DE102021006309A1 - Composition with dithiol and diamino functionality - Google Patents
Composition with dithiol and diamino functionality Download PDFInfo
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- DE102021006309A1 DE102021006309A1 DE102021006309.0A DE102021006309A DE102021006309A1 DE 102021006309 A1 DE102021006309 A1 DE 102021006309A1 DE 102021006309 A DE102021006309 A DE 102021006309A DE 102021006309 A1 DE102021006309 A1 DE 102021006309A1
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- Germany
- Prior art keywords
- acids
- diamino
- compounds
- dithiol
- azides
- 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
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- 150000004662 dithiols Chemical class 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title claims description 7
- -1 imidines Chemical class 0.000 claims abstract description 15
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000001408 amides Chemical class 0.000 claims abstract description 4
- 150000001409 amidines Chemical class 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 150000001540 azides Chemical class 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 150000003949 imides Chemical class 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- 150000002596 lactones Chemical class 0.000 claims abstract description 4
- 150000002825 nitriles Chemical class 0.000 claims abstract description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
- 150000003457 sulfones Chemical class 0.000 claims abstract description 4
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 4
- 150000003568 thioethers Chemical class 0.000 claims abstract description 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims abstract description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001298 alcohols Chemical class 0.000 claims abstract description 3
- 150000001413 amino acids Chemical class 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000001731 carboxylic acid azides Chemical class 0.000 claims abstract description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
- 150000002170 ethers Chemical class 0.000 claims abstract description 3
- 150000004820 halides Chemical class 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 235000000346 sugar Nutrition 0.000 claims abstract description 3
- 150000008163 sugars Chemical class 0.000 claims abstract description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims abstract description 3
- 125000005323 thioketone group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003573 thiols Chemical group 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- QESFEZQJGHQGJO-UHFFFAOYSA-N 2h-thieno[3,2-b]thiopyran-2,5-diamine Chemical compound C1=C(N)SC2=CC(N)SC2=C1 QESFEZQJGHQGJO-UHFFFAOYSA-N 0.000 description 1
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/34—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a mercapto group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Die Erfindung betrifft ein neues Molekül mit Dithiol- und Diamino-Funktionalität, als Grundbaustein zur Herstellung verschiedener Komplexe und Verbindungen.Der Erfindung liegt die Aufgabe zugrunde, ein gut zugängliches und einfaches Molekül mit Dithiol- und Diamino-Funktionalität herzustellen, welches unter Luft und Zimmertemperatur stabil ist, als auch einfach modifiziert werden kann.Als besagte Bausteine können Verbindungen mit der allgemeinen Formel (VII) eingesetzt werden.Wobei R und R' gleich oder unterschiedliche Substituenten der Klassifizierung: H-, Alkyl-, Cycloalkyl-, Aryl- oder Heteroarylverbindungen, Heterozyklen, Alkohole, Mercaptane, Amine, Nitrile, Carbonsäuren, Amide, Imide, Hydroxamsäuren, Aminosäuren, Zucker, Ether, Thioether, Ketone, Thioketone, Aldehyde, Thioaldehyde, Ester, Imidine, Amidine, Sulfonsäuren, Sulfoxide, Sulfonamide, Sulfone, Azide, Carbonsäureazide, Peptide, Lactone, Thiolactone oder Halogenide sein können.The invention relates to a new molecule with dithiol and diamino functionality as a basic building block for the production of various complexes and compounds is stable and can also be easily modified.Compounds with the general formula (VII) can be used as said building blocks.R and R' being the same or different substituents of the classification: H, alkyl, cycloalkyl, aryl or heteroaryl compounds , Heterocycles, alcohols, mercaptans, amines, nitriles, carboxylic acids, amides, imides, hydroxamic acids, amino acids, sugars, ethers, thioethers, ketones, thioketones, aldehydes, thioaldehydes, esters, imidines, amidines, sulfonic acids, sulfoxides, sulfonamides, sulfones, azides , carboxylic acid azides, peptides, lactones, thiolactones or halides can be.
Description
Die Erfindung betrifft ein neues Molekül mit Dithiol- und Diamino-Funktionalität, als Grundbaustein zur Herstellung verschiedener Komplexe und Verbindungen.The invention relates to a new molecule with dithiol and diamino functionality as a basic building block for the production of various complexes and compounds.
Zurzeit sind diverse Benzolderivate bekannt, die verschiedenste Substitutionsmuster mit jeweils zwei Amino- und Thiol-Funktionalitäten aufweisen.
Bekannte Verbindungen mit mindestens zwei Thiol- und zwei Amino-Gruppen sind 4,6-Diamino-1,3-benzodithiol bekannt aus
Known compounds with at least two thiol and two amino groups are known from 4,6-diamino-1,3-benzodithiol
Aus G. Grandolini, A. Martani, Gazzetta Chimica Italiana 1962, 1150 sind 2,4,6-Triamino-1,3,5-benzotrithiol (III)
Darüber hinaus bekannt ist 2,6-Diamino-3,5-anisoldithiol aus J. W. L. Wong, A. Mailman, S. M. Winter, C. M. Robertson, R. J. Holmberg, M. Murugesu, P. A. Dube, R. T. Oakley, Chemical communications (Cambridge, England) 2014, 50, 785. (V)
Von den aufgeführten Molekülen besitzt jedoch keines ein Substitutionsmuster mit zueinander benachbarten Diamino- bzw. Dithiol-Gruppen. Der Nachteil hierbei ist, dass es nicht möglich ist Komplexe mit gleichen Donoratomen herzustellen. Daraus ergeben sich für die bekannten Verbindungen Einschränkungen bei der weiteren Verwendung.
Nach dem heutigen Stand der Technik ist keine Beschreibung oder direkte Synthese eines solchen Moleküls bekannt.However, none of the molecules listed has a substitution pattern with mutually adjacent diamino or dithiol groups. The disadvantage here is that it is not possible to produce complexes with the same donor atoms. This results in restrictions for the further use of the known compounds.
According to the present state of the art, no description or direct synthesis of such a molecule is known.
Der Erfindung liegt die Aufgabe zugrunde, ein gut zugängliches und einfaches Molekül mit Dithiol- und Diamino-Funktionalität herzustellen, welches unter Luft und Zimmertemperatur stabil ist, als auch einfach modifiziert werden kann.
Unerwarteter Weise wurde entdeckt, dass es möglich war, ein Molekül herzustellen, welches diese Ansprüche erfüllt und an Luft und bei Zimmertemperatur als Feststoff stabil ist. Die Herstellung des Moleküls erfordert keinen großen synthetischen Aufwand, um gute Ausbeuten zu erreichen. Es zeichnet sich dadurch aus, dass es in 1,2-Position Thiol-Gruppen und in 4,5-Position Amin-Gruppen besitzt. Diese funktionellen Gruppen können an Metallatome/-atome koordinieren oder können chemisch modifiziert werden.The object of the invention is to produce an easily accessible and simple molecule with dithiol and diamino functionality, which is stable under air and room temperature and can also be easily modified.
Unexpectedly, it was discovered that it was possible to produce a molecule that meets these requirements and is stable in air and at room temperature as a solid. The preparation of the molecule does not require much synthetic effort to achieve good yields. It is characterized in that it has thiol groups in the 1,2-position and amine groups in the 4,5-position. These functional groups can coordinate to metal atom(s) or can be chemically modified.
Als besagte Bausteine können Verbindungen mit der allgemeinen Formel (VII) eingesetzt werden.
Wobei R und R' gleich oder unterschiedliche Substituenten der Klassifizierung:
- H-, Alkyl-, Cycloalkyl-, Aryl- oder Heteroarylverbindungen, Heterozyklen, Alkohole, Mercaptane, Amine, Nitrile, Carbonsäuren, Amide, Imide, Hydroxamsäuren, Aminosäuren, Zucker, Ether, Thioether, Ketone, Thioketone, Aldehyde, Thioaldehyde, Ester, Imidine, Amidine, Sulfonsäuren, Sulfoxide, Sulfonamide, Sulfone, Azide, Carbonsäureazide, Peptide, Lactone, Thiolactone oder Halogenide sein können.
- H, alkyl, cycloalkyl, aryl or heteroaryl compounds, heterocycles, alcohols, mercaptans, amines, nitriles, carboxylic acids, amides, imides, hydroxamic acids, amino acids, sugars, ethers, thioethers, ketones, thioketones, aldehydes, thioaldehydes, esters, Imidines, amidines, sulfonic acids, sulfoxides, sulfonamides, sulfones, azides, carboxylic acid azides, peptides, lactones, thiolactones or halides.
Die Erfindung soll anhand der in Formel (VIII) dargestelltem 4,5-Diamino-1,2-benzodithiol näher erläutert werden.
In einem Rundkolben wird Na2S (2.92 g, 22.49 mmol) in 500 mL N2-gesättigtem H2O gelöst. Zu der Lösung wurde nun 4,5-Diamino-1,2-benzodithiocyanat (1 g, 4.5 mmol) geben und unter Rühren mit einem Teflon Magnetrührer für 24 h auf 70 - 80 °C erhitzt. Die erhaltene rote Lösung wurde auf Zimmertemperatur abgekühlt und mit 3 molarer HCl neutralisiert. Der entstandene Niederschlag wurde abfiltriert, mit H2O gewaschen und unter Vakuum getrocknet. Das Produkt wurde als brauner Feststoff (601 mg, 3.49 mmol, 77.55 %) erhalten.Na 2 S (2.92 g, 22.49 mmol) is dissolved in 500 mL N 2 -saturated H 2 O in a round bottom flask. 4,5-Diamino-1,2-benzodithiocyanate (1 g, 4.5 mmol) was then added to the solution and the mixture was heated to 70-80° C. for 24 h while stirring with a Teflon magnetic stirrer. The red solution obtained was cooled to room temperature and neutralized with 3 molar HCl. The resulting precipitate was filtered off, washed with H 2 O and dried under vacuum. The product was obtained as a brown solid (601 mg, 3.49 mmol, 77.55%).
Die neue Verbindung lässt verschiedenste, einfach durchführbare Modifikationen zu. Eine solche wäre z.B. die Reaktion (IX) mit Fe3(CO)12 zur [Fe,Fe]-Hydrogenase:
In einem Schlenkgefäß wurden 200 mg (1.16 mmol) 4,5-Diamino-1,2-benzodithiol und 643 mg (1.28 mmol) Fe3(CO)12 vorgelegt und das Gefäß dreimal evakuiert und dreimal mit trockenem Stickstoff gefüllt. Zu dem Stoffgemisch wurden nun 20 mL THF, welches zuvor getrocknet wurde, und 2 mL N-Methyl-2-pyrrolidon (NMP) geben. Die erhaltene Lösung wurde nun auf 50 °C erhitzt und für 30 min gerührt. Der Reaktionsfortschritt lässt sich mittels Dünnschichtchromatographie überprüfen und nach Ende der Reaktion wurde die Lösung unter Vakuum eingeengt und mittels Säulenchromatographie aufgereinigt. Das Produkt wurde als dunkelroter Feststoff erhalten (404 mg, 0.89 mmol, 77.3 % Ausbeute). Weitere mögliche Reaktionen am Molekül II sind beispielhaft in der Abbildung (X) dargestellt.
ZITATE ENTHALTEN IN DER BESCHREIBUNGQUOTES INCLUDED IN DESCRIPTION
Diese Liste der vom Anmelder aufgeführten Dokumente wurde automatisiert erzeugt und ist ausschließlich zur besseren Information des Lesers aufgenommen. Die Liste ist nicht Bestandteil der deutschen Patent- bzw. Gebrauchsmusteranmeldung. Das DPMA übernimmt keinerlei Haftung für etwaige Fehler oder Auslassungen.This list of the documents cited by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.
Zitierte PatentliteraturPatent Literature Cited
- US 4937321 A [0002]US4937321A [0002]
- WO 2017157782 A1 [0002]WO 2017157782 A1 [0002]
Claims (5)
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DE102021006309.0A DE102021006309A1 (en) | 2021-12-22 | 2021-12-22 | Composition with dithiol and diamino functionality |
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DE102021006309.0A DE102021006309A1 (en) | 2021-12-22 | 2021-12-22 | Composition with dithiol and diamino functionality |
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DE102021006309A1 true DE102021006309A1 (en) | 2023-06-22 |
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DE102021006309.0A Pending DE102021006309A1 (en) | 2021-12-22 | 2021-12-22 | Composition with dithiol and diamino functionality |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4937321A (en) | 1983-10-17 | 1990-06-26 | Hoechst Celanese Corp. | Process for preparing poly((benzo(1,2-D:5,4-D')bisthiazole-2,6-diyl)-1,4-phenylene |
WO2017157782A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
-
2021
- 2021-12-22 DE DE102021006309.0A patent/DE102021006309A1/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4937321A (en) | 1983-10-17 | 1990-06-26 | Hoechst Celanese Corp. | Process for preparing poly((benzo(1,2-D:5,4-D')bisthiazole-2,6-diyl)-1,4-phenylene |
WO2017157782A1 (en) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Organic semiconductors |
Non-Patent Citations (2)
Title |
---|
GRANDOLINI, Giuliano ; MARTANI, Alfio: Trirodanazione della m-fenilendiammina e del triamminobenzolo simmetrico. Sintesi di derivati tiazolici e chetotiazinici dalla diammino- e triammi-notritiofloroglucina. In: Gazetta chimica italiana, Bd. 92, 1962, H. 10, S. 1150-1167. - ISSN 0016-5603. |
WONG, Joanne W. L. [u.a.]: Supramolecular architecture, crystal structure and transport properties of the prototypal oxobenzene-bridged bisdithiazolyl radical conductor. In: Chemical Communications : ChemComm, Bd. 50, 2014, H. 7, S. 785 - 787. - ISSN 1364-548X (E); 0009-241X; 0022-4936; 1359-7345 (P). DOI: 10.1039/c3cc46686h. URL: https://pubs.rsc.org/en/content/articlepdf/2014/cc/c3cc46686h [abgerufen am 2022-02-14]. |
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