpb.60.508
  • NAID: 130001852442
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] Three-arm star block copolymers of aromatic polyether and polystyrene from chain-growth condensation polymerization, atom transfer radical polymerization, and click reaction (2012)
  • Author(s): Yuka Yamazaki, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: J. Polym. Sci., Part A : Polym. Chem. Volume: 50 Issue: 17 Pages: 3648-3655
  • DOI: 10.1002/pola.26155
  • Peer Reviewed
• [Journal Article] Investigation of catalyst-transfer condensation polymerization for the synthesis of n-type π-conjugated polymer, poly(2-dioxaalkylpyridine-3,6-diyl) (2012)
  • Author(s): Yutaka Nanashima, Rena Shibata, Ryo Miyakoshi, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Journal of Polymer Science, Part A: Polymer Chemistry Volume: 50 Issue: 17 Pages: 3628-3640
  • DOI: 10.1002/pola.26152
  • Peer Reviewed
• [Journal Article] Oxovanadium complexes with quinoline and pyridinone ligands : Syntheses of the complexes and effect of alkyl chains on their apoptosis-inducing activity in leukemia cells (2012)
  • Author(s): Tomoko Yamaguchi, Shinya Watanabe, Yuriko Matsumura, Yoshikazu Tokuoka, Akihiro Yokoyama
  • Journal Title: Bioorg. Med. Chem. Volume: 20 Issue: 9 Pages: 3058-3064
  • DOI: 10.1016/j.bmc.2012.02.063
  • Peer Reviewed
• [Journal Article] Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives (2012)
  • Author(s): Hisato Ishikawa, Takayuki Sugiyama, Keisuke Kurita, Akihiro Yokoyama
  • Journal Title: Bioorg. Chem. Volume: 41-42 Pages: 1-5
  • DOI: 10.1016/j.bioorg.2011.12.002
  • Peer Reviewed
• [Journal Article] Synthesis of Weil-Defined Poly (2-alkoxypyridine-3,5-diyl) via Ni-Catalyst-Transfer Condensation Polymerization (2012)
  • Author(s): Yutaka Nanashima
  • Journal Title: Macromolecules Volume: 45 Issue: 5 Pages: 2609-2613
  • DOI: 10.1021/ma202756y
  • Peer Reviewed
• [Journal Article] Synthesis of Novel Blue-Light-Emitting Polypyridine (2012)
  • Author(s): Yutaka Nanashima
  • Journal Title: J.Polym.Sci., Part A : Polym.Chem. Volume: 50 Issue: 6 Pages: 1054-1061
  • DOI: 10.1002/pola.25891
  • Peer Reviewed
• [Journal Article] Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives. (2012)
  • Author(s): Hisato Ishikawa, Takayuki Sugiyama, Keisuke Kurita, Akihiro Yokoyama
  • Journal Title: Bioorg. Chem. Volume: 41-42 Pages: 1-5
  • Peer Reviewed
• [Journal Article] Oxovanadium complexes with quinoline and pyridinone ligands: Syntheses of the complexes and effect of alkyl chains on their apoptosis-inducing activity in leukemia cells. (2012)
  • Author(s): Tomoko Yamaguchi, Shinya Watanabe, Yuriko Matsumura, Yoshikazu Tokuoka, Akihiro Yokoyama
  • Journal Title: Bioorg. Med. Chem. Volume: 20 Pages: 3058-3064
  • Peer Reviewed
• [Journal Article] Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells. (2012)
  • Author(s): Tomoko Yamaguchi, Shinya Watanabe, Yuriko Matsumura, Yoshikazu Tokuoka, Akihiro Yokoyama
  • Journal Title: Chem. Pharm. Bull. Volume: 60 Pages: 508-512
  • NAID: 130001852442
  • Peer Reviewed
• [Journal Article] Synthesis of Well-Defined, Water-Soluble Hyperbranched Polyamides by Chain-Growth Condensation Polymerization of AB2 Monomer. (2012)
  • Author(s): Yoshihiro Ohta, Yusuke Kamijyo, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Polymers Volume: 4 Pages: 1170-1182
  • Peer Reviewed
• [Journal Article] Synthesis and helical properties of N-substituted p-benzamide random copolymers possessing chiral/achiral and (S)/(R) side chains (2011)
  • Author(s): Akihiro Yokoyama, Yuko Inagaki, Tomomi Ono, Tsutomu Yokozawa
  • Journal Title: J. Polym. Sci., Part A : Polym. Chem. Volume: 49 Issue: 6 Pages: 1387-1395
  • DOI: 10.1002/pola.24559
  • Peer Reviewed
• [Journal Article] Synthesis of linear and cyclic aromatic peptides with fixed conformation owing to intramolecular hydrogen bonding by condensation polymerization method (2011)
  • Author(s): Tomoyuki Ohishi, Toshiya Suzuki, Tetsurou Niiyama, Koichiro Mikami, Akihiro Yokoyama, Kosuke Katagiri, Isao Azumaya, Tsutomu Yokozawa
  • Journal Title: Tetrahedron Lett. Volume: 52 Issue: 52 Pages: 7067-7070
  • DOI: 10.1016/j.tetlet.2011.10.071
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of a Variety of Well- Defined Hyperbranched N-Alkyl and N-H Polyamides by Chain-Growth Condensa- tion Polymerization of AB_2 Monomers (2011)
  • Author(s): Yoshihiro Ohta, Yusuke Kamijyo, Shuichi Fujii, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Macromolecules Volume: 44 Issue: 13 Pages: 5112-5122
  • DOI: 10.1021/ma200980t
  • Peer Reviewed
• [Journal Article] Synthesis of poly(naphthalenecarboxamide)s with low polydispersity by chain-growth condensation polymerization (2011)
  • Author(s): Koichiro Mikami, Hiroaki Daikuhara, Jyunya Kasama, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: J. Polym. Sci., Part A : Polym. Chem. Volume: 49 Issue: 14 Pages: 3020-3029
  • DOI: 10.1002/pola.24737
  • Peer Reviewed
• [Journal Article] Precision Synthesis of Poly (3-hexylthiophene) from Catalyst-Transfer Suzuki-Miyaura Coupling Polymerization (2011)
  • Author(s): Tsutomu Yokozawa
  • Journal Title: Macromol.Rapid Commun. Volume: 32 Issue: 11 Pages: 801-806
  • DOI: 10.1002/marc.201100037
  • Peer Reviewed
• [Journal Article] Efficient Low-Temperature Atom Transfer Radical Coupling and Its Application to Synthesis of Well- Defined Symmetrical Polybenzamides (2011)
  • Author(s): Chih-Feng Huang, Yoshihiro Ohta, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Macromolecules Volume: 44 Issue: 11 Pages: 4140-4148
  • DOI: 10.1021/ma200494m
  • Peer Reviewed
• [Journal Article] Chiral Amplification Based on Sergeants and Soldiers Effect in Helically Folded Poly(naphthalenecarboxamide) (2011)
  • Author(s): Koichiro Mikami, Hiroaki Daikuhara, Yuko Inagaki, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: Macromolecules Volume: 44 Issue: 9 Pages: 3185-3188
  • DOI: 10.1021/ma200055g
  • Peer Reviewed
• [Journal Article] Synthesis of a variety of star-shaped polybenzamides via chain-growth condensation polymerization with tetrafunctional porphyrin initiator (2011)
  • Author(s): Kazuo Yoshino, Akihiro Yokoyama, Tsutomu Yokozawa
  • Journal Title: J. Polym. Sci., Part A : Polym. Chem. Volume: 49 Issue: 4 Pages: 986-994
  • DOI: 10.1002/pola.24511
  • Peer Reviewed
• [Presentation] 芳香族ラダー型ポリアミド合成における反応条件の最適化 (2014)
  • Author(s): 倉持甚也,高石和人,横山明弘
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学東山キャンパス
• [Presentation] ビナフチルとビフェニルのねじれを利用した不斉空洞を有する大環状化合物の合成 (2014)
  • Author(s): 矢部達也,高石和人,横山明弘
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学東山キャンパス
• [Presentation] フェニルエステルモノマーを用いた芳香族ラダー型ポリアミドの合成 (2013)
  • Author(s): 倉持甚也,岸本一樹,高石和人,横山明弘
  • Organizer: 第62回高分子討論会
  • Place of Presentation: 金沢大学角間キャンパス
• [Presentation] 軸性不斉ビナフチルを用いた組井桁不斉化合物の合成 (2013)
  • Author(s): 矢部達也,高石和人,横山明弘
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 学習院大学目白キャンパス
• [Presentation] 不斉反転しない軸性不斉ビピリジルの合成と光学特性 (2013)
  • Author(s): 鈴木准,高石和人,横山明弘
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 学習院大学目白キャンパス
• [Presentation] 組井桁不斉を有するビナフトファンの合成 (2013)
  • Author(s): 矢部達也,高石和人,横山明弘
  • Organizer: 第10回ホスト・ゲスト化学シンポジウム
  • Place of Presentation: 和歌山大学
• [Presentation] 分子内不斉移動を利用した軸性不斉ビピリジルの合成とその構造 (2013)
  • Author(s): 鈴木准,高石和人,横山明弘
  • Organizer: 第10回ホスト・ゲスト化学シンポジウム
  • Place of Presentation: 和歌山大学