Preparations of novel selenium- or tellurium-containing heterocycles and their functionalities

• Project/Area Number: 19590022
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Hokuriku University
• Principal Investigator: SASHIDA Haruki Hokuriku University, 薬学部, 教授 (70102746)
• Co-Investigator(Kenkyū-buntansha): SUZUKI Hirokazu 北陸大学, 薬学部, 助教 (70257484)
• Project Period (FY): 2007 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2009: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2008: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2007: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: ヘテロ環化学 / イソテルロクロメン / 1-ベンゾテルロピリリウム塩 / イソセレノシアネート / 5-exo-dig / 6-endo-dig / カルコゲノール / 分子内環化 / 三重結合 / セレノラクトン / 分子内三重結合 / タンデム環化 / 1-ベンゾセレノピリリウム塩 / 1-Benzotelluropyrylium Salt / 1-Benzoselenopyrylium Salt / タンデム環化付加

Research Abstract

Preparations of novel several selenium- or tellurium- containing heterocycles by the intramolecular cyclization of the selenols, tellurols and related compounds to a triple bond are achieved. The structures, reactivities and functionalities involving the bioactivities of the obtained products were also examined towards the medicinal chemistry.

Research Products

• [Journal Article] A facile and practical solvent-free one-pot synthesis of (Z)-4-methylidene-3-selenaquinoline derivatives from o-ethynylanilines and isoselenocyanates (2010)
  • Author(s): Haruki Sashida, Chao Pan, Mamoru Kaname, Mao Minoura
  • Journal Title: Synthesis (in press)
  • Peer Reviewed
• [Journal Article] A straightforward double intramolecular cyclization of dibenzyl dichalcogenols into a triple bond (2010)
  • Author(s): Haruki Sashida, Mamoru Kaname, Akemi Nakayama, Hirokazu Suzuki, Mao Minoura
  • Journal Title: Tetrahedron 66 Pages: 5149-5157
  • Peer Reviewed
• [Journal Article] Tin-tellurium exchange reaction in tin-containing heterocycles: A new entry for the preparation of tellurium heterocycles (2010)
  • Author(s): Haruki Sashida, Mamoru Kaname, Kazuo Ohyanagi
  • Journal Title: Heterocycles 82(in press)
  • NAID: 40017418844
  • Peer Reviewed
• [Journal Article] Novel oxidative ring opening reaction of isotellurochromones to bis(o-formylstylyl) ditellurides (2010)
  • Author(s): Haruki Sashida, Hirohito Satoh, Kazuo Ohyanagi, Mamoru Kaname
  • Journal Title: Molecules 15 Pages: 1466-1472
  • Peer Reviewed
• [Journal Article] 2-Substituted isotellurochromenium salt derivatives: preparations, structures and spectroscopic properties (2010)
  • Author(s): Haruki Sashida, Shoko Nakabayashi, Mamoru Kaname, Mao Minoura
  • Journal Title: Heterocycles 80 Pages: 1339-1352
  • NAID: 40016991497
  • Peer Reviewed
• [Journal Article] Neuritogenic activities of 1-alkyloxygenipins (2010)
  • Author(s): Hirokazu Suzuki, et al.
  • Journal Title: Chem.Pharm.Bull. 58 Pages: 168-171
  • NAID: 120006378598
  • Peer Reviewed
• [Journal Article] 2-Substituted isotellurochromenium salt derivatives : preparations, structures and spectroscopic properties (2010)
  • Author(s): Haruki Sashida, Shoko Nakabayashi, Mamoru Kaname, Mao Minoura
  • Journal Title: Heterocycles 80 Pages: 1339-1352
  • NAID: 40016991497
  • Peer Reviewed
• [Journal Article] Novel oxidative ring opening reaction of 1H-isotellurochromones to bis(o-formylstyryl)ditellurides (2010)
  • Author(s): Haruki Sashida, Hirohito Satoh, Kazuo Ohyanagi, Mamoru Kaname
  • Journal Title: Molecules 15 Pages: 1466-1472
  • Peer Reviewed
• [Journal Article] 1-ベンゾテルロピリリウム塩の化学:合成, 構造, 反応 (2009)
  • Author(s): 指田春喜, 箕浦真生
  • Journal Title: 有機合成化学協会誌 67 Pages: 714-723
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of N, N'-diacyl hexahydropyridazines (2009)
  • Author(s): Mamoru Kaname, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Heterocycles 79 Pages: 647-658
  • Peer Reviewed
• [Journal Article] An alternative convenient synthesis of piperidazine-3-carboxylic acid derivatives (2009)
  • Author(s): Mamoru Kaname, Masae Yamada, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Chem. Pharm. Bull. 57 Pages: 49-54
  • NAID: 110007021620
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of N,N'-diBoc-hexahydropyridazines (2009)
  • Author(s): Mamoru Kaname, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Heterocycles 79 Pages: 647-658
  • NAID: 40016543096
  • Peer Reviewed
• [Journal Article] 1-ベンゾテルロピリリウム塩の化学:合成,構造および反応 (2009)
  • Author(s): 指田春喜, 箕浦真生
  • Journal Title: 有機合成化学協会誌 67 Pages: 714-723
  • NAID: 10025399312
  • Peer Reviewed
• [Journal Article] An alternative convenient synthesis of piperidazine-3-carboxylic acidderivatives (2009)
  • Author(s): Mamoru Kaname
  • Journal Title: Chem. Pharm. Bull. 57 Pages: 49-54
  • Peer Reviewed
• [Journal Article] An efficient one-pot synthetic method for selenium-containing medium-sized α,β-unsaturated cyclic ketones (2008)
  • Author(s): Haruki Sashida, Akemi Nakayama, Mamoru Kaname
  • Journal Title: Synthesis Pages: 3229-3236
  • Peer Reviewed
• [Journal Article] An efficient transformation of cyclic ene-carbamates into ω-(N-formylamino)carboxylic acids by ruthenium tetroxide oxidation (2008)
  • Author(s): Mamoru Kaname, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Chem. Pharm. Bull. 56 Pages: 1310-1313
  • NAID: 110006878904
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of α-(N-acyl)aminophosphonic acid diesters (2008)
  • Author(s): Mamoru Kaname, Hironori Mashige, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Heterocycles 76 Pages: 429-438
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids (2008)
  • Author(s): Mamoru Kaname, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Tetrahedron Lett. 49 Pages: 2786-2788
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of α-(N-acyl)aminophosphonic aciddiesters (2008)
  • Author(s): Kaname Mamoru
  • Journal Title: Heterocycles 76 Pages: 429-438
  • Peer Reviewed
• [Journal Article] An efficient transformation of cyclic ene-carbamates into ω-(N-formylamino)carboxylic acids by ruthenium tetroxide oxidation (2008)
  • Author(s): Kaname Mamoru
  • Journal Title: Chem. Pharm. Bull. 56 Pages: 1310-1313
  • Peer Reviewed
• [Journal Article] An efficient One-Pot Synthetic Method for Selenium-Containing Medium-Sized α, β-Unsaturated Cyclic Ketones (2008)
  • Author(s): Haruki Sashida
  • Journal Title: Synthesis Pages: 3229-3236
  • Peer Reviewed
• [Journal Article] Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids (2008)
  • Author(s): Mamoru Kaname, Shigeyuki Yoshifuji, Haruki Sashida
  • Journal Title: Tetrahedron Letters 49 Pages: 2786-2788
  • Peer Reviewed
• [Journal Article] 1-Benzoselenopyrylium salts and 1-benzotelluropyrylium salts: Preparations, structures and reactions (2007)
  • Author(s): Haruki Sashida
  • Journal Title: Mini Reviews in Organic Chemistry 4 Pages: 105-114
  • Peer Reviewed
• [Journal Article] 1-Benzoselenopyrylium Salts and 1-Benzotelluropyrylium Salts: Preparation, Structures and Reactions (2007)
  • Author(s): Haruki Sashida
  • Journal Title: Mini-Reviews in Organic Chemistry 4 Pages: 105-114
  • Peer Reviewed
• [Presentation] 酸触媒によるσ-エチニルフェノール類とイソセレノシアネートとの付加・環化反応 (2010)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] 酸触媒によるo-エチニルフェノール類とイソセレノシアネートとの付加・環化反応 (2010)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] 三重結合を有するアルコールおよびフェノール類とイソセレノシアネート類との付加・環化反応 (2009)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 北陸支部120回例会
  • Place of Presentation: 金沢
  • Year and Date: 2009-07-11
• [Presentation] 三重結合を有するアルコールおよびフェノール類とイソセレノシアネート類との付加・環化反応 (2009)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 日本薬学会北陸支部第120例会
  • Place of Presentation: 金沢
  • Year and Date: 2009-07-11
• [Presentation] イソテルロクメニウム塩関連化合物:合成, 構造, 性質 (2009)
  • Author(s): 要衛, 中林祥子, 指田春喜
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
• [Presentation] σ-エチニルアニリンおよびフェノール類とイソセレノシアネートとの付加・環化反応 (2009)
  • Author(s): 要衛, 潘超, 山田理恵, 村山次哉, 指田春喜
  • Organizer: 第39回複素環化学討論会
  • Place of Presentation: 柏
• [Presentation] Double intramolecular 5-exo and 6-endo cyclization of dibenzyl ditellurols into triple bond (2009)
  • Author(s): Haruki Sashida, Mamoru Kaname, Akemi Nakayama, Mao Minoura
  • Organizer: 13th Blue Danube Symposium on Heterocyclic Chemistry
  • Place of Presentation: Bled, Slovenia
• [Presentation] Selenium-containing heterocycles 2. A straightforward double intramolecular cyclization of dibenzyl diselenols into an ethynyl group (2009)
  • Author(s): Haruki Sashida, Akemi Nakayama, Mamoru Kaname
  • Organizer: 22nd International Congress on Heterocyclic Chemistry
  • Place of Presentation: St. John's, Canada
• [Presentation] Selenium-containing heterocycles 1. One-pot synthesis of (Z)-1-methylidenebenzo[c]selenophenes from o-ethynylbomobenzenes and isoselenocyanate (2009)
  • Author(s): Mamoru Kaname, Haruki Sashida
  • Organizer: 22nd International Congress on Heterocyclic Chemistry
  • Place of Presentation: St. John's, Canada
• [Presentation] セレノール類の三重結合への環化反応(1):ヨードサイクリゼーションによるベンゾ[c]セレノフェン誘導体の合成 (2009)
  • Author(s): 要衛, 指田春喜
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] セレノール類の三重結合への環化反応(2):マイクロウェーブ照射による3-セレナキノリン類の効率的合成 (2009)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] Selenium-containing heterocycles 1. One-pot synthesis of(Z)-1-methylidenebenzo[c]selenophenes from o-ethynylbromobenzenes and isoselenocyanate (2009)
  • Author(s): Mamoru Kaname, Haruki Sashida
  • Organizer: 22^<th> International Congress on Heterocyclic Chemistry
  • Place of Presentation: St.John's, Canada
• [Presentation] Selenium-containing heterocycles 2. A straightforward double intramolecular cyclization of dibenzyl diselenides into a ethynyl group (2009)
  • Author(s): Haruki Sashida, Akemi Nakayama, Mamoru Kaname
  • Organizer: 22^<th> International Congress on Heterocyclic Chemistry
  • Place of Presentation: St.John's, Canada
• [Presentation] Double intramolecular 5-exo and 6-endo cyclization of dibenzyl ditellurols into a triple bond (2009)
  • Author(s): Haruki Sashida, Mamoru Kaname, Akemi Nakayama, Mao Minoura
  • Organizer: 13^<th> Blue Danube Symposium on Heterocyclic Chemistry
  • Place of Presentation: Bled, Slovenia
• [Presentation] o-エチニルアニリンおよびフェノール類とイソセレノシアネートとの付加・環化反応 (2009)
  • Author(s): 要衛, 潘超, 山田理英, 村山次哉, 指田春喜
  • Organizer: 第39回複素環化学討論会
  • Place of Presentation: 柏
• [Presentation] イソテルロクメニウム塩関連化合物:合成,構造,性質 (2009)
  • Author(s): 要衛, 中林祥子, 指田春喜
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
• [Presentation] セレノール類の分子内三重結合への環化反応(1) : ヨードサイクリゼーションによるベンソ[с]セレノフェン誘導体の合成 (2009)
  • Author(s): 要 衛
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] セレノール類の分子内三重結合への環化反応(2) : マイクロウェーブ照射による3-セレナキノリン類の効率的合成 (2009)
  • Author(s): 潘 超
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] o-エチニルアニリン類とイソセレノシアネートによる3-セレナキノリン誘導体の合成 (2008)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 日本薬学会北陸支部第119回例会
  • Place of Presentation: 金沢
  • Year and Date: 2008-11-09
• [Presentation] ビス(σ-エチニルベンジルカルコゲノール)関連化合物の環化反応 (2008)
  • Author(s): 要衛, 中山明美, 指田春喜
  • Organizer: 日本薬学会北陸支部第119回例会
  • Place of Presentation: 金沢
  • Year and Date: 2008-11-09
• [Presentation] ο-エチニルアニリン類とイソセレノシアネートによる3-セレナキノリン誘導体の合成 (2008)
  • Author(s): 潘 超
  • Organizer: 日本薬学会北陸支部第119回例会
  • Place of Presentation: 金沢
  • Year and Date: 2008-11-09
• [Presentation] ビス(ο-エチニルペンジルカルコゲノール)関連化合物の環化反応 (2008)
  • Author(s): 中山 明美
  • Organizer: 日本薬学会北陸支部第119回例会
  • Place of Presentation: 金沢
  • Year and Date: 2008-11-09
• [Presentation] σ-エチニルフェニルリチウムとイソセレノシアネートによる含セレン複素環合成 (2008)
  • Author(s): 要衛, 指田春喜
  • Organizer: 日本薬学会北陸支部第118回例会
  • Place of Presentation: 富山
  • Year and Date: 2008-07-05
• [Presentation] ο-エチニルフェニルリチウムとイソセレノシアネートによる含セレン複素環合成 (2008)
  • Author(s): 要 衛
  • Organizer: 日本薬学会北陸支部第118回例会
  • Place of Presentation: 富山
  • Year and Date: 2008-07-05
• [Presentation] A new one-pot synthetic method for selenium-containing medium-sized α,β-unsaturated cyclic ketones by the ring-expansion reaction of selenolavtones with ethynyllithium (2008)
  • Author(s): Haruki Sashida, Akemi Nakayama, Mamoru Kaname
  • Organizer: 23th European colloqium on heterocyclic chemistry
  • Place of Presentation: Antwerp, Belgium
• [Presentation] 三重結合を有する求核剤とイソセレノシアネートとの反応による含セレン複素環合成 (2008)
  • Author(s): 要衛, 潘超, 指田春喜
  • Organizer: 第38回複素環化学討論会
  • Place of Presentation: 福山
• [Presentation] 各種σ-エチニルベンジルカルコゲノール類の環化反応 (2008)
  • Author(s): 要衛, 中山明美, 指田春喜
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
• [Presentation] 分子内三重結合へのジカルコゲノールの位置選択的タンデム環化反応 (2008)
  • Author(s): 要衛, 中山明美, 指田春喜
  • Organizer: 日本薬学会第128回年会
  • Place of Presentation: 横浜
• [Presentation] 各種ο-エチニルペンジルカルコゲノール類の環化反応 (2008)
  • Author(s): 中山 明美
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
• [Presentation] A new one-pot synthetic method for selenium-containing medium-sizedα, β-unsaturated cyclic ketones by the ring-expansion reaction of selenolavtones with ethynyllithium (2008)
  • Author(s): Haruki Sashida
  • Organizer: 23th European colloqium on heterocyclic chemistry
  • Place of Presentation: Antwerp, Belgium
• [Presentation] 分子内三重結合へのジカルコゲノールの位置選択的タンデム環化反応 (2008)
  • Author(s): 要 衛, 中山 明美, 指田 春喜
  • Organizer: 日本薬学会第128年会
  • Place of Presentation: パシフィコ横浜
• [Presentation] 四酸化ルテニウム酸化(単層法)を用いる環状N-アシルアミン類からω-アミノ酸への変換 (2007)
  • Author(s): 要衛, 吉藤茂行, 指田春喜
  • Organizer: 第33回反応と合成のシンポシンポジウム
  • Place of Presentation: 長崎
• [Presentation] セレノラクトン類のエチニルリチウムによる環拡大反応:含セレンα,β-不飽和中員環ケトンの生成 (2007)
  • Author(s): 要衛, 中山明美, 指田春喜
  • Organizer: 第37回複素環化学討論会
  • Place of Presentation: 長野
• [Presentation] [4+2^+] Polar cycloaddition of 2-benzotelluropyrylium salts and reaction of the cycloadducts with nucleophiles (2007)
  • Author(s): Haruki Sashida, Kazuo Ohyanagi
  • Organizer: 10th International Conference on the Chemistry of Selenium and Tellurium
  • Place of Presentation: Lodz, Poland
• [Presentation] Introduction of carbon functional groups into C-1 position of 2-benzotelluropyrylium salts (2007)
  • Author(s): Haruki Sashida, Kazuo Ohyanagi
  • Organizer: 10th International Conference on Pure and Applied Heterocyclic Chemistry
  • Place of Presentation: Luxor, Egypt
• [Presentation] [4+2^+]Polar cycloaddition of 2-benzotelluropyrylium Salts and reaction of the cycloadducts with nucleophiles (2007)
  • Author(s): Haruki Sashida
  • Organizer: 10th International Conference on the Chemistry of Selenium and tellurium
  • Place of Presentation: Poland, Lodz
• [Presentation] セレノラクトン類のエチニルリチウムによる環拡大反応:含セレンα,β-不飽和中員環ケトンの生成 (2007)
  • Author(s): 要 衛, 中山 明美, 指田 春喜
  • Organizer: 第37回複素環化学討論会
  • Place of Presentation: 長野市若里市民文化ホール
• [Presentation] 四酸化ルテニウム酸化(単層法)を用いる環状N-アシルアミンからω-アミノ酸への変換 (2007)
  • Author(s): 要 衛, 吉藤 茂行, 指田 春喜
  • Organizer: 第32回反応と合成の進歩シンポジウム
  • Place of Presentation: 長崎市長崎ブリックホール
• [Patent(Industrial Property Rights)] 含セレン複素環化合物及びその用途 (2009)
  • Inventor(s): 指田春喜, 要衛
  • Industrial Property Rights Holder: 指田春喜, 要衛
  • Filing Date: 2009-04-21
  • Acquisition Date: 2009-04-21
• [Patent(Industrial Property Rights)] 含セレン複素環化合物及びその用途 (2009)
  • Inventor(s): 指田春喜, 要衛
  • Industrial Property Rights Holder: 指田春喜, 要衛
  • Filing Date: 2009-04-21