GB914717A - New n-heterocyclic compounds - Google Patents
New n-heterocyclic compoundsInfo
- Publication number
- GB914717A GB914717A GB4119159A GB4119159A GB914717A GB 914717 A GB914717 A GB 914717A GB 4119159 A GB4119159 A GB 4119159A GB 4119159 A GB4119159 A GB 4119159A GB 914717 A GB914717 A GB 914717A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- acyl
- iminodibenzyl
- dibenzo
- reacting
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 2
- -1 acetyl halide Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000012954 diazonium Substances 0.000 abstract 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 239000012433 hydrogen halide Substances 0.000 abstract 2
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- BEWVAZNECYSPMT-UHFFFAOYSA-N 2,3-dihydro-1h-azepine Chemical compound C1CC=CC=CN1 BEWVAZNECYSPMT-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001538 azepines Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 3-substituted 10.11dihydro-5H-dibenzo[b.f]azepine, and 3-substituted 5H-dibenzo[b.f]azepines of general formula <PICT:0914717/IV (b)/1> where X represents the ethylene or vinylene group and Y, chlorine or bromine which are prepared by reacting a 5-acyl iminodibenzyl in the presence of a Friedel Crafts condensing agent, with an acetyl halide or acetanhydride, converting the resulting 3-acetyl-5-acyl by hydrazoic acid into a 3-acetamido-5-acyl imino-dibenzyl, partially hydrolysing to 3-amino-5-acyl imino-dibenzyl converting into a diazonium salt, reacting with cuprous halide and hydrolysing the product to the dihydro azepine, and halogenating, reacting the 3-substituted 5-acyl-10-halogen iminodibenzyl to split off hydrogen halide and hydrolysing the 3-substituted 5-acyl iminostilbene to the 3-substituted-5H-dibenzo azepine where X is the vinylene group. The reaction product of the 3-amino-5-iminodibenzyl diazonium salt with cuprous halide according to Sandmeyer, may be treated with N-bromosuccinimide or with 1.3-dibromo-5.5-dimethyl hydantion, N-chlorosuccinimide, N-bromophthalimide, or Nbromoacetamide to form a 3-substituted 5-acyl-10-halogen iminodibenzyl. The splitting of the hydrogen halide and the hydrolysis stages may be performed concurrently. An alternative process for the preparation is by the hydrogenation of 3.7-dihaloiminodibenzyl in the presence of a catalyst such as Raney nickel, or noble metals, and an inorganic or organic base in solvents such as methanol, ethanol, methoxyethanol and dioxane. The compounds may be used as intermediates in the production of compounds substituted in the imino group having therapeutic properties. Specification 777,546 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6704858 | 1958-12-06 | ||
| CH6820059A CH375360A (en) | 1959-01-12 | 1959-01-12 | Process for the preparation of new N-heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB914717A true GB914717A (en) | 1963-01-02 |
Family
ID=25737905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4119159A Expired GB914717A (en) | 1958-12-06 | 1959-12-04 | New n-heterocyclic compounds |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE585357A (en) |
| ES (1) | ES253959A1 (en) |
| GB (1) | GB914717A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076812A (en) * | 1974-09-27 | 1978-02-28 | Ciba-Geigy Corporation | 10-Halogeno- or 10,11-dihalogeno derivatives of 5H-dibenz[b,f]azepine |
-
1959
- 1959-12-04 BE BE585357A patent/BE585357A/en unknown
- 1959-12-04 GB GB4119159A patent/GB914717A/en not_active Expired
- 1959-12-05 ES ES0253959A patent/ES253959A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076812A (en) * | 1974-09-27 | 1978-02-28 | Ciba-Geigy Corporation | 10-Halogeno- or 10,11-dihalogeno derivatives of 5H-dibenz[b,f]azepine |
Also Published As
| Publication number | Publication date |
|---|---|
| BE585357A (en) | 1960-06-07 |
| ES253959A1 (en) | 1960-05-16 |
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