DE1149007B - Process for the preparation of acyl hydrazide hydrazones - Google Patents
Process for the preparation of acyl hydrazide hydrazonesInfo
- Publication number
- DE1149007B DE1149007B DEB48813A DEB0048813A DE1149007B DE 1149007 B DE1149007 B DE 1149007B DE B48813 A DEB48813 A DE B48813A DE B0048813 A DEB0048813 A DE B0048813A DE 1149007 B DE1149007 B DE 1149007B
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- parts
- hydrazones
- acyl hydrazide
- hydrazide
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Description
Verfahren zur Herstellung von Acyl-hydrazid-hydrazonen Es wurde gefunden, daß man Acyl-hydrazidhydrazone erhält, wenn man Protoanemonin bzw. dessen Homologe mit Isonicotinsäurehydrazid bei erhöhter Temperatur umsetzt.Process for the preparation of acyl hydrazide hydrazones It has been found that acyl hydrazide hydrazones are obtained if protoanemonin or its homologues are used with isonicotinic acid hydrazide at elevated temperature.
Es ist bereits bekannt, ungesättigte y-Lactone, z. B. Penten-(3)-olid-(4,1) oder Hexen-(3)-olid-(4, 1), mit etwa doppelt molaren Mengen Isonicotinsäurehydrazid unter Erhitzung zu den Isonicotinoylhydrazonen der y-Ketosäureisonicotinoylhydrazide umzusetzen. Demgegenüber erhält man bei dem erfindungsgemäßen Verfahren neue Verbindungen, bei denen das konjugierte System der beiden Kohlenstoff-Kohlenstoff-Doppelbindungen des Protoanemonins bzw. Methylprotoanemonins durch ein konjugiertes System einer Kohlenstoff-Kohlenstoff-Doppelbindung mit einer Kohlenstoff-Stickstoff-Doppelbindung ersetzt. ist. Die nach dem Verfahren hergestellten Hydrazid-hydrazone der ß-Acylacrylsäuren sind antibakterielle Mittel, insbesondere gegen Mykobakterien. It is already known to use unsaturated γ-lactones, e.g. B. pentene- (3) -olide- (4.1) or hexen- (3) -olide- (4, 1), with about twice the molar amounts of isonicotinic acid hydrazide on heating to the isonicotinoylhydrazones of the γ-keto acid isonicotinoylhydrazides to implement. In contrast, the process according to the invention gives new compounds, in which the conjugated system of the two carbon-carbon double bonds des Protoanemonins or Methylprotoanemonins by a conjugated system of a Carbon-carbon double bond with a carbon-nitrogen double bond replaced. is. The hydrazide hydrazones of β-acylacrylic acids produced by the process are antibacterial agents, especially against mycobacteria.
Als Ausgangsstoffe verwendet man Protoanemonin bzw. dessen Homologe, z. B. das Methylprotoanemonin, und Isonicotinsäurehydrazid. Protoanemonin or its homologues are used as starting materials, z. B. methyl protoanemonine, and isonicotinic acid hydrazide.
Die Umsetzung kann am Beispiel des Methylprotoanemonins, auch Homoprotoanemonin genannt, und des Isonicotinsäurehydrazids wie folgt formelmäßig dargestellt werden: Es bildet sich das Isonicotinoylhydrazon des ß-Propionyl-acrylsäure-isonicotinoyl-hydrazids.The reaction can be represented by the example of methyl protoanemonine, also called homoprotoanemonine, and isonicotinic acid hydrazide as follows: The isonicotinoyl hydrazone of the ß-propionyl-acrylic acid-isonicotinoyl-hydrazide is formed.
Die Umsetzung kann z. B. durch einfaches Zusammenschmelzen der beiden Ausgangsstoffe durchgeführt werden. Man kann aber auch die beiden Ausgangsstoffe in einem inerten Lösungsmittel oder Verdünnungsmittel durch Erhitzen umsetzen. Als inertes Lösungs- oder Verdünnungsmittel eignen sich z. B. Alkohole, wie Butanol, Äther, wie Dioxan oder Glykoläther, oder Säureamide, wie Dimethylformamid. The implementation can e.g. B. by simply fusing the two together Starting materials are carried out. But you can also use the two starting materials React in an inert solvent or diluent by heating. as Inert solvents or diluents are suitable, for. B. alcohols such as butanol, Ethers, such as dioxane or glycol ethers, or acid amides, such as dimethylformamide.
Die Umsetzung wird bei erhöhter Temperatur, z. B. bei 100 bis 200°C, vorteilhaft bei 150 bis 1800C, vorgenommen. Das bei der Umsetzung entstehende Reaktionswasser kann z. B. aus der Schmelze unter vermindertem Druck abgezogen oder bei Verwendung von Lösungs- oder Verdünnungsmitteln durch Auskreisen aus dem Umsetzungsgemlsch entfernt werden. The reaction is carried out at an elevated temperature, e.g. B. at 100 to 200 ° C, advantageously at 150 to 1800C. The water of reaction formed during the reaction can e.g. B. withdrawn from the melt under reduced pressure or when used of solvents or diluents by removing them from the reaction mixture removed.
Man kann bei Normaldruck, aber auch unter vermindertem Druck arbeiten. Vorteilhaft wird die Reaktion in einer inerten Atmosphäre ausgeführt, d. h. unter Ausschluß von Sauerstoff und in Gegenwart von inerten Gasen, wie Stickstoff oder Kohlendioxyd.You can work under normal pressure, but also under reduced pressure. The reaction is advantageously carried out in an inert atmosphere; H. under Exclusion of oxygen and in the presence of inert gases such as nitrogen or Carbon dioxide.
Die in den Beispielen genannten Teile sind Gewichtsteile. The parts mentioned in the examples are parts by weight.
Beispiel 1 In einem Rundkolben werden 24 Teile Isonicotinsäurehydrazid unter Stickstoff geschmolzen. Bei einer Badtemperatur von etwa 190"C läßt man langsam 22 Teile Methylprotoanemonin zutropfen. Die Schmelze wird nach etwa 15 Minuten homogen und wird weitere 15 Minuten bei 190 bis 200"C Badtemperatur gehalten. Nach dem Erkalten nimmt man die Schmelze in Methanol auf, es scheiden sich 10 Teile eines festen Stoffes durch Kristallisation aus, der aus Alkohol umkristallisiert einen Schmelzpunkt von 251 bis 253"C aufweist. Example 1 In a round bottom flask, 24 parts of isonicotinic acid hydrazide are added melted under nitrogen. At a bath temperature of about 190 ° C., the mixture is left slowly 22 parts of methylprotoanemonine are added dropwise. The melt becomes homogeneous after about 15 minutes and is kept at a bath temperature of 190 to 200 "C. for a further 15 minutes. After cooling if the melt is taken up in methanol, it separates 10 parts of a solid substance through crystallization, which recrystallizes from alcohol has a melting point of 251 to 253 "C.
ClsH1sN603.ClsH1sN603.
Berechnet .... C 59,01, H 4,82, N 22,85%; gefunden . .. C58,43, H 4,67, N22,43%. Calculated .... C 59.01, H 4.82, N 22.85%; found . .. C58.43, H. 4.67, N22.43%.
Beispiel 2 12 Teile Isonicotinsäurehydrazid werden in 200 Teilen n-Butanol bei etwa 110°C unter Rühren mit 11 Teilen Methylprotoanemonin in 50 Teilen ButanoI versetzt. Man läßt anschließend noch etwa 15 Minuten unter Rückfluß kochen. Nach dem Ein- engen unter vermindertem Druck nimmt man in Methanol auf und erhält 5 Teile des im Beispiel 1 beschriebenen Produktes. Example 2 12 parts of isonicotinic acid hydrazide are used in 200 parts n-butanol at about 110 ° C. with stirring with 11 parts of methyl protoanemonine in 50 parts ButanoI added. The mixture is then refluxed for about 15 minutes. After entering narrow under reduced pressure is taken up in methanol and obtained 5 parts of the product described in Example 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB48813A DE1149007B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of acyl hydrazide hydrazones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB48813A DE1149007B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of acyl hydrazide hydrazones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1149007B true DE1149007B (en) | 1963-05-22 |
Family
ID=6968695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB48813A Pending DE1149007B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of acyl hydrazide hydrazones |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1149007B (en) |
-
1958
- 1958-05-06 DE DEB48813A patent/DE1149007B/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1445024A1 (en) | Process for the preparation of monomeric N-heterocyclic compounds | |
| DE705530C (en) | Process for the preparation of polychloride substitution products of diphenyl ether | |
| DE1149007B (en) | Process for the preparation of acyl hydrazide hydrazones | |
| DE1470350B1 (en) | 5,6-dihydro-morphanthridines and process for their preparation | |
| DE602218C (en) | Process for the preparation of pyridylhydantoins | |
| DE947553C (en) | Process for the preparation of imino-amino-methanesulfinic acid | |
| DE890645C (en) | Process for the preparation of cyanuric halides ^ | |
| DE937058C (en) | Process for the preparation of low molecular weight trialkylamine oxides and their hydrates | |
| DE845520C (en) | Process for the preparation of quaternary ammonium compounds | |
| DE838140C (en) | Process for the preparation of amino-aryl-pyridlyl-alkanols and their esters | |
| DE1128424B (en) | Process for the preparation of 7-alkylthio- and 7-alkenylthio-4-androsten-3-ones | |
| DE964496C (en) | Process for the recovery of the excess formaldehyde and nitric acid obtained in the manufacture of cyclotrimethylene trinitramine | |
| DE952814C (en) | Process for the preparation of 3, 4, 5-trioxyotetrahydropyran | |
| DE767834C (en) | Process for the preparation of o-dicarboximides | |
| DE953013C (en) | Process for the production of polycondensation products | |
| DE896350C (en) | Process for the preparation of 4-monoalkylaminosalicylic acids and 4-monoalkyloxyalkylaminosalicylic acids | |
| DE1118215B (en) | Process for the preparation of 2, 5-dianilino-terephthalic acid esters | |
| AT249048B (en) | Process for the preparation of new benzimidazolone derivatives | |
| DE736024C (en) | Process for the production of oxygen-containing anthracene fragments | |
| DE871755C (en) | Process for the production of carboxylic acid amides and carboxylic acids | |
| AT221503B (en) | Process for the production of new basic phenol ethers and their salts | |
| DE1445918C (en) | Process for the preparation of bipyridyls optionally substituted by one or more low molecular weight alkyl groups | |
| DE1159465B (en) | Process for the preparation of 2-chloro-4-azaphenthiazine | |
| DE1224726B (en) | Process for the preparation of 2, 5-dialkoxybenzaldehydes | |
| DE1123330B (en) | Process for the preparation of 3,3-dialkyl-diazacyclopropanes |