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  • 1
    Electronic Resource
    Electronic Resource
    New hetero-annelation reactions using N-[bis-(methylthio)-methylene]-amino and related reagents (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 319-324 
    Details
    ISSN: 1434-4475
    Keywords: Fused S,N-heterocycles ; BMMA reagents ; Pyrimidine annelations
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Umsetzung von acyclischen (R 1–3) und cyclischen (R 4–5)BMMA-Reagenzien (BMMA=N-[b is-(Methylthio)-methylen]-amino)mitGewald-artigen Thiophenderivaten (2,3) führte zur Anellierung von Pyrimidinringen. Auf diese Weise konnten linear kondensierte Thiazolo- oder Thiazino- und Pyrrolo-, Pyrido- oder Azepinothiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidine (5 und6) sowie das angulär imidazo-anellierte Thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin8 in guten Ausbeuten auf direkte Weise in Eintopfreaktionen erhalten werden.
    Notes: Summary Reaction of acyclic (B 1–3) and cyclic (R 4–5)BMMA (=N-[b is-(methylthio)-methylene]-amino) reagents withGewald-type thiophene derivatives (2,3) led to annelation of pyrimidine moieties. Thus, linear thiazolo- or thiazino- and pyrrolo-, pyrido- or azepino-fused thiopyrano[4′,3′:4,5]thieno-[2,3-d]pyrimidines (5 and6) as well as the angular imidazo-fused thiopyrano[4′,3′:4,5]thieno-[2,3-d]pyrimidine8 were easily obtained from one-pot reactions in good yields.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00813798
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of new fused heterocycles by annelation of thiopyrano[4′,3′:4,5]thieno[2,3-c]pyrimidines (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 953-959 
    Details
    ISSN: 1434-4475
    Keywords: Fused S,N-heterocycles ; Thieno[2,3-c]thiopyrans ; 1,5,6,8-Tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones ; Thiazolo[3,2-a]thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-5-ones ; 2H,6H,8H-Thiopyrano[4′',3′':4′,5′]thieno[2′,3′:4,5]pyrimido[2,1-b][1,3]thiazin-6-one
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Entsprechend substituierte Thieno[2,3-c]thiopyrane (2, 3, 5, 6, 10, 11) wurden in 1,5,6,8-Tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one (4, 7, 12) umgewandelt, welche als Schlüssel-Zwischenprodukte für Thiazol- und 1,3-Thiazin-Anellierungen zu den tetracyclischen Zielstrukturen7, 8, 9 und13 dienten; diese leiten sich von zwei neuen heterocyclischen Ringsystemen ab.
    Notes: Summary Appropriately substituted thieno[2,3-c]thiopyrans (2, 3, 5, 6, 10, 11) were converted into 1,5,6,8-tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones (4, 7, 12). These in turn were used as key intermediates for annelations of thiazolo and 1,3-thiazino moieties to yield the tetracyclic target structures7, 8, 9, and13, derived from two novel heterocyclic ring systems.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811015
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of dihydrothiopyrano[3,4-c]pyridines and of fusion products thereof (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 945-952 
    Details
    ISSN: 1434-4475
    Keywords: Fused S,N-heterocycles ; Fused S,N,O-heterocycles ; Thiopyrano[3,4-c]pyridine ; Furo[2,3-b]thiopyrano[4,3-d]pyridines ; Thiopyrano[4′',3′':4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Reaktion des 6-Hydroxy-thiopyrano[3,4-c]pyridin-5-carbonsäurenitril — Derivates2 mit α-Halogencarbonylverbindungen führte über die entsprechenden O-substituierten Zwischenprodukte3a–d durch Furan-Anellierungen zu den Furo[2,3-b]thiopyrano[4,3-d]pyridin — Derivaten4a–d. Cyclisierung des entsprechenden Esters4d gab unter Pyrimidin-Anellierung das tetracyclische Produkt8 sowie dessen N-Substitutionsprodukte9a–e. Die Zielverbindungen2–9 leiten sich von den drei neuen heterocyclischen GrundkörpernA–C ab.
    Notes: Summary Reaction of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative2 with α-halogeno-carbonyl compounds gave the O-substituted intermediates3a–d which on treatment with base were converted into the furo[2,3-b]thiopyrano[4,3-d]pyridines4a–d by fusion of a furan moiety. Cyclization of the corresponding ester4d led to fusion of a pyrimidine ring, thus yielding the tetracyclic product8 as well as its N-substituted derivatives9a–e. Target compounds2–9 were derived from the three novel heterocyclic parent systemsA–C.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811014
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of 2′,3′-dideoxynucleosides from 5-alkoxymethyluracils (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 59-70 
    Details
    ISSN: 1434-4475
    Keywords: 2′,3′-Dideoxycytidines ; 2′,3′-Dideoxyuridines ; 5-Alkoxymethyluracils ; Human immunodeficiency virus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Ausgehend vonL-Glutaminsäure (1) wird eine modifizierte Synthese von geschützter 2,3-Dideoxyribose (5) beschrieben. Reaktion von5 mit silyliertem 5-Alkoxymethyluracilen7 b–e in Gegenwart von Trimethylsilyltriflat ergab anomere Mischungen der 2′,3′-Dideoxyuridinderivate8 a–e und9 a–e. Abspaltung der Schutzgruppe mit methanolischen Ammoniak und chromatographische Trennung ergab die entsprechenden Nucleoside10 a–e und11 a–e. Behandlung von9 b–e mit Tri(1H-1,2,4-triazol-1-yl)phosphinoxid und nachfolgende Reaktion von12 b–e mit Ammoniak in Dioxan ergab die Cytosinderivate13 b–e, welche nach Behandlung mit methanolischem Ammoniak die entsprechenden 2′,3′-Dideoxycytidinderivate14 b–e und15 b–e ergaben. Im Gegensatz zur Stammverbindung hatten diese Alkoxymethylderivate keine nennenswerte Wirksamkeit gegen den menschlichen Immunschwächevirus (HIV-1).
    Notes: Summary A modified synthesis of protected 2,3-dideoxyribose5 starting fromL-glutamic acid (1) is described. Reaction of5 with silylated 5-hydroxymethyluracil7 a and 5-alkoxymethyluracils7 b–e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2′,3′-dideoxyuridine derivatives8 a–e and9 a–e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides10 a–e and11 a–e. Treatment of9 b–e with tri(1H-1,2,4-triazol-1-yl)phosphine oxide and subsequent reaction of12 b–e with ammonia in dioxane afforded the cytosine derivatives13 b–e which on treatment with methanolic ammonia gave the corresponding 2′,3′-dideoxycytidine derivatives14 b–e and15 b–e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00815166
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