JP2003226691A - Bisbenzoxazole and method for producing the same - Google Patents
Bisbenzoxazole and method for producing the sameInfo
- Publication number
- JP2003226691A JP2003226691A JP2002024896A JP2002024896A JP2003226691A JP 2003226691 A JP2003226691 A JP 2003226691A JP 2002024896 A JP2002024896 A JP 2002024896A JP 2002024896 A JP2002024896 A JP 2002024896A JP 2003226691 A JP2003226691 A JP 2003226691A
- Authority
- JP
- Japan
- Prior art keywords
- bisbenzoxazole
- compound
- structural formula
- compound represented
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なビスベンゾ
オキサゾール化合物及びその製造方法に関するものであ
る。TECHNICAL FIELD The present invention relates to a novel bisbenzoxazole compound and a method for producing the same.
【０００2 】[000 2]
【従来の技術】ベンゾオキサゾール誘導体は、蛍光強度
が強いことや異なる特定波長において高い感度を持つこ
とから増感作用などの特性を有し、広範囲に利用が図ら
れている。例えば、フィルター用染料、色変換フィルタ
ー、カラー写真用感光材料、増感色素、蛍光増白剤、レ
ーザー色素、医療診断用蛍光薬剤、有機発光素子などの
利用の検討がなされている（特開２００１−２３４１５
９号公報、特開２００１−２２２０８６号公報、特開２
０００−２３９５４７号公報など）。このようなことか
ら、新規なベンゾオキサゾール誘導体及びその合成方法
の研究が積極的に進められている。従来知られているベ
ンゾオキサゾール誘導体化合物は、発する蛍光波長に関
し、顕著な媒体依存性を示す特性を有するものは少な
い。また、一般に、ベンゾオキサゾールを製造する際に
は、ｏ−アミノフエノールを低温で酸塩化物と反応させ
てｏ−ヒドロキシアミドに変換し、次に熱環化反応によ
る縮合反応を利用するものである。このように多段階工
程を経て目的性生物を製造するために、反応の制御は難
しく、反応収率も低い。 したがって、簡便に収率よく
製造する新たな合成方法の開発が必要とされている。2. Description of the Related Art Benzoxazole derivatives have properties such as sensitizing action because of their strong fluorescence intensity and high sensitivity at different specific wavelengths, and they are widely used. For example, the use of dyes for filters, color conversion filters, light-sensitive materials for color photography, sensitizing dyes, fluorescent whitening agents, laser dyes, fluorescent agents for medical diagnosis, organic light-emitting devices, etc. has been studied (Japanese Patent Laid-Open No. 2001-2001). -23415
No. 9, JP 2001-222860, JP 2
000-239547). For these reasons, research on new benzoxazole derivatives and methods for synthesizing them has been actively pursued. Most of the conventionally known benzoxazole derivative compounds have a property of exhibiting a remarkable medium dependence with respect to the emitted fluorescence wavelength. In general, when producing benzoxazole, o-aminophenol is reacted with an acid chloride at a low temperature to be converted into o-hydroxyamide, and then a condensation reaction by a thermal cyclization reaction is used. . As described above, since the target organism is produced through the multi-step process, it is difficult to control the reaction and the reaction yield is low. Therefore, there is a need for the development of a new synthetic method that can be simply and efficiently produced.
【０００３】[0003]
【発明が解決しようとする課題】本発明の課題は、発す
る蛍光波長に関し、顕著な蛍光変化を示す新規なベンゾ
オキサゾール誘導体化合物を提供するものである。ま
た、このベンゾオキサゾールを製造する際に、従来知ら
れているベンゾオキサゾール誘導体化合物の製造方法に
比較して、選択率が高く、安定に得られる方法を提供す
るものである。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel benzoxazole derivative compound which exhibits a remarkable change in fluorescence with respect to the emitted fluorescence wavelength. Further, the present invention provides a method for producing this benzoxazole, which has a high selectivity and can be stably obtained, as compared with a conventionally known method for producing a benzoxazole derivative compound.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、前記課題
について鋭意研究を進めた結果、以下の知見を得た。最
終目的生成物が含有する２つのベンゾオキサゾール化合
物の結合鎖の役割を果たすものであり、かつアミノフェ
ノ−ルの保護基として作用するイソブテニル基を、エー
テル結合として導入し、アミノ基が保護されている構造
式（２）で表される化合物を、安息香酸又はピリジンカ
ルボン酸のいずれかであるカルボン酸化合物と反応させ
て、酸アミド化合物である構造式（３）で表される化合
物とした後、１バッチでｏ−ヒドロキシアミドに変換
し、縮合反応を行い構造式（４）で表されるビスベンゾ
オキサゾール誘導体化合物を製造することができること
を見出した。構造式（２）で示される化合物は、最終的
には電子供与基として作用させることができるアミノ基
を種々の保護基を用いて製造されたものである。この保
護基の作用により、合成過程にある構造式２乃至４及び
目的生成物の精製も容易にすることができる。そして、
前記保護基を構造式（４）で示される化合物から外すこ
とにより、構造式（１）で示される新規なビスベンゾオ
キサゾールを得る事ができる。本発明で得られる新規な
構造式（１）で示されるビスベンゾオキサゾールは、こ
の化合物を溶解させる媒体に応じて発する蛍光色が変化
する特性を有しており、その特性を利用して適当な媒体
と組み合わせることにより蛍光色を変化させることがで
きるものである。Means for Solving the Problems As a result of intensive studies on the above problems, the present inventors have obtained the following findings. An amino group is protected by introducing an isobutenyl group, which plays a role of a bonding chain of two benzoxazole compounds contained in the final target product and acts as a protecting group of aminophenol, as an ether bond. After reacting the compound represented by Structural Formula (2) with a carboxylic acid compound which is either benzoic acid or pyridinecarboxylic acid to give a compound represented by Structural Formula (3) which is an acid amide compound, It was found that the bisbenzoxazole derivative compound represented by the structural formula (4) can be produced by converting into o-hydroxyamide in one batch and conducting a condensation reaction. The compound represented by the structural formula (2) is finally produced by using various protecting groups for an amino group which can act as an electron donating group. By the action of this protecting group, the purification of Structural Formulas 2 to 4 and the target product in the process of synthesis can be facilitated. And
By removing the protecting group from the compound represented by the structural formula (4), a novel bisbenzoxazole represented by the structural formula (1) can be obtained. The bisbenzoxazole represented by the novel structural formula (1) obtained in the present invention has a characteristic that the fluorescent color emitted changes depending on the medium in which this compound is dissolved, and it is suitable to utilize the characteristic. The fluorescent color can be changed by combining with a medium.
【０００５】本発明によると、以下の発明が提供され
る。
（１）一般式（Ｉ）で表されることを特徴とするビスベ
ンゾオキサゾール。According to the present invention, the following inventions are provided. (1) A bisbenzoxazole represented by the general formula (I).
【化３】（１）
（式中、Ｘは、ＣＨ又はＮを表す。）
（２）アミノ基が保護されている構造式（２）で表され
る化合物を、安息香酸又はピリジンカルボン酸と反応さ
せて、一般式（３）で示される酸アミド化合物を製造
し、続いて、１バッチ触媒反応により一般式（４）で示
される化合物へ変換後、脱保護して、構造式（１）で表
されるビスベンゾオキサゾール誘導体化合物を製造する
ことを特徴とするビスベンゾオキサゾール誘導体の製造
方法。[Chemical Formula 3] (1) (In the formula, X represents CH or N.) (2) A compound represented by the structural formula (2) in which an amino group is protected is reacted with benzoic acid or pyridinecarboxylic acid to give a compound represented by the general formula ( Bisbenzoxazole represented by the structural formula (1) is produced by producing the acid amide compound represented by 3), then converting it to the compound represented by the general formula (4) by one batch catalytic reaction, and deprotecting the compound. A method for producing a bisbenzoxazole derivative, which comprises producing a derivative compound.
【化４】 [Chemical 4]
【０００６】[0006]
【発明の実施の形態】本発明の目的物質は、構造式
（１）で表される化合物である。BEST MODE FOR CARRYING OUT THE INVENTION The target substance of the present invention is a compound represented by the structural formula (1).
【化５】（１） （式中、ＸはＣＨ又はＮを表す。）[Chemical formula 5] (1) (In the formula, X represents CH or N.)
【０００７】前記目的生成物の製法は、以下のとおりで
ある。
［１］原料物質には、最終目的生成物が含有する２つの
ベンゾオキサゾール化合物の結合鎖とアミノフエノ−ル
の保護基として作用するイソブテニル基を、エーテル結
合として導入した構造式（２）で表される化合物を用い
る。また、構造式（２）で示される化合物では、アミノ
基は保護されている。この保護基の作用により、以下の
合成過程で生成する構造式２乃至４の精製も容易にする
ことができるものである。The method for producing the target product is as follows. [1] The starting material is represented by the structural formula (2) in which an isobutenyl group acting as a protecting group for the aminophenol and a connecting chain of the two benzoxazole compounds contained in the final target product is introduced as an ether bond. Compound is used. Further, in the compound represented by the structural formula (2), the amino group is protected. By the action of this protecting group, the purification of Structural Formulas 2 to 4 produced in the following synthetic process can be facilitated.
【化６】（２） （式中、Ｒはアミノ基の保護基を表す。）[Chemical Formula 6] (2) (In the formula, R represents an amino-protecting group.)
【０００８】なお、前記構造式（２）で表される化合物
の製法は、以下のとおりである。４−アミノ−３−ニト
ロフエノールを溶媒中に溶解させ、無水フタル酸を添加
し、加熱条件下で反応させる。得られた前記ニトロ化合
物を還元して、４−イミジル−３−アミノフエノールを
製造する。次に、２−クロロメチル−１−プロペンを添
加して加熱条件下で反応させて、構造式（２）で示され
る原料化合物を得る事ができる。無水フタル酸と反応さ
せる溶媒には、トルエンなどの炭化水素系やDMF溶媒を
用い、８０から２００℃程度の範囲に加熱し、反応を促
進させるために無水条件下で行う。ニトロ化合物の還元
には、テトラヒドロフランなどの溶媒の存在下に、パラ
ジウムなどの水素添加触媒を活性炭などの担体に担持し
たものが用いられる。温度は、３０から２００℃程度の
温度が用いられる。The method for producing the compound represented by the structural formula (2) is as follows. 4-Amino-3-nitrophenol is dissolved in a solvent, phthalic anhydride is added, and the mixture is reacted under heating conditions. The obtained nitro compound is reduced to produce 4-imidyl-3-aminophenol. Next, 2-chloromethyl-1-propene can be added and reacted under heating conditions to obtain the raw material compound represented by the structural formula (2). As a solvent for reacting with phthalic anhydride, a hydrocarbon-based solvent such as toluene or a DMF solvent is used, heated to a range of about 80 to 200 ° C., and carried out under anhydrous conditions to accelerate the reaction. For the reduction of the nitro compound, a catalyst in which a hydrogenation catalyst such as palladium is supported on a carrier such as activated carbon in the presence of a solvent such as tetrahydrofuran is used. A temperature of about 30 to 200 ° C. is used.
【０００９】［２］前記構造式（２）で示される化合物
とカルボン酸化合物を、触媒の存在下に反応させて、酸
アミド化合物である構造式（３）で表される化合物を製
造する。カルボン酸化合物としては、安息香酸又はピリ
ジンカルボン酸が用いられる。反応には、ピリジンなど
塩基の存在下に、８０から１２０℃程度の範囲に加熱し
て触媒としてトリフェニルホスフィンを添加して行う。
反応終了後、食塩水溶液を添加して沈殿物をロ別して構
造式（３）で表される化合物を製造する。[2] The compound represented by the structural formula (2) is reacted with a carboxylic acid compound in the presence of a catalyst to produce an acid amide compound represented by the structural formula (3). Benzoic acid or pyridinecarboxylic acid is used as the carboxylic acid compound. The reaction is carried out in the presence of a base such as pyridine by heating to a range of about 80 to 120 ° C. and adding triphenylphosphine as a catalyst.
After completion of the reaction, a saline solution is added to separate the precipitate by filtration to produce the compound represented by the structural formula (3).
【化７】（３）
（式中、ＸはＣＨ又はＮを表し、Ｒはアミノ基の保護基
を表す。）[Chemical 7] (3) (In the formula, X represents CH or N, and R represents a protecting group for an amino group.)
【００１０】［３］酸アミド化合物である構造式（３）
で表されるアミド化合物を、触媒の存在下で熱反応によ
り、１バッチでｏ−ヒドロキシアミドに変換し、縮合反
応して構造式（４）で表されるビスベンゾオキサゾール
誘導体化合物を製造する。[3] Structural formula (3) which is an acid amide compound
The amide compound represented by the formula (4) is converted into o-hydroxyamide in one batch by thermal reaction in the presence of a catalyst and subjected to a condensation reaction to produce a bisbenzoxazole derivative compound represented by the structural formula (4).
【化８】（４）
（式中、ＸはＣＨ又はＮを表し、Ｒはアミノ基の保護基
を表す。）[Chemical 8] (4) (In the formula, X represents CH or N, and R represents a protecting group for an amino group.)
【００１１】［４］前記保護基を構造式（４）で示され
る化合物を加水分解し、脱保護することにより、目的物
質である構造式（１）で表される化合物を得ることがで
きる。[4] The compound represented by the structural formula (1), which is a target substance, can be obtained by hydrolyzing the protecting group with a compound represented by the structural formula (4) and deprotecting the compound.
【化９】（１） [Chemical 9] (1)
【００１２】本発明の構造式（１）で得られる化合物
は、溶媒の種類に応じて、発する蛍光の波長を変化させ
ることができる。例えば、クロロホルム中では青緑色、
また、ジメチルスルホオキシド中では赤色の発光を得る
事ができる。また、蛍光増白剤として利用することがで
きる。このような蛍光の発光波長を変化させることがで
きることにより、感熱、感光蛍光記録材料及び有機ＥＬ
デイスプレイの構成材料に利用することができる。ま
た、医療分野においては細胞の新規な蛍光プローブとし
て利用することができる。The compound obtained by the structural formula (1) of the present invention can change the wavelength of the emitted fluorescence depending on the kind of the solvent. For example, blue-green in chloroform,
In addition, red luminescence can be obtained in dimethyl sulfoxide. It can also be used as a fluorescent whitening agent. By being able to change the emission wavelength of such fluorescence, heat-sensitive, photosensitive fluorescent recording material and organic EL
It can be used as a constituent material of a display. In the medical field, it can be used as a novel fluorescent probe for cells.
【００１３】[0013]
【実施例】以下に本発明の内容を実施例によりさらに詳
細に説明する。しかしながら、本発明は以下の実施例に
より拘束されるものではない。
実施例１ （原料化合物の調製）
４−アミノ−２−ニトロフエノール１０．０ｇを、８０
ｍｌの脱水ＤＭＦに溶解させ、無水フタル酸９．６１ｇ
を添加して、十分に溶解させた後、８０℃で２時間窒素
雰囲気下に攪拌した。これに、６０ｍｌのトルエンを添
加し、オイルバス温度を１６０℃に上昇させて、さらに
２４時間脱水反応を継続した。反応終了後、室温になる
まで放冷し、結晶を析出させた。得られた結晶をロ別
し、メタノールで洗浄し、４−イミジルー３−ニトロフ
エノールを１７．７０ｇ（９６％収率）を得た。次に、
この化合物１０ｇを、パラジウム−黒触媒（パラジウム
１０％）１．２ｇを、ＴＨＦ３００ｍｌ中に加えて、１
気圧水素の存在下に、室温で３０時間反応させた。ＴＨ
Ｆ溶媒を減圧条件下に留去させて、４−イミジルー３−
アミノフエノール８．８６ｇ（９９％収率）を得た。こ
の化合物６．０ｇを、脱水ＤＭＦに溶解させ、０．５７
ｇの水酸化ナトリウムを添加して、窒素存在下に６０℃
で２時間攪拌した。その後室温に下げて３−クロロー２
−クロロメチル−１−プロペン１．４７ｇを添加して、
さらに２４時間７５℃で反応させた。その反応液にシリ
カゲル３５ｇを添加して、ＤＭＦを留去させて、クロロ
ホルムを溶出させたシリカゲルカラムを用いて、原料物
質である構造式（２）で示される化号物を６５％の収率
で得た。EXAMPLES The contents of the present invention will be described in more detail below with reference to examples. However, the present invention is not bound by the following examples. Example 1 (Preparation of raw material compound) 10.0 g of 4-amino-2-nitrophenol was added to 80
Dissolve in dehydrated DMF (9 ml) and add phthalic anhydride (9.61 g
Was added and dissolved sufficiently, and then stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. To this, 60 ml of toluene was added, the oil bath temperature was raised to 160 ° C., and the dehydration reaction was continued for another 24 hours. After completion of the reaction, the mixture was allowed to cool to room temperature to precipitate crystals. The obtained crystals were separated by filtration and washed with methanol to obtain 17.70 g (96% yield) of 4-imidiriu 3-nitrophenol. next,
To 10 g of this compound was added 1.2 g of palladium-black catalyst (10% of palladium) in 300 ml of THF to give 1
The reaction was carried out at room temperature for 30 hours in the presence of atmospheric pressure hydrogen. TH
The F solvent was distilled off under reduced pressure to give 4-imidiuru 3-
Obtained 8.86 g (99% yield) of aminophenol. This compound (6.0 g) was dissolved in dehydrated DMF to give 0.57.
g sodium hydroxide, 60 ° C in the presence of nitrogen
And stirred for 2 hours. After that, the temperature is lowered to room temperature and 3-chloro-2 is added.
1.47 g of -chloromethyl-1-propene was added,
The reaction was continued at 75 ° C. for 24 hours. 35 g of silica gel was added to the reaction solution, DMF was distilled off, and a silica gel column in which chloroform was eluted was used to obtain the compound represented by the structural formula (2) as a starting material in a yield of 65%. Got with.
【化１０】（２） [Chemical 10] (2)
【００１４】実施例２（構造式２で示される化合物より
構造式３で示される化合物の製造）
前記工程で得られた構造式（２）で示された化合物５．
０ｇと４−ピリジンカルボン酸２．２１ｇを、脱水ＮＭ
Ｐに溶解させ、次に、ピリジン６．２５ｍｌとトリフエ
ニルヒスフイン７ｇを添加し、（温度条件下に）３時間
反応させた。反応後、室温まで冷却し、１％食塩水１０
０ｍｌを添加し、生じた沈殿物をろ過による回収し、構
造式３で示される化合物 ５．２３ｇ（収率７６％）
を得た。Example 2 (Production of the compound represented by the structural formula 3 from the compound represented by the structural formula 2) The compound represented by the structural formula (2) obtained in the above step.
0 g and 4-pyridinecarboxylic acid 2.21 g were added to dehydrated NM
It was dissolved in P, and then 6.25 ml of pyridine and 7 g of triphenyl hisphine were added and reacted for 3 hours (under temperature condition). After the reaction, it was cooled to room temperature and 1% saline solution 10
0 ml was added, the resulting precipitate was collected by filtration, and 5.23 g of the compound represented by the structural formula 3 (yield 76%)
Got
【化１１】（３） [Chemical formula 11] (3)
【００１５】実施例３（構造式３で示される化合物より
構造式４で示される化合物の製造）
構造式３で示される化合物１ｇとＰＰＳＥ２ｇ、ｏ−ジ
クロロベンゼン／ＮＭＰ（１対１）の混合溶液２００ｍ
ｌを添加して、アルゴン存在下に１５５℃で５０時間、
加熱処理を行った。その後、溶媒を留去し、メタノール
で洗浄後、乾燥させ、構造式（４）で表される化合物
０．４７ｇ（収率９２％）を得た。Example 3 (Production of the compound represented by the structural formula 4 from the compound represented by the structural formula 3) A mixed solution of the compound 1g represented by the structural formula 3, PPSE 2g, and o-dichlorobenzene / NMP (1: 1). 200 m
1 for 50 hours at 155 ° C. in the presence of argon,
Heat treatment was performed. Then, the solvent is distilled off, washed with methanol, and then dried to obtain a compound represented by the structural formula (4).
0.47 g (yield 92%) was obtained.
【化１２】（４） [Chemical 12] (4)
【００１６】実施例４
構造式４で示される化合物１．０ｇを２００ｍｌのＴＨ
Ｆと４０ｍｌのエタノールの混合液に溶解させて、０．
２ｇのヒドラジン１水和物を加えて、窒素下で２４時間
還流させた。その後溶媒を留去し、カラム精製後７２％
の収率で構造式（１）で表される化合物を得た。Example 4 1.0 g of the compound represented by Structural Formula 4 was added to 200 ml of TH
It was dissolved in a mixed solution of F and 40 ml of ethanol,
2 g of hydrazine monohydrate was added and refluxed under nitrogen for 24 hours. After that, the solvent was distilled off and 72% after column purification
A compound represented by the structural formula (1) was obtained with a yield of.
【化１３】（１）
確認データ
実施例４で得られた（１）のＮＭＲデータ1
H NMR (CDCl3): δ 3.50 (s, 4H, -CH2-O-), 3.67 (b
s, 4H, -NH2), 5.05 (s,2H, CH2=C), 6.52 (d, J = 2.
1, 2H, Ar), 6.83 (d, J = 2.15, 2H, Ar), 7.67(d, J
= 6.1, 4H, Ar), 8.60 (dd, J = 1.7, 2.9, 4H, Ar);
13C NMR (CDCl3):δ 159.47, 149.47, 143.41, 143.25,
142.91, 141.57, 133.19, 122.14, 119.52, 114.53, 1
14.06, 102.21, 34.89.[Chemical 13] (1) Confirmation data NMR data of (1) obtained in Example 4 1 H NMR (CDCl 3 ): δ 3.50 (s, 4H, —CH 2 —O—), 3.67 (b
s, 4H, -NH 2 ), 5.05 (s, 2H, CH 2 = C), 6.52 (d, J = 2.
1, 2H, Ar), 6.83 (d, J = 2.15, 2H, Ar), 7.67 (d, J
= 6.1, 4H, Ar), 8.60 (dd, J = 1.7, 2.9, 4H, Ar);
13 C NMR (CDCl 3 ): δ 159.47, 149.47, 143.41, 143.25,
142.91, 141.57, 133.19, 122.14, 119.52, 114.53, 1
14.06, 102.21, 34.89.
【００１７】実施例５
実施例４で得られた１の異なる溶媒中での蛍光ピーク波
長（励起波長２９０nm）
クロロホルム中 λmax= ５１９nm ＤＭＳＯ中 λ
max= ５８１nmExample 5 Fluorescence peak wavelength (excitation wavelength 290 nm) in one different solvent obtained in Example 4 in chloroform λmax = 519 nm λ in DMSO
max = 581nm
【００１８】[0018]
【発明の効果】本発明によれば、新規なベンゾオキサゾ
ール誘導体化合物及びベンゾオキサゾール誘導体の新規
な製造方法が得られる。この新規な化合物の発する蛍光
は、溶解させる溶媒の種類によって変化する。この特性
を利用して外部刺激によって溶媒の極性を制御すること
により、情報記録材料や有機ＥＬデイスプレイ材料とし
て利用することができる。また媒体の極性に敏感なこと
から細胞内の局所的な極性環境を調べることができる新
規な蛍光プローブとして利用することができる。According to the present invention, a novel benzoxazole derivative compound and a novel method for producing a benzoxazole derivative can be obtained. The fluorescence emitted by this novel compound changes depending on the type of solvent to be dissolved. By controlling the polarity of the solvent by an external stimulus utilizing this characteristic, it can be used as an information recording material or an organic EL display material. Further, since it is sensitive to the polarity of the medium, it can be used as a novel fluorescent probe capable of examining the local polar environment in cells.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 平谷 和久 茨城県つくば市東１−１−１ 独立行政法 人産業技術総合研究所つくばセンター内 Ｆターム(参考） 4C056 AA01 AB01 AC02 AD02 AE03 AF01 FA04 FB01 FC01 4C063 AA05 CC12 CC52 DD04 DD12 EE05 EE10 4C204 AB02 BB04 CB04 DB30 EB03 FB17 GB01 ─────────────────────────────────────────────────── ─── Continued front page (72) Inventor Kazuhisa Hiratani 1-1-1 Higashi 1-1-1 Tsukuba City, Ibaraki Prefecture Inside the Tsukuba Center, National Institute of Advanced Industrial Science and Technology F-term (reference) 4C056 AA01 AB01 AC02 AD02 AE03 AF01 FA04 FB01 FC01 4C063 AA05 CC12 CC52 DD04 DD12 EE05 EE10 4C204 AB02 BB04 CB04 DB30 EB03 FB17 GB01
Claims (2)
ビスベンゾオキサゾール。 【化１】（１） （式中、Ｘは、ＣＨ又はＮを表す。）1. A bisbenzoxazole represented by the general formula (I). [Chemical formula 1] (1) (In the formula, X represents CH or N.)
表される化合物を、安息香酸又はピリジンカルボン酸と
反応させて、一般式（３）で示される酸アミド化合物を
製造し、続いてｏ−ヒドロキシアミド体の生成、縮合反
応を経て製造される一般式（４）で示されるビスベンゾ
オキサゾール誘導体を脱保護により構造式（１）で表さ
れるビスベンゾオキサゾール誘導体を製造することを特
徴とするビスベンゾオキサゾール誘導体の製造方法。 【化２】 2. A compound represented by the structural formula (2) in which an amino group is protected is reacted with benzoic acid or pyridinecarboxylic acid to produce an acid amide compound represented by the general formula (3), Then, a bisbenzoxazole derivative represented by the structural formula (1) is produced by deprotecting the bisbenzoxazole derivative represented by the general formula (4), which is produced through generation and condensation reaction of an o-hydroxyamide compound. A method for producing a bisbenzoxazole derivative, comprising: [Chemical 2]
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106198476A (en) * | 2016-07-29 | 2016-12-07 | 贵州大学 | A kind of to Mg2+and Ga3+there is reagent and the recognition methods thereof of high Selective recognition function |
| EP3466925A4 (en) * | 2016-06-03 | 2019-11-13 | DIC Corporation | Substituted or unsubstituted allyl group-containing maleimide compound, production method therefor, and composition and cured product using said compound |
| CN112174946A (en) * | 2020-11-05 | 2021-01-05 | 四川大学华西医院 | Lipid drop fluorescent probe and synthetic method and application thereof |
-
2002
- 2002-02-01 JP JP2002024896A patent/JP3975263B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3466925A4 (en) * | 2016-06-03 | 2019-11-13 | DIC Corporation | Substituted or unsubstituted allyl group-containing maleimide compound, production method therefor, and composition and cured product using said compound |
| US10981865B2 (en) | 2016-06-03 | 2021-04-20 | Dic Corporation | Substituted or unsubstituted allyl group-containing maleimide compound, production method therefor, and composition and cured product using said compound |
| CN106198476A (en) * | 2016-07-29 | 2016-12-07 | 贵州大学 | A kind of to Mg2+and Ga3+there is reagent and the recognition methods thereof of high Selective recognition function |
| CN112174946A (en) * | 2020-11-05 | 2021-01-05 | 四川大学华西医院 | Lipid drop fluorescent probe and synthetic method and application thereof |
| CN112174946B (en) * | 2020-11-05 | 2023-03-21 | 四川大学华西医院 | Lipid drop fluorescent probe and synthetic method and application thereof |
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