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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and antiviral evaluation of quinazoline, thieno-[2,3-d]pyrimidine, and lumazine analogues of 3′-fluoro-3′-deoxythymidine (FLT) (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1371-1375 
    Details
    ISSN: 0947-3440
    Keywords: Nucleosides ; HIV ; 3′-Fluoronucleosides ; FLT analogues ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,4(1H,3H)-Quinazolinediones 3a-c, lumazine (3d) and thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8) were silylated and condensed with methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (2) by using trimethylsilyl triflate as a catalyst to afford the corresponding cyclic nucleosides 4 and 9 and acyclic nucleosides 5 and 10. Removal of the protecting group from the glycon moiety was achieved in good yields by treatment with sodium methoxide in methanol at room temperature. The new FLT analogues were devoid of activity against HIV-1 and HSV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507183
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  • 2
    Electronic Resource
    Electronic Resource
    Phosphorus pentoxide in organic synthesis, VII. Synthesis of 3-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-imines (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 2066-2072 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphorpentoxid in der Organischen Synthese, VII. - Synthese von 3-Aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-iminenDurch Umsetzung von 2-(Acetylamino)-3-pyrrolcarbonitrilen 1 mit einer Mischung von Phosphorpentoxid, N,N-Dimethylcyclohexanamin und einem geeigneten Arylamin-hydrochlorid bei 150-180 °C werden die Titelverbindungen 2 erhalten. Das verwendete Arylamin-hydrochlorid muß absolut wasserfrei sein, da anderenfalls 4-(Arylamino)pyrrolo[2,3-d]pyrimidine 4 als Nebenprodukte entstehen können. - Die Ergebnisse der Prüfung auf Pestizid- und Antikrebs-Wirksamkeit werden mitgeteilt.
    Notes: The title compounds 2 were prepared by treating 2-(acetylamino)-3-pyrrolecarbonitriles 1 with a mixture of phosphorus pentoxide, N,N-dimethylcyclohexanamine, and an appropriate arylamine hydrochloride at 150-180°C. The importance of using absolutely anhydrous arylamine hydrochlorides is stressed because failing this, 4-(arylamino)pyrrolo[2,3-d]pyrimidines 4 can be formed as by-products. - The results from pesticide and anticancer screenings are reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319831203
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  • 3
    Electronic Resource
    Electronic Resource
    Phosphorus Pentoxide in Organic Synthesis, XII. Synthesis of 7H-Pyrrolo[2,3-d]pyrimidin-4-amines (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 142-148 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphorpentoxid in der Organischen Synthese, XII.  -  Synthese von 7H-Pyrrolo[2,3-d]-pyrimidin-4-aminenEs wird ein einstufiges Verfahren zur Herstellung einiger neuer substituierter 7H-Pyrrolo[2,3-d]-pyrimidin-4-amine 2 beschrieben. Dazu werden die entsprechenden Pyrrolo[2,3-d]pyrimidin-4(3H)-one 1 in einer Mischung aus Phosphorpentoxid, N,N-Dimethylcyclohexylamin und dem geeigneten Amin-hydrochlorid erhitzt. Bei Hydrochloriden aromatischer Amine verläft die Reaktion glatt bei 200-220°C innerhalb von 1-4h, Hydrochloride aliphatischer Amine hingegen reagieren langsamer und liefern die Produkte 3 in geringer Ausbeute. Im Fall von Diethylamin-hydrochlorid wird zusammen mit dem erwarteten Produkt 3e das dimere Kondensationsprodukt 5 isoliert. Ferner werden die Ergebnisse von Pestizid-Eignungstests mitgeteilt.
    Notes: A one-step synthesis for the preparation of a new series of substituted 7H-pyrrolo[2,3-d]pyrimidin-4-amines 2 is described. The method consists in heating the corresponding pyrrolo [2,3-d]pyrimidin-4(3H)-ones 1 in a mixture of phosphorus pentoxide, N,N-dimethylcyclohexylamine, and the appropriate amine hydrochloride. With aromatic amine hydrochlorides the reaction proceeds smoothly at 200-220°C for 1-4 h, whereas with aliphatic amine hydrochlorides, the reaction takes place at slower rate affording the products 3 in lower yields. With diethylamine hydrochloride, the condensed dimeric product 5 is isolated together with the expected product 3e. The results from pesticide screenings are reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850115
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  • 4
    Electronic Resource
    Electronic Resource
    Phosphorus Pentoxide in Organic Synthesis, XVI. A One-step Synthesis of 2-Methyl-N6-aryladenines from 5-Acetylamino-1H-imidazole-4-carboxamide Hydrochloride (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 921-928 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Phosphorpentoxid in der Organischen Synthese, XVI1). - Eine Eintopf-Synthese von 2-Methyl-N6-aryladeninen aus 5-Acetylamino-1H-imidazol-4-carboxamid-hydrochlorid2-Methyl-6-(arylamino)purine 3 lassen sich aus 5-Amino-1H-imidazol-4-carboxamid-hydrochlorid über 5-Acetylamino-1H-imidazol-4-carboxamid-hydrochlorid (1) durch Erhitzen (180°C) mit Phosphorpentoxid, Triethylamin-hydrochlorid und einem geeignet substituierten Anilin herstellen.
    Notes: 5-Amino-1H-imidazole-4-carboxamide hydrochloride has been converted into a series of 2-methyl-6-(arylamino)purines 3 via 5-acetylamino-1H-imidazole-4-carboxamide hydrochloride (1) which was heated with phosphorus pentoxide, triethylamine hydrochloride, and an appropriate substituted aniline at 180°C.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850506
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  • 5
    Electronic Resource
    Electronic Resource
    Diphosphorus pentaoxide in organic synthesis, XXVII. A one-step synthesis of thiazolo[5,4-d]pyrimidin-7-amines and purine-6-thiones from 5-(acylamino)-2-methyl-4-thiazolecarboxamides (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1255-1261 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Diphosphorepentaoxid in der organischen Synthese, XXVII. - Eine Einschritt-Synthese von Thiazolo[5,4-d]pyrimidin-7-aminen und Purin-6-thionen aus 5-(Acylamino)-2-methyl-4-thiazolcarboxamiden5-(Acylamino)-2-methyl-4-thiazolcarboxamide 1 wurden in eine Reihe von N-Arylthiazolo-[5,4-d]pyrimidin-7-aminen 2 und 9-Aryl-1,9-dihydro-6H-purin-6-thione 3 übergeführt, indem man sie mit einer Mischung aus Diphosphorpentaoxid, Triethylamin-hydrochlorid und einem geeigneten, substituierten Anilin 2 min auf 240°C und dann 1 h auf 160°C erhitzte. Das Verhältnis von 2 zu 3 ist abhängig vom eingesetzten Anilin und Thiazol.
    Notes: 5-(Acylamino)-2-methyl-4-thiazolecarboxamides 1 have been converted into a series of N-arylthiazolo[5,4-d]pyrimidin-7-amines 2 and 9-aryl-1,9-dihydro-6H-purine-6-thiones 3 by heating in a mixture of diphosphorus pentaoxide, triethylamine hydrochloride, and an appropriate substituted aniline at 240°C for 2 min and then at 160°C for 1 h. The ratio of 2 and 3 depends on the aniline and thiazole used.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860711
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  • 6
    Electronic Resource
    Electronic Resource
    Anomalously coupled nucleosides, I tributylammonium phosphates in chloroform for direct coupling of 2-deoxy-D-ribose with N6-substituted adenines (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1837-1846 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ungewöhnlich verknüpfte Nucleoside, I. - Tributylammonium-phosphate in Chloroform zur direkten Verknüpfung von 2-Desoxy-D-ribose mit N6-substituierten AdeninenPhosphorpentoxid reagiert mit Wasser und Tributylamin in Chloroform zu einer homogenen Lösung von Tributylammonium-phosphat, Pyrophosphat und Trimetaphosphat. 3-(9-Adenyl)-2,3-didesoxy-D-threo-pentofuranosen 3 fallen kristallin an, wenn 2-Desoxy-D-ribose (2) mit N6-substituierten Adeninen 1 in dieser Lösung 7 Tage bei 40°C umgesetzt wird.
    Notes: Phosphorus pentoxide reacts with water and tributylamine in chloroform to give a homogeneous solution of tributylammonium phosphate, pyrophosphate, and trimetaphosphate. 3-(9-Adenyl)-2,3-dideoxy-D-threo-pentopyranoses 3 precipitate on treatment of 2-deoxy-D-ribose (2) with N6-substituted adenines 1 in this solution at 40°C after 7 days.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619861103
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  • 7
    Electronic Resource
    Electronic Resource
    Anomalously Coupled Nucleosides, II. Reaction of 3-[N6-(4-Chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranose with Alcohols and Anilines (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 705-708 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ungewöhnlich verknüpfte Nucleoside, II. - Reaktion von 3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranose mit Alkoholen und Anilinen3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranose (1) wurde in die Alkyl-3-[N6-(4-chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranoside 2 und die N-Aryl-3-[N6-(4-chlorphenyl)-2-methyl-9-adenyl]-2,3-didesoxy-D-threo-pentopyranosylamine 4 umgewandelt. Die Verbindungen 2 wurden als α/β-Anomeren-Gemische isoliert, bei verlängerten Reaktionszeiten wurden jedoch reine α-Anomere 3 erhalten.
    Notes: 3-[N6-(4-Chlorphenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranose (1) has been converted into the alkyl 3-[N6-(4-chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranosides 2 and into the N-aryl-3-[N6-(4-chlorophenyl)-2-methyl-9-adenyl]-2,3-dideoxy-D-threo-pentopyranosylamines 4. The compounds 2 were isolated as mixtures of α and β anomers whereas pure α anomers 3 could be obtained after prolonged reaction times.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870812
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  • 8
    Electronic Resource
    Electronic Resource
    Nitriles in Heterocyclic Synthesis: A Novel Synthesis of 2-Amino-3-pyrrolecarbonitriles (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1145-1146 
    Details
    ISSN: 0170-2041
    Keywords: 3-Pyrrolecarbonitriles, 2-amino- ; Malononitriles, phenylacyl ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Amino-3-pyrrolecarbonitriles are prepared by the reaction of phenacylmalononitrile with primary aromatic amines using a catalytical amount of concd. HCl.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890285
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  • 9
    Electronic Resource
    Electronic Resource
    A short route to 3′-deoxy-3′-fluorothymidine (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 1137-1139 
    Details
    ISSN: 0170-2041
    Keywords: Fluorination ; Thymidine, 3′-deoxy-3′-fluoro- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 5-OH-protected methyl glycosides 2 and 3 were epimerized to give the corresponding epimers 6 and 7 via an oxidation-reduction procedure. Reaction of 6 with diethylamino-sulfur trifluoride (DAST) afforded the fluoro sugar 8, which was coupled with thymine to give 3′-deoxy-3′-fluorothymidine (12) after deprotection with saturated ammonia in methanol.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001206
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of Uridine with Methylene-2-thiohydantoin as 5-Substituent (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 619-621 
    Details
    ISSN: 0170-2041
    Keywords: Uridine, methylene-2-thiohydantoin derivative ; Nucleosides ; 2-Thiohydantoin ; Herpes simplex virus ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 5-Formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)uracil (4) was synthesized from 5-formyluracil (2) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (3) and condensed with 2-thiohydantoin derivatives 5 by using piperidine as the catalyst to give 5-(uridin-5-ylmethylene)-2-thiohydantoin (8a) and 3-phenyl-5-(uridin-5-ylmethylene)-2-thiohydantoin (8b) after deprotection with sodium methoxide in methanol. Compound 8a was also obtained in an inversed reaction sequence from 5-formyluracil starting with condensation with 2-thiohydantoin and then with 3. The compounds 8a and 8b did not show any activity against HSV-1 or HIV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940613
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