DE936748C - Process for the production of new Schiff bases - Google Patents
Process for the production of new Schiff basesInfo
- Publication number
- DE936748C DE936748C DEC9294A DEC0009294A DE936748C DE 936748 C DE936748 C DE 936748C DE C9294 A DEC9294 A DE C9294A DE C0009294 A DEC0009294 A DE C0009294A DE 936748 C DE936748 C DE 936748C
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- radical
- amino
- schiff bases
- oxy
- 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
- 239000002262 Schiff base Substances 0.000 title claims description 5
- 150000004753 Schiff bases Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- USRYWZFLGFQQEB-UHFFFAOYSA-N pyrimidin-5-ylmethanamine Chemical compound NCC1=CN=CN=C1 USRYWZFLGFQQEB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 nitro, amino Chemical group 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001549 tubercolostatic effect Effects 0.000 description 2
- 239000000814 tuberculostatic agent Substances 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- OZOHTVFCSKFMLL-UHFFFAOYSA-N 4-amino-5-aminomethyl-2-methylpyrimidine Chemical group CC1=NC=C(CN)C(N)=N1 OZOHTVFCSKFMLL-UHFFFAOYSA-N 0.000 description 1
- LHNLAKIPJRLKAZ-UHFFFAOYSA-N 5-(aminomethyl)-2,6-dimethylpyrimidin-4-amine dihydrochloride Chemical compound Cl.Cl.NC1=NC(=NC(=C1CN)C)C LHNLAKIPJRLKAZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ROSKZJGILXBSFM-UHFFFAOYSA-N pyrimidin-2-ylmethanamine Chemical compound NCC1=NC=CC=N1 ROSKZJGILXBSFM-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000766 tuberculocidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Description
Verfahren zur Herstellung neuer Schiffscher Basen Gegenstand der Erfindung bildet eine Reihe von neuen Schiffschen Basen von der allgemeinen Formel in welcher R1 ein Wasserstoffatom, einen Alkyl- oder Aralkylrest, eine Amino-, Alkylamino-, Alkoxy- oder Aralkoxy-, eine Thiol-, Alkyl-, Aralkylthiogruppe, eine Acyl- oder Aroylthiogruppe, R2 eine Oxy- oder Aminogruppe, R4 ein Wasserstoffatom oder einen Alkylrest, X einen geraden oder verzweigten Alkyl-oder Alkenylrest und R einen aromatischen oder isocychschen Rest, der durch Oxy-, Alkoxy-, Alkyl-, Nitro-, Amino-, Acylamino-, Alkyl- oder Dialkylamino-, Ureido-, N'-Alkylureidogruppen substituiert sein kann, bedeutet, sowie Salze solcher Verbindungen mit pharmakologisch verträglichen organischen oder anorganischen Säuren.Process for the preparation of new Schiff's bases The subject of the invention forms a series of new Schiff's bases of the general formula in which R1 is a hydrogen atom, an alkyl or aralkyl radical, an amino, alkylamino, alkoxy or aralkoxy, a thiol, alkyl, aralkylthio group, an acyl or aroylthio group, R2 is an oxy or amino group, R4 is a hydrogen atom or an alkyl radical, X a straight or branched alkyl or alkenyl radical and R an aromatic or isocyanic radical which is represented by oxy, alkoxy, alkyl, nitro, amino, acylamino, alkyl or dialkylamino, ureido, N'-alkylureido groups can be substituted, and also salts of such compounds with pharmacologically acceptable organic or inorganic acids.
Verbindungen, welche dieser vorerwähnten Formel entsprechen, besitzen wertvolle bakteriologische Eigenschaften. Sie sind beispielsweise befähigt, das Wachstum von Tbc-Keimen zu hemmen und sollen deshalb als Arzneimittel Verwendung finden.Compounds corresponding to the aforementioned formula have valuable bacteriological properties. You are for example capable of inhibiting the growth of Tbc germs and should therefore be used as a drug Find use.
Es ist bekannt, daß Benzaldehyd mit 2-Methyl-4-amino-5-aminomethylpyrimidin eine Schiffsche Base bildet (vgl. Berichte der deutschen chemischen Gesellschaft, Bd. 7o [r937], S. 2046/2047). Diese zeigt keine praktisch verwertbare tuberkulostatische und keine tuberkulocide Wirkung, während die aus araliphatischen Aldehyden und entsprechenden 5-Aminomethylpyrimidinen gebildeten Schiffschen Basen tuberkulostatisch und tuberkulocid gut bis sehr gut wirksam sind.It is known that benzaldehyde with 2-methyl-4-amino-5-aminomethylpyrimidine forms a Schiff base (see reports of the German chemical society, Vol. 7o [r937], pp. 2046/2047). This shows no practically usable tuberculostatic and no tuberculocidal effect, while those from araliphatic aldehydes and corresponding 5-aminomethylpyrimidines formed Schiff bases tuberculostatic and tuberculocid are good to very effective.
Die Herstellung der Verbindungen erfolgt nach an sich -bekannten Verfahren durch Umsetzung eines Aminomethylpyrimidins der Formel in welcher R1, R2 und R4 die bereits erwähnte Bedeutung zukommt, mit einer Verbindung, welche zur Einführung des Restes in die Aminomethylgruppe geeignet ist, worin R und X die bereits erwähnte Bedeutung zukommt.The compounds are prepared by processes known per se by reacting an aminomethylpyrimidine of the formula in which R1, R2 and R4 have the meaning already mentioned, with a compound which leads to the introduction of the remainder is suitable in the aminomethyl group, in which R and X have the meaning already mentioned.
Als Verbindungen, welche diesen Rest (III) in die Aminomethylgruppe einführen können, seien genannt die entsprechenden Aldehyde, ihre Acetale und Acylderivate und die entsprechenden Dihalogenide. Die 5-Aminomethylpyrimidine der Formel (II) können in Form der freien Base oder auch als Säuresalze zur Reaktion gebracht werden, wobei man dann vor, während oder nach Zusatz der zweiten. Reaktionskomponente die der Säure entsprechende Menge Alkali zufügt.As compounds which convert this radical (III) into the aminomethyl group can introduce the corresponding aldehydes, their acetals and acyl derivatives and the corresponding dihalides. The 5-aminomethylpyrimidines of the formula (II) can be reacted in the form of the free base or as acid salts, then before, during or after the addition of the second. Reaction component the add the appropriate amount of alkali to the acid.
Verwendet man z. B. ein Dihalogenid, so arbeitet man vorteilhaft in Gegenwart eines basischen Kondensationsmittels, wie Alkalihydroxyden, Oxyden, Karbonaten, Alkoholaten. Im allgemeinen ist das Arbeiten in einem Lösungsmittel angezeigt, jedoch nicht unbedingt erforderlich. Als Lösungsmittel eignen sich z. B. Alkohole vorzüglich.If you use z. B. a dihalide, it is advantageous to work in Presence of a basic condensing agent, such as alkali hydroxides, oxides, carbonates, Alcoholates. In general, however, working in a solvent is indicated not necessarily required. Suitable solvents are, for. B. Alcohols excellent.
Verbindungen, in denen R2 eine Aminogruppe bedeutet, besitzen wahrscheinlich die folgende Konfiguration Auf diese Struktur konnte auf Grund der für solche Verbindungen erhaltenen Absorptionsspektren mit großer Wahrscheinlichkeit geschlossen werden.Compounds in which R2 represents an amino group are likely to have the following configuration This structure could be inferred with great probability on the basis of the absorption spectra obtained for such compounds.
Beispiel 5 g 2, 6-Dimethyl-4-amino-5-aminomethylpyrimidindihydrochlorid werden in einer Lösung von 1,03 g Natrium in 50 ccm Methanol aufgeschlämmt, und die Suspension wird mit 3 g Zimtaldehyd in 15 ccm Methanol versetzt. Man erhitzt 2o Minuten zum Sieden,- verdampft das Ganze im Vakuum und verreibt den Rückstand in Wasser. Anschließend wird aus Benzol tonkristallisiert. Man erhält 3 g 5-Cinnamalaminomethyl-2, 6-dimethyl-4-aminopyrimidin [2, 6-Dimethyl-2-styryl-i', 2', 3', 4'-tetrahydropyrimido-(5', 6': 5, 4)-pyrimidin], das bei 12o bis 122° schmilzt.Example 5 g of 2,6-dimethyl-4-amino-5-aminomethylpyrimidine dihydrochloride are slurried in a solution of 1.03 g of sodium in 50 ccm of methanol, and 3 g of cinnamaldehyde in 15 cc of methanol are added to the suspension. One heats up 20 minutes to the boil - the whole thing evaporates in vacuo and rubs off the residue in water. Then it is clay crystallized from benzene. 3 g of 5-cinnamalaminomethyl-2 are obtained, 6-dimethyl-4-aminopyrimidine [2,6-dimethyl-2-styryl-i ', 2', 3 ', 4'-tetrahydropyrimido- (5', 6 ': 5, 4) -pyrimidine], which melts at 12o to 122 °.
In der gleichen Weise erhält man folgende in 2'-Stellung substituierte
2, 6-Dimethyl-1', 2', 3', 4'-tetrahydropyrimido-(5', 6': 5, 4)-pyrimidine:
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH936748X | 1953-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE936748C true DE936748C (en) | 1955-12-22 |
Family
ID=4549170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC9294A Expired DE936748C (en) | 1953-03-31 | 1953-06-26 | Process for the production of new Schiff bases |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE936748C (en) |
-
1953
- 1953-06-26 DE DEC9294A patent/DE936748C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
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