GB920660A - New n-heterocyclic compounds and methods for their preparation - Google Patents
New n-heterocyclic compounds and methods for their preparationInfo
- Publication number
- GB920660A GB920660A GB2005260A GB2005260A GB920660A GB 920660 A GB920660 A GB 920660A GB 2005260 A GB2005260 A GB 2005260A GB 2005260 A GB2005260 A GB 2005260A GB 920660 A GB920660 A GB 920660A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- carbon atoms
- general formula
- heterocyclic compounds
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- -1 alkyl radical Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000002587 enol group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002691 malonic acids Chemical class 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises N-heterocyclic compounds of the general formula:- <FORM:0920660/IV(a)/1> wherein X represents the direct linkage or a divalent radical having 1-2 atoms in a direct chain between the two benzene nuclei, and Y and Z each represent hydrogen or halogen atoms or alkyl, alkoxy or alkylmercapto groups having at most 3 carbon atoms. The novel compounds may be made by condensing at a raised temperature a compound of the formula:- <FORM:0920660/IV(a)/2> with malonic acid by means of phosphorus oxychloride in the presence or absence of solvents or diluents. Suitable starting materials are specified. The new compounds are also made by heating compounds of the formula:- <FORM:0920660/IV(a)/3> wherein R represents a secondary alkyl radical or an arylmethyl radical and X, Y and Z are as above, with aluminium chloride or bromide, advantageously to temperatures of 200-260 DEG C., in which reaction diluents, e.g. phenol or sodium chloride, can be added. The starting materials of formula III are made by heating to 250-300 DEG C. N-heterocyclic compounds of formula II with esters of suitably substituted malonic acids and substituted phenols, in particular 2,4-dichlorophenol, or alkanols having at most 10 carbon atoms. Detailed examples describe the preparation of 8,9-malonyl carbazole, 9,10-malonylphenothiazine, 5,10-malonyl-9,10-dihydroacridine and 4,5-malonyliminodibenzyl. Compounds of the general formula <FORM:0920660/IV(a)/4> wherein Am represents a dialkylamino group containing a total of at most 10 carbon atoms, a polymethyleneimino or the morpholino group, and X, Y and Z have the meanings given above, are made by reacting alkali metal salts of the enol forms of compounds of general formula I with reactive esters of tertiary aminoalkylhalides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7417359 | 1959-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB920660A true GB920660A (en) | 1963-03-13 |
Family
ID=4533220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2005260A Expired GB920660A (en) | 1959-06-09 | 1960-06-08 | New n-heterocyclic compounds and methods for their preparation |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES258749A1 (en) |
| GB (1) | GB920660A (en) |
-
1960
- 1960-06-08 ES ES0258749A patent/ES258749A1/en not_active Expired
- 1960-06-08 GB GB2005260A patent/GB920660A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES258749A1 (en) | 1960-11-16 |
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