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  • 1
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie von 1,2,4-Oxadiazolen mit C-5-Heteroatom-Bindung, II. Synthese von 5,6-Dihydro-4H-1,2,4-oxadiazinen durch Ringerweiterung von Δ2-1,2,4-Oxadiazolin-5-onen (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 1911-1923 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,2,4-Oxadiazoles containing a C-5-heteroatom Bond, II Synthesis of 5,6-Dihydro-4H-1,2,4-Oxadiazines by ring Extention of Δ2-1,2,4-oxadiazolin-5-onesN-(2-Hydroxyalkyl)-, and N-(3-chloro-2-hydroxypropyl)-Δ2-1,2,4-oxadiazolin-5-one derivatives (6, 8), prepared by reaction of Δ2-1,2,4-oxadiazolin-5-ones (4) with alkylene oxides or epichlorohydrine, respectively, are used as starting materials for the synthesis of 5,6-dihydro-4H-1,2,4-oxadiazines (2) as well as for that of N-monosubstituted amidoximes (7, 11). The reactivity of 2 with methyl iodide and acylating agents is reported.
    Notes: Die durch Reaktion der Δ2-1,2,4-Oxadiazolin-5-one 4 mit Epoxiden bzw. Epichlorhydrin hergestellten N-(2-Hydroxyalkyl)- bzw. N-(3-Chlor-2-hydroxypropyl)-Derivate 6, 8 werden bei der Synthese von 5,6-Dihydro-4H-1,2,4-oxadiazinen (2) bzw. der N-monosubstituierten Amidoxime 7, 11 als Ausgangsmaterialien eingesetzt. Die Reaktionsfähigkeit von 2 gegenüber Methyljodid und Acylierungsmitteln wird beschrieben.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080614
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  • 2
    Electronic Resource
    Electronic Resource
    Untersuchungen über Verbindungen mit Berban-Gerüst, IV. Über die Herstellung von halogenierten Despyrroloyohimbon-Derivaten mit prostaglandinartiger und prostaglandin-antagonistischer Wirkung (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3390-3403 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigation on the Chemistry of Berbans, IVSynthesis of Halogen Containing Depyrroloyohimbon Derivatives with PG-like and PG-antagonistic EffectHalogenation of depyrroloyohimbon derivatives of different configurations (1a-d, 2a-c, 3a-c) was investigated in order to obtain useful intermediates for the synthesis of depyrroloreserpines. The isomerisation of the primer products (9a-e, 10b and 11a, c, e) to γ-bromo derivatives (9f-j, 10g and 11f, h, j) was also studied.
    Notes: Die Halogenierung von Despyrroloyohimbon-Derivaten verschiedener Konfiguration (1a-d, 2a-c, 3a-c) wurde untersucht, um brauchbare Intermediärprodukte zur Synthese von Despyrroloreserpinen zu gewinnen. Die Isomerisierung von Primärprodukten (9a-e, 10b und 11a, c, e) zu γ-Brom-Derivaten (9f-j, 10g und 11f, h, j) wurde studiert.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091017
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  • 3
    Electronic Resource
    Electronic Resource
    Chemistry of the Heterocyclic Pseudobasic Amino Alcohols, XXXVIII Ring-Chain Tautomerism of Pyrimido[6,1-a]isoquinolines (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 493-498 
    Details
    ISSN: 0009-2940
    Keywords: Pyrimido[6,1-a]isoquinolines / Pseudobases, heterocyclic / Ring-chain tautomerism ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In basis media, 4-substituted pyrimido[6,1-a]isoquinolin-2-imine hydrochlorides (4) constitute an equilibrium system involving the tautomeric forms characteristic of pseudobases 5, 6, 7 and the anhydro base 9. In aqueous solution in the pH range 7-13 the ammonium hydroxide form 5 is present. Between pH 13 and 14 the pseudobase 6 probably arises from this by covalent binding of the hydroxy group. 6 is then converted to the more stable imino type anhydrobase 9. Ring cleavage of 4 by excess alkali or of 9 by a small amount of water gives 1-(acylamidinomethylen)isoquinolines 7. Compounds 7 and 9 are stable in the solid state or in aprotic solutions but revert to cation 5 in dilute protic solutions.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230315
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese von 4-Aminopyrimidinen aus 1,2,4-Oxadiazolen, I. Eine neue, allgemeine Methode zur Herstellung von 4-Aminochinazolinen und deren Heteroanaloga (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3183-3193 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, I. A Novel General Method for the Preparation of 4-Aminoquinazolines and their Hetero AnaloguesCatalytic hydrogenation of 3-(2-aminoaryl)-1,2,4-oxadiazoles (9, 12, 15, 18, 21) to 2-amino-N-acylarenecarboxamidines (10, 13, 16, 19, 22) followed by dehydration gave condensed 4-aminopyrimidines (11, 14, 17, 20, 23), while the corresponding secondary amines (24) afforded 1,2-disubstituted 4-iminoquinazolines (26). Reduction and dehydration of 3-[2-(acylamino)phenyl]-1,2,4-oxadiazoles (28) provided, via a somewhat different pathway, 4-(acylamino)quinazolines (31).
    Notes: Katalytische Hydrierung von 3-(2-Aminoaryl)-1,2,4-oxadiazolen (9, 12, 15, 18, 21) zu 2-Amino-N-acylarencarboxamidinen (10, 13, 16, 19, 22) und nachfolgende Dehydratisierung ergab kondensierte 4-Aminopyrimidine (11, 14, 17, 20, 23), während die entsprechenden sekundären Amine (24) zu 1,2-disubstituierten 4-Iminochinazolinen (26) führten. Reduktion und Dehydratisierung der 3-[2-(Acylamino)phenyl]-1,2,4-oxadiazole 28 lieferte auf einem von dem vorangehenden teilweise verschiedenen Reaktionsweg die 4-(Acylamino)chinazoline 31.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171104
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, II A General Method for the Preparation of 4-Substituted 6,7-Dihydro-9,10-dialkoxy-2H-pyrimido[6,1-a]isoquinolin-2-imine Hydrochlorides (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1039-1043 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Während die Reduktion von 5′-substituierten 1-[(1,2,4-Oxadiazol-3-yl)methyl]-3,4-dihydroisochinolinen (7) mit NaBH4 selektiv zu den entsprechenden Tetrahydroisochinolinen 8 und durch nachfolgende Ringisomerisierung zu Pyrazolo[5,1-a]isochinolinen 9 führte4), ergab die katalytische Hydrierung von 7 in Anwesenheit von Chlorwasserstoff durch reduktive Spaltung der N-O-Bindung des 1,2,4-Oxadiazolringes und nachfolgende spontane Dehydratisierung ganz allgemein 4-substituierte Pyrimido[6,1a]isochinolin-2-imin-hydrochloride (11).
    Notes: 5′-Substituted 1-[(1,2,4-oxadiazol-3-yl)methyl]-3,4-dihydroisoquinolines (7) were reduced by NaBH4selectively to give the corresponding tetrahydroisoquinolines (8) which underwent ring isomerization to pyrazolo[5,1-a]isoquinolines (9). Catalytic hydrogenation of 7 in the presence of hydrogen chloride, in turn, gave by reductive cleavage of the N-O bond of the 1,2,4-oxadiazole ring and subsequent dehydration, quite generally, 4-substituted pyrimido[6,1-a]isoquinolin-2-imine hydrochlorides (11).
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200625
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  • 6
    Electronic Resource
    Electronic Resource
    Ring Transformation of 1,2-Disubstituted 4(1H)-Quinazolone Oximes to 3,5-Disubstituted 1,2,4-Oxadiazoles (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 1107-1112 
    Details
    ISSN: 0009-2940
    Keywords: ANRORC mechanism ; 1,2,4-Oxadiazoles ; 4(1H)-Quinazolone oximes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ringumwandlung von 1,2-disubstituierten 4(1H)-Chinazolonoximen zu 3,5-disubstituierten 1,2,4-OxadiazolenO-Benzoyl- und O-Acetyl-2-benzylaminobenzamidoxim (8b, c) ergeben in basischem Medium 5-substituierte 3-(2-benzylaminophenyl)-1,2,4-oxadiazole (9a, b), während Erhitzen in reinem Wasser zu 2-Amino-1-benzylbenzimidazol (10) führt. Reaktion von 2-(N-Acylbenzylamino)benzonitril (12) mit Hydroxylamin, oder Behandlung von O-Acyl-2-(N-benzoylbenzylamino)benzamidoxim (8f, g) with Säure ergibt die neuen 1,2-disubstituierten 4(1H)-Chinazolonoxime 13, die beim Erwärmen in Gegenwart von Alkali nach einem ANRORC-Mechanismus zu den 1,2,4-Oxadiazolen 9a, b isomerisieren.
    Notes: In basic media O-Benzoyl- and O-acetyl-2-benzylaminobenzamide oxime (8b, c) give 5-substituted 3-(2-benzylaminophenyl)-1,2,4-oxadiazoles (9a, b), while on heating in pure water 2-amino-1-benzylbenzimidazole (10) is formed. Reaction of 2-(N-acylbenzylamino)benzonitrile (12) with hydroxylamine, or treatment of O-acyl-2-(N-benzoylbenzylamino)benzamide oximes (8f, g) with acid give the novel 1,2-disubstituted 4(1H)-quinazolone oximes 13, which isomerize on heating with alkali by an ANRORC mechanism to the 1,2,4-oxadiazoles 9a, b.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220616
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, III A Novel Type of Formation of Olefins from Amines (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 111-113 
    Details
    ISSN: 0009-2940
    Keywords: Olefin formation ; Pyrimido[6,1-α]isoquinolines ; 4-Aminopyrimidines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On heating at 100°C, 1,2,3,4-tetrahydro-6,7-dialkoxy-1-[(acylamidino)methylene]isoquinolines (5) are transformed into 4-substituted 6,7-dihydro-9,10-dialkoxy-2H-pyrimido[6,1-α]isoquinoline-2-imines (6), while at 140°C they undergo a novel prototropic rearrangement via 6 to give 4-amino-6-(4,5-dialkoxy-2-vinylphenyl)-2-phenylpyrimidines (7). The structure of 7a has been determined by X-ray analysis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240119
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  • 8
    Electronic Resource
    Electronic Resource
    Ring-Chain Tautomerism of 3,5-Disubstituted 5,6,7,8-Tetrahydro-3H-3H-[1,2,4]oxadiazolo[4,3-c]pyrimidine, a Novel Heterocyclic Ring System (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2065-2070 
    Details
    ISSN: 0009-2940
    Keywords: Ring-chain tautomerism ; 3H-[1,2,4]-Oxadiazolo[4,3-c]pyrimidine, 5,6,7,8-tetrahydro- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 3-aminopropionamide oxime (7) with two equiv. of benzaldehyde or of a substituted benzaldehyde gives cis-3,5-diaryl-5,6,7,8-tetrahydro-3H[1,2,4]oxadiazolo[4,3-c]-pyrimidines (cis-11a-c,e). According to 1H-, 13C-, and 15N-NMR studies these compounds form in solution a novel triple tautomeric equilibrium comprising cis- and trans-11a-c, e and 3-[2-(benzylidineamino)ethyl]-5-aryl-4,5-dihydro-1,2,4-oxaliazoles (10a-c, e). However, the solid obtained from 7 and two equiv. of cinnamaldehyde proved to be an imine (10g), which again formed in solution a similar triple tautomeric system analogously to the mutarotation of sugars. The structure of 11a and 10g was confirmed by X-ray crystallography.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240931
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, V[1]. Reductive Formation of 2-(Benzoylamino)indole from 3-(2-Aminobenzyl)-5-phenyl-1,2,4-oxadiazole and Its Transformation to 6-Phenyl-8H-pyrimido-[1,6-a: 4,5-b']diindole, a New Heterocyclic Ring System (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1835-1841 
    Details
    ISSN: 0009-2940
    Keywords: 1,2,4-Oxadiazoles, 5-substituted, 3-(2-aminobenzyl)- ; Indoles, 2-(acylamino)- ; 8H-Pyrimido[1,6-a: 4,5-b']diindoles, 6-aryl ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Catalytic hydrogenation of 5-substituted 3-(2-aminobenzyl)-1,2,4-oxadiazoles 7 give 2-(acylamino)indoles 10. Treatment of 2-(benzoylamino)indoles 10a-c with acid leads to the novel 6-phenyl-8H-pyrimido[1,6-a: 4,5-b']diindoles 19a-c. A route for the new ring formation is proposed. Catalytic hydrogenation of 19a (Raney nickel, 70°C, atmospheric pressure) saturates the 6-phenyl ring but leaves the pentacyclic ring system intact. The structure of 19a is confirmed by an X-ray crystallographic analysis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260814
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of novel HMG-CoA reductase inhibitors, II. Heterocyclic analogs of mevinolin (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1877-1883 
    Details
    ISSN: 0947-3440
    Keywords: HMG-CoA reductase inhibitors ; 3-Indolylheptanoates and -acetates ; 4-Chromanylheptanoates and -acetates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The indole (1) and chroman analogs (2) of mevinolin and their 6S diastereomers 15c and 25d were synthesized in several steps starting with methyl (R)-3-[(tert-butyldimethylsilyl)oxy]-4-formylbutyrate (12) and 2-(indol-3-yl)ethanol (3) or 6-methoxychroman-4-one (16), respectively. Compounds 1 and 2 inhibited moderately the HMG-CoA reductase. The diastereomers 15c and 25d were shown to be inactive.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199510263
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