GB1335306A - Process for the oxidative dehydrocyclization of imines - Google Patents
Process for the oxidative dehydrocyclization of iminesInfo
- Publication number
- GB1335306A GB1335306A GB5073471A GB5073471A GB1335306A GB 1335306 A GB1335306 A GB 1335306A GB 5073471 A GB5073471 A GB 5073471A GB 5073471 A GB5073471 A GB 5073471A GB 1335306 A GB1335306 A GB 1335306A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- toluidine
- aniline
- carried out
- oxygen
- 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
- 150000002466 imines Chemical class 0.000 title abstract 4
- 230000001590 oxidative effect Effects 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 abstract 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- -1 alkaryl radical Chemical class 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 239000008246 gaseous mixture Substances 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 abstract 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- PYFVEIDRTLBMHG-UHFFFAOYSA-N 2,3-dimethyl-1h-indole Chemical compound C1=CC=C2C(C)=C(C)NC2=C1 PYFVEIDRTLBMHG-UHFFFAOYSA-N 0.000 abstract 1
- PDSPNGGVEIUMHV-UHFFFAOYSA-N 2-methylindole Chemical compound C1=C[CH]C2=NC(C)=CC2=C1 PDSPNGGVEIUMHV-UHFFFAOYSA-N 0.000 abstract 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-metylindole Natural products C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 abstract 1
- 101100533558 Mus musculus Sipa1 gene Proteins 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000004645 aluminates Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- CBXWICRJSHEQJT-UHFFFAOYSA-N n,1-diphenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=CC=C1 CBXWICRJSHEQJT-UHFFFAOYSA-N 0.000 abstract 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 abstract 1
- XCYDGNRLVROJKQ-UHFFFAOYSA-N n-(2-methylphenyl)-1-phenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=CC=C1C XCYDGNRLVROJKQ-UHFFFAOYSA-N 0.000 abstract 1
- PUUAIRXOPHLROM-UHFFFAOYSA-N n-(2-methylphenyl)-1-phenylmethanimine Chemical compound CC1=CC=CC=C1N=CC1=CC=CC=C1 PUUAIRXOPHLROM-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTHLLNWIVET-UHFFFAOYSA-N n-(2-methylphenyl)propan-2-imine Chemical compound CC(C)=NC1=CC=CC=C1C RJWBTHLLNWIVET-UHFFFAOYSA-N 0.000 abstract 1
- ZVYCPFCNAXPUFP-UHFFFAOYSA-N n-ethylpropan-1-imine Chemical compound CCC=NCC ZVYCPFCNAXPUFP-UHFFFAOYSA-N 0.000 abstract 1
- FZVGLJHAOUNCRS-UHFFFAOYSA-N n-phenylbutan-2-imine Chemical compound CCC(C)=NC1=CC=CC=C1 FZVGLJHAOUNCRS-UHFFFAOYSA-N 0.000 abstract 1
- YEYCASGOSICVMZ-UHFFFAOYSA-N n-phenylpropan-2-imine Chemical compound CC(C)=NC1=CC=CC=C1 YEYCASGOSICVMZ-UHFFFAOYSA-N 0.000 abstract 1
- FBXWQCRRTFRZDA-UHFFFAOYSA-N n-propylethanimine Chemical compound CCCN=CC FBXWQCRRTFRZDA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3126070 | 1970-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1335306A true GB1335306A (en) | 1973-10-24 |
Family
ID=11233351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5073471A Expired GB1335306A (en) | 1970-11-02 | 1971-11-01 | Process for the oxidative dehydrocyclization of imines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3845072A (enExample) |
| AT (1) | AT309411B (enExample) |
| BE (1) | BE774379A (enExample) |
| CA (1) | CA958017A (enExample) |
| CH (1) | CH553779A (enExample) |
| ES (1) | ES396679A1 (enExample) |
| FR (1) | FR2113386A5 (enExample) |
| GB (1) | GB1335306A (enExample) |
| HU (1) | HU166623B (enExample) |
| LU (1) | LU64184A1 (enExample) |
| NL (1) | NL153532B (enExample) |
| SE (1) | SE390966B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1253508A (en) * | 1984-11-19 | 1989-05-02 | Mitsui Chemicals, Incorporated | Preparation process of indoles |
-
1971
- 1971-10-22 ES ES396679A patent/ES396679A1/es not_active Expired
- 1971-10-22 CA CA125,902A patent/CA958017A/en not_active Expired
- 1971-10-22 BE BE774379A patent/BE774379A/xx unknown
- 1971-10-29 FR FR7138933A patent/FR2113386A5/fr not_active Expired
- 1971-10-29 LU LU64184D patent/LU64184A1/xx unknown
- 1971-10-29 CH CH1577471A patent/CH553779A/fr not_active IP Right Cessation
- 1971-11-01 SE SE7113898A patent/SE390966B/xx unknown
- 1971-11-01 GB GB5073471A patent/GB1335306A/en not_active Expired
- 1971-11-02 NL NL717115095A patent/NL153532B/xx unknown
- 1971-11-02 AT AT942671A patent/AT309411B/de not_active IP Right Cessation
- 1971-11-02 HU HUSA2270A patent/HU166623B/hu unknown
- 1971-11-02 US US00194926A patent/US3845072A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3845072A (en) | 1974-10-29 |
| HU166623B (enExample) | 1975-04-28 |
| DE2154482A1 (de) | 1972-12-14 |
| BE774379A (fr) | 1972-02-14 |
| LU64184A1 (enExample) | 1972-05-15 |
| NL153532B (nl) | 1977-06-15 |
| DE2154482B2 (de) | 1976-03-04 |
| ES396679A1 (es) | 1974-05-16 |
| CA958017A (en) | 1974-11-19 |
| SE390966B (sv) | 1977-01-31 |
| FR2113386A5 (enExample) | 1972-06-23 |
| AT309411B (de) | 1973-08-27 |
| NL7115095A (enExample) | 1972-05-04 |
| CH553779A (fr) | 1974-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |