JPS645595B2 - - Google Patents
Info
- Publication number
- JPS645595B2 JPS645595B2 JP18689281A JP18689281A JPS645595B2 JP S645595 B2 JPS645595 B2 JP S645595B2 JP 18689281 A JP18689281 A JP 18689281A JP 18689281 A JP18689281 A JP 18689281A JP S645595 B2 JPS645595 B2 JP S645595B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- ethoxycarbonyl
- carbon atoms
- substituted
- aminomaleimide
- 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.)
- Expired
Links
- -1 N-substituted aminomaleimide Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- FUQHJLWTRNTWRC-UHFFFAOYSA-N (2,5-dioxopyrrol-3-yl)urea Chemical compound NC(=O)NC1=CC(=O)NC1=O FUQHJLWTRNTWRC-UHFFFAOYSA-N 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- TUZVMPXGFZSNBG-UHFFFAOYSA-N 3-aminopyrrole-2,5-dione Chemical compound NC1=CC(=O)NC1=O TUZVMPXGFZSNBG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
この発明は新規化合物であるＮ−置換アミノマ
レイミド類の製法に関する。さらに詳しくは、こ
の発明は、
式
（式中、R1は炭素数１〜４のアルキル基または
ハロゲン原子を示し、R2は核の水素原子が炭素
数１〜４のアルキル基またはアルコキシ基で置換
されたフエニル基を示し、R3は炭素数２〜５の
アルコキシカルボニル基を示す。）で表わされる
カルバモイルアミノマレイミド類と第３アミンと
を反応させることを特徴とする
式
（式中、R1、R2およびR3は、それぞれ、前記と
同一の意味を有する。）で表わされるＮ−置換ア
ミノマレイミド類の製法である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for preparing new compounds, N-substituted aminomaleimides. More specifically, the invention provides the formula (In the formula, R 1 represents an alkyl group having 1 to 4 carbon atoms or a halogen atom, R 2 represents a phenyl group in which the hydrogen atom in the nucleus is substituted with an alkyl group or an alkoxy group having 1 to 4 carbon atoms, and R 3 represents an alkoxycarbonyl group having 2 to 5 carbon atoms.) A formula characterized by reacting a carbamoylaminomaleimide represented by the formula (3 represents an alkoxycarbonyl group having 2 to 5 carbon atoms) with a tertiary amine. (In the formula, R 1 , R 2 and R 3 each have the same meaning as above.) This is a method for producing an N-substituted aminomaleimide.
式〔〕で表わされるＮ−置換アミノマレイミ
ド類は農薬、医薬、さらにはこれらの中間体とし
て有用である。 N-substituted aminomaleimides represented by the formula [] are useful as agricultural chemicals, medicines, and intermediates thereof.
特に、イネ白葉枯病およびキユウリうどん粉病
に対する農園芸用殺菌剤として有用である。 It is particularly useful as an agricultural and horticultural fungicide against rice blight and cucumber powdery mildew.
式〔〕で表わされるカルバモイルアミノマレ
イミド類は、
式
（式中、R1およびR3は前記と同一の意味を有す
る。）で表わされるアミノマレイミド類とホスゲ
ンまたはクロロギ酸トリクロロメチルエステルと
を、ピリジンの存在下で反応させ、ついで反応生
成物を
式
R2NH2 〔〕
（式中、R2は前記と同一の意味を有する。）で表
わされるアミノ類と反応させる方法（本特許出願
人の出願に係る特願昭56−160985号）で合成する
ことができる。カルバモイルアミノマレイミド類
の具体例としては、１−クロロフエニル−３−エ
トキシカルボニル−４−（トリルカルバモイル）
アミノマレイミド、１−ブロモフエニル−３−エ
トキシカルボニル−４−（トリルカルバモイル）
アミノマレイミド、１−クロロフエニル−３−エ
トキシカルボニル−４−（メトキシフエニルカル
バモイル）アミノマレイミド、３−エトキシカル
ボニル−４−（メトキシフエニルカルバモイル）
アミノ−１−トリルマレイミド、３−エトキシカ
ルボニル−１−トリル−４−（トリルカルバモイ
ル）アミノマレイミド、１−クロロフエニル−３
−メトキシカルボニル−４−（トリルカルバモイ
ル）アミノマレイミド、３−メトキシカルボニル
−４−（メトキシフエニルカルバモイル）アミノ
−１−（トリル）マレイミドなどが挙げられる。 The carbamoylaminomaleimide represented by the formula [] is the formula (wherein R 1 and R 3 have the same meanings as above) and phosgene or chloroformic acid trichloromethyl ester are reacted in the presence of pyridine, and then the reaction product is expressed by the formula Synthesized by a method of reacting with an amino compound represented by R 2 NH 2 [] (in the formula, R 2 has the same meaning as above) (Japanese Patent Application No. 160985, filed by the applicant of this patent) can do. Specific examples of carbamoylaminomaleimides include 1-chlorophenyl-3-ethoxycarbonyl-4-(tolylcarbamoyl)
Aminomaleimide, 1-bromophenyl-3-ethoxycarbonyl-4-(tolylcarbamoyl)
Aminomaleimide, 1-chlorophenyl-3-ethoxycarbonyl-4-(methoxyphenylcarbamoyl)aminomaleimide, 3-ethoxycarbonyl-4-(methoxyphenylcarbamoyl)
Amino-1-tolylmaleimide, 3-ethoxycarbonyl-1-tolyl-4-(tolylcarbamoyl)aminomaleimide, 1-chlorophenyl-3
-methoxycarbonyl-4-(tolylcarbamoyl)aminomaleimide, 3-methoxycarbonyl-4-(methoxyphenylcarbamoyl)amino-1-(tolyl)maleimide, and the like.
第３アミンの具体例としては、トリメチルアミ
ン、トリルエチルアミン、トリプロピルアミン、
トリブチルアミンなどの脂肪族第３アミンが好適
に使用される。 Specific examples of tertiary amines include trimethylamine, tolylethylamine, tripropylamine,
Aliphatic tertiary amines such as tributylamine are preferably used.
反応は不活性有機溶媒、たとえばベンゼン、ト
ルエン、クロロベンゼン、ジクロロベンゼンなど
の芳香族炭化水素、塩化メチレン、クロロホル
ム、四塩化炭素、塩化エチレンなどのハロゲン化
炭化水素の存在下に行なわれる。 The reaction is carried out in the presence of an inert organic solvent, such as an aromatic hydrocarbon such as benzene, toluene, chlorobenzene, dichlorobenzene, or a halogenated hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride, ethylene chloride.
反応方法としては、実質的に無水の条件下に、
カルバモイルアミノマレイミド類と第３アミンと
を接触させることができれば、いかなる方法でも
よい。 As a reaction method, under substantially anhydrous conditions,
Any method may be used as long as the carbamoylaminomaleimide and the tertiary amine can be brought into contact.
第３アミンの使用量は、カルバモイルアミノマ
レイミド類１モル当たり、約１モルである。 The amount of tertiary amine used is about 1 mole per mole of carbamoylaminomaleimide.
反応は、一般に、20〜150℃の範囲の温度で、
１〜50時間行なわれる。 The reaction is generally carried out at a temperature ranging from 20 to 150°C.
It lasts from 1 to 50 hours.
目的生成物である式〔〕で表わされるＮ−置
換アミノマレイミド類は結晶であるので、溶解度
の差を利用することによつて、反応生成混合物か
ら単離することができる。 Since the target product, the N-substituted aminomaleimide represented by the formula [], is a crystal, it can be isolated from the reaction product mixture by utilizing the difference in solubility.
この発明で得られるＮ−置換アミノマレイミド
類の具体例としては、１−クロロフエニル−３−
エトキシカルボニル−４−トルイジノマレイミ
ド、１−ブロモフエニル−３−エトキシカルボニ
ル−４−トリイジノアミノマレイミド、１−クロ
ロフエニル−３−エトキシカルボニル−４−メト
キシアニリノマレイミド、３−エトキシカルボニ
ル−４−メトキシアニリノ−１−トリルマレイミ
ド、３−エトキシカルボニル−１−トリル−４−
トルイジノマレイミド、１−クロロフエニル３−
メトキシカルボニル−４−トルイジノマレイミ
ド、３−メトキシカルボニル−４−メトキシアニ
リノ−１−トリルマレイミドなどが挙げられる。 Specific examples of N-substituted aminomaleimides obtained in this invention include 1-chlorophenyl-3-
Ethoxycarbonyl-4-toluidinomaleimide, 1-bromophenyl-3-ethoxycarbonyl-4-triidinoaminomaleimide, 1-chlorophenyl-3-ethoxycarbonyl-4-methoxyanilinomaleimide, 3-ethoxycarbonyl-4-methoxy Anilino-1-tolylmaleimide, 3-ethoxycarbonyl-1-tolyl-4-
Toluidinomaleimide, 1-chlorophenyl 3-
Examples include methoxycarbonyl-4-toluidinomaleimide and 3-methoxycarbonyl-4-methoxyanilino-1-tolylmaleimide.
つぎに実施例を示す。実施例において、Ｎ−置
換アミノマレイミド類の収率は、使用したカルバ
モイルアミノマレイミド類基準の値である。 Next, examples will be shown. In the Examples, the yield of N-substituted aminomaleimides is based on the carbamoylaminomaleimide used.
実施例 １
１−（ｐ−クロロフエニル）−３−エトキシカル
ボニル−４−（ｐ−トリルカルバモイル）アミノ
マレイミド0.93ｇとトリエテルアミン0.22ｇを含
むベンゼン10mlを加熱し、還流下に１時間反応さ
せた。Example 1 10 ml of benzene containing 0.93 g of 1-(p-chlorophenyl)-3-ethoxycarbonyl-4-(p-tolylcarbamoyl)aminomaleimide and 0.22 g of trietheramine was heated and reacted under reflux for 1 hour. .
反応後、得られた反応生成混合物を過し、
液を減圧下に濃縮した。残渣にベンゼンと酢酸エ
チルの容量比４：１の混合溶媒15mlを加えて過
し、液を、シリカゲル（ワコーゲルＣ−200、
100ｇ）を詰めたカラム（直径25mm）に通し、ベ
ンゼンと酢酸エチルの容量比４：１の混合溶媒で
溶離した。溶媒80mlで溶出したのち、溶媒200ml
で溶出して得た溶液を、減圧下に濃縮して、１−
（ｐ−クロロフエニル）−３−エトキシカルボニル
−４−（ｐ−トルイジノ）マレイミドの結晶0.31
ｇ（37％）を得た。これをエタノールで再結晶し
て、融点153〜154.5℃の微黄橙色結晶を得た。そ
の元素分析値をつぎに示す。 After the reaction, the resulting reaction product mixture is filtered,
The liquid was concentrated under reduced pressure. The residue was filtered by adding 15 ml of a mixed solvent of benzene and ethyl acetate in a volume ratio of 4:1, and the liquid was filtered using silica gel (Wako Gel C-200,
It was passed through a column (diameter 25 mm) packed with 100 g of ethyl acetate and eluted with a mixed solvent of benzene and ethyl acetate in a volume ratio of 4:1. After elution with 80 ml of solvent, 200 ml of solvent
The solution obtained by elution was concentrated under reduced pressure to obtain 1-
Crystals of (p-chlorophenyl)-3-ethoxycarbonyl-4-(p-toluidino)maleimide 0.31
g (37%). This was recrystallized from ethanol to obtain slightly yellowish orange crystals with a melting point of 153-154.5°C. The elemental analysis values are shown below.
Ｃ Ｈ Ｎ
分析値 62.87 4.53 7.60
計算値 62.42 4.45 7.28
（C20H17ClN2O4として）
実施例 ２
３−エトキシカルボニル−４−（ｐ−メトキシ
フエニルカルバモイル）アミノ−１−（ｐ−トリ
ル）マレイミド１ｇとトリエチルアミン0.24ｇを
含むベンゼン10mlを加熱し、還流下に１時間反応
させた。 C H N Analytical value 62.87 4.53 7.60 Calculated value 62.42 4.45 7.28 (as C 20 H 17 ClN 2 O 4 ) Example 2 3-Ethoxycarbonyl-4-(p-methoxyphenylcarbamoyl)amino-1-(p-tolyl) ) 10 ml of benzene containing 1 g of maleimide and 0.24 g of triethylamine was heated and reacted under reflux for 1 hour.
反応後、得られた反応生成混合物を過し、
液を減圧下に濃縮した。残渣にベンゼンと酢酸エ
チルの容量比５：１の混合溶媒15mlを加えて過
し、３−エトキシカルボニル−４−（ｐ−メトキ
シアニリノ）−１−（ｐ−トリル）マレイミドの結
晶0.15ｇ（17％）を得た。液を、シリカゲル
（ワコーゲルＣ−200、90ｇ）を詰めたカラム（直
径25mm）に通し、ベンゼンと酢酸エチルとの容量
比５：１の混合溶媒で溶離した。溶媒400mlで溶
出したのち、溶媒380mlで溶出して得た溶液を減
圧下に濃縮して、さらに３−エトキシカルボニル
−４−（ｐ−メトキシアニリノ）−１−（ｐ−トリ
ル）マレイミドの結晶0.4ｇ（45％）を得た。こ
れをエタノールで再結晶して、分解点148〜149℃
の黄色針状結晶を得た。その元素分析値をつぎに
示す。 After the reaction, the resulting reaction product mixture is filtered,
The liquid was concentrated under reduced pressure. The residue was filtered by adding 15 ml of a mixed solvent of benzene and ethyl acetate in a volume ratio of 5:1 to give 0.15 g of crystals of 3-ethoxycarbonyl-4-(p-methoxyanilino)-1-(p-tolyl)maleimide ( 17%). The liquid was passed through a column (diameter 25 mm) packed with silica gel (Wako Gel C-200, 90 g) and eluted with a mixed solvent of benzene and ethyl acetate in a volume ratio of 5:1. After elution with 400 ml of solvent, the solution obtained by elution with 380 ml of solvent was concentrated under reduced pressure to further obtain crystals of 3-ethoxycarbonyl-4-(p-methoxyanilino)-1-(p-tolyl)maleimide. 0.4g (45%) was obtained. This is recrystallized with ethanol, and the decomposition point is 148-149℃.
Yellow needle-like crystals were obtained. The elemental analysis values are shown below.
Ｃ Ｈ Ｎ 分析値 66.34 5.39 7.21 計算値 66.30 5.30 7.36 （C21H20N2O6として） C H N Analysis value 66.34 5.39 7.21 Calculated value 66.30 5.30 7.36 (as C 21 H 20 N 2 O 6 )
Claims (1)
ハロゲン原子を示し、R2は核の水素原子が炭素
数１〜４のアルキル基またはアルコキシ基で置換
されたフエニル基を示し、R3は炭素数２〜５の
アルコキシカルボニル基を示す。）で表わされる
カルバモイルアミノマレイミド類と第３アミンと
を反応させることを特徴とする 式 （式中、R1、R2およびR3は、それぞれ、前記と
同一の意味を有する。）で表わされるＮ−置換ア
ミノマレイミド類の製法。[Claims] 1 formula (In the formula, R 1 represents an alkyl group having 1 to 4 carbon atoms or a halogen atom, R 2 represents a phenyl group in which the hydrogen atom in the nucleus is substituted with an alkyl group or an alkoxy group having 1 to 4 carbon atoms, and R 3 represents an alkoxycarbonyl group having 2 to 5 carbon atoms.) A formula characterized by reacting a carbamoylaminomaleimide represented by the formula (3 represents an alkoxycarbonyl group having 2 to 5 carbon atoms) with a tertiary amine. A method for producing an N-substituted aminomaleimide represented by the formula (wherein R 1 , R 2 and R 3 each have the same meaning as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18689281A JPS5888360A (en) | 1981-11-24 | 1981-11-24 | Preparation of n-substituted aminomaleimide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18689281A JPS5888360A (en) | 1981-11-24 | 1981-11-24 | Preparation of n-substituted aminomaleimide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5888360A JPS5888360A (en) | 1983-05-26 |
| JPS645595B2 true JPS645595B2 (en) | 1989-01-31 |
Family
ID=16196507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18689281A Granted JPS5888360A (en) | 1981-11-24 | 1981-11-24 | Preparation of n-substituted aminomaleimide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5888360A (en) |
-
1981
- 1981-11-24 JP JP18689281A patent/JPS5888360A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5888360A (en) | 1983-05-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Synthesis and Biological Activity of N‐Aroyl (Aryloxyacetyl)‐N′‐ferrocenyl Thiourea Derivatives | |
| EP0052333B1 (en) | 4-fluoro-5-oxypyrazole derivate and preparation thereof | |
| JP4639382B2 (en) | Novel N-sulfenylbenzotriazole compound and method for producing the same | |
| JPS645595B2 (en) | ||
| JP4041881B2 (en) | Novel N-thio-substituted heterocyclic compound and method for producing the same | |
| JP4853911B2 (en) | Method for producing isothiazolopyridin-3-one compound | |
| JPS5888361A (en) | 3-amino-1,4-bis(alkoxycarbonyl)maleimide compound and its preparation | |
| US4587348A (en) | Process for preparing herbicidal 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide | |
| JPH06228149A (en) | Novel pentacyclic heterocyclic compound, production intermediate and their production | |
| JPH0216309B2 (en) | ||
| JP6868890B2 (en) | Method for producing nitrogen-containing cyclic compound having a substituent on the ring | |
| JP3038380B1 (en) | Method for producing ketene imine compound | |
| CA1164456A (en) | Process for the preparation of the 1-(4-chloro- benzoyl)-5-methoxy-2-methyl-3-indolyl- acetohydroxamic acid | |
| US5021587A (en) | Synthesis of N,3,4-trisubstituted-3-azoline-2-ones | |
| JP2671401B2 (en) | .ALPHA.-Aminothioacetamide derivative and its production method | |
| JPH0254357B2 (en) | ||
| JPH0376315B2 (en) | ||
| JP4982790B2 (en) | Method for producing isothiazolopyridin-3-one compound | |
| JPS645594B2 (en) | ||
| JPH0216314B2 (en) | ||
| JPH0216310B2 (en) | ||
| JPS6338992B2 (en) | ||
| JPH01168673A (en) | Production of 1,3-dialkylpyrazole-4-aldehydes | |
| EP0103840A2 (en) | Method for preparing 1,2,3-trihetero 5-membered heterocyclic compounds | |
| JPS5916879A (en) | Production of n-substituted imidazole |