JPS6154791B2 - - Google Patents
Info
- Publication number
- JPS6154791B2 JPS6154791B2 JP13631481A JP13631481A JPS6154791B2 JP S6154791 B2 JPS6154791 B2 JP S6154791B2 JP 13631481 A JP13631481 A JP 13631481A JP 13631481 A JP13631481 A JP 13631481A JP S6154791 B2 JPS6154791 B2 JP S6154791B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- substituted
- acrolein
- dialkylamino
- 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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- -1 aryl 1,2-dithiolium salt Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- FGGPJHXGBZNABQ-UHFFFAOYSA-N (2-aminophenyl)cyanamide Chemical compound NC1=CC=CC=C1NC#N FGGPJHXGBZNABQ-UHFFFAOYSA-N 0.000 description 1
- HJUREEORHHYGAX-UHFFFAOYSA-N 1-(2-nitrophenyl)prop-2-en-1-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C=C HJUREEORHHYGAX-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RGJXMMUQTCONEI-UHFFFAOYSA-N 3,4-diaminobenzamide Chemical compound NC(=O)C1=CC=C(N)C(N)=C1 RGJXMMUQTCONEI-UHFFFAOYSA-N 0.000 description 1
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 1
- IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- GHZJXHZYWCNUKC-UHFFFAOYSA-N 4-(methoxymethyl)benzene-1,2-diamine Chemical compound COCC1=CC=C(N)C(N)=C1 GHZJXHZYWCNUKC-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- AEPYIICGYIUTCV-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,2,4-triamine Chemical compound CN(C)C1=CC=C(N)C(N)=C1 AEPYIICGYIUTCV-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- KYEFUIBOKLKQPD-UHFFFAOYSA-N 4-phenylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=CC=C1 KYEFUIBOKLKQPD-UHFFFAOYSA-N 0.000 description 1
- PENDLXYAEYGSTB-UHFFFAOYSA-N 5-(dimethylamino)pent-1-en-3-one Chemical compound CN(C)CCC(=O)C=C PENDLXYAEYGSTB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- GQHXIJFHBJFZQZ-UHFFFAOYSA-N ethyl 2-(3,4-diaminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C(N)=C1 GQHXIJFHBJFZQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13631481A JPS5838272A (ja) | 1981-08-31 | 1981-08-31 | テトラアザアヌレン誘導体の製造方法 |
| US06/409,919 US4465630A (en) | 1981-08-24 | 1982-08-20 | Tetraazaannulene cobalt complex compounds and method for preparation therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13631481A JPS5838272A (ja) | 1981-08-31 | 1981-08-31 | テトラアザアヌレン誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5838272A JPS5838272A (ja) | 1983-03-05 |
| JPS6154791B2 true JPS6154791B2 (en]) | 1986-11-25 |
Family
ID=15172302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13631481A Granted JPS5838272A (ja) | 1981-08-24 | 1981-08-31 | テトラアザアヌレン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5838272A (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0425689U (en]) * | 1990-06-20 | 1992-02-28 |
-
1981
- 1981-08-31 JP JP13631481A patent/JPS5838272A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0425689U (en]) * | 1990-06-20 | 1992-02-28 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5838272A (ja) | 1983-03-05 |
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