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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of 4-thia analogues of isoquinoline alkaloids (1989)
    Springer
    Monatshefte für Chemie 120 (1989), S. 463-471 
    Details
    ISSN: 1434-4475
    Keywords: 2H-1,3-Benzothiazines ; 3,4-Dihydro-2H-1,3-benzothiazines ; 4H-1,3-Benzothiazines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Aus 6,7-Dimethoxy-3-methyl-2H-1,3-benzothiaziniumjodid (2) wurde mit Methylmagnesiumjodid (±)-Thiacarnegin (3) dargestellt. Diese Reaktion bietet ein neues Verfahren für die Synthese von 4-substituierten Dihydro-2H-1,3-benzothiazinen.3 wurde auch durch Reduktion von 6,7-Dimethoxy-3,4-dimethyl-2H-1,3-benzothiaziniumjodid (5) erhalten. Die Reduktion der quartären Ammoniumsalze9 a–c ergab ebenfalls die Cryptostillin I-, II-, III-(±)-4-thiaanalogen Verbindungen (10 a–c). Reduktion der 4H-1,3-Benzothiazinium-Salze11 a–c lieferte die entsprechenden Isomeren12 a–c der obengenannten Verbindungen.
    Notes: Summary (±)-4-Thiacarnegin (3) was synthesized by reaction of 6,7-dimethoxy-3-methyl-2H-1,3-benzothiazinium iodide (2) with methyl magnesium iodide, thereby opening a new synthetic route to 4-substituted dihydro-2H-1,3-benzothiazines. Compound3 was also obtained by reduction of 6,7-dimethoxy-3,4-dimethyl-2H-1,3-benzothiazinium iodide (5). In a similar way, reduction of the quaternary salts9 a–c afforded the (±)-4-thia analogues of cryptostilin-I, -II and -III (10 a–c). The isomers of the former compounds (12 a–c) were also synthesized by reduction of the 4H-1,3-benzothiazinium salts11 a–c.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811558
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of partially saturated N-substituted 4H-3,1-benzothiazine-2(1H)-thiones (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 1047-1054 
    Details
    ISSN: 1434-4475
    Keywords: N-Substituted 4H-3,1-benzothiazine-2(1H)-thiones ; Synthesis ; 1H- and13C-spectroscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die säurekatalysierte Reaktion von 2-Arylidencyclohexanonen1 mit N-substituierten Dithiocarbaminsäure2 ergab die offenkettigen Additionsprodukte3 und4. Die Dehydratation von3 und4 führte ausschließlich zu einem der drei möglichen N-substituierten 4H-3,1-Benzothiazin-2(1H)-thion-Isomeren5 und6.
    Notes: Summary Acid-catalyzed reaction of 2-arylidenecyclohexanones1 with N-substituted dithiocarbamic acids2 gave open-chain addition products3 and4. Dehydration of3 and4 afforded only one of the three possible isomeric N-substituted 4H-3,1-benzothiazine-2(1H)-thiones5 and6.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811113
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  • 3
    Electronic Resource
    Electronic Resource
    Stereochemical studies, 73. Saturated heterocycles, 60 (1985)
    Springer
    Monatshefte für Chemie 116 (1985), S. 857-868 
    Details
    ISSN: 1434-4475
    Keywords: 1,1′-Carbonyldiimidazole ; Substituted 1,3-oxazine-2,4-diones with condensed skeleton ; IR ; 1H-NMR ; 3C-NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung cis- undtrans-N-Alkyl-,N-Aralkyl- undN-Aryl-2,4-dioxo-, tri- und tetramethylen-perhydro-1,3-oxazine wurden aus 2-Carboxamido-1-cycloalkanolen und 1,1′-Carbonyldiimidazol dargestellt. Mit Hilfe der IR,1H- und13C-NMR Spektroskopie wurden die Struktur, diecis- odertrans-Annellierung der Ringe und die bevorzugte Konformation der flexiblencis-Isomeren im Vergleich zumcis-trans Isomerenpaar nachgewiesen. Ähnlich zu den früher untersuchten 1,3-Oxazine-2- und -4-onen ist hier ebenfalls das „O-endo“ Konformere bevorzugt; in diesem ist der Sauerstoffaxial angeordnet, und zwar unabhängig von der Zahl der alicyklischen Ringatome und dem flexibleren Oxazindionring.
    Notes: Abstract N-Substituted-2-carboxamido-1-cycloalkanols were cyclized with 1,1′-carbonyldiimidazole to synthesizecis- andtrans-N-alkyl-,N-aralkyl- andN-aryl-2,4-dioxo tri- and tetramethyleneperhydro-1,3-oxazines. The structures of the compounds and theircis ortrans ring anellation were confirmed by IR,1H- and13C-NMR spectroscopy, and thecis andtrans pairs of isomers were compared to establish the predominant conformation of the flexiblecis isomers. It was found that—similarly to the 1,3-oxazin-2- and -4-ones studied earlier—the “O-endo” conformers are preferred, in which the 1-oxygen atom isaxial to the alicyclic ring; this is independent of the number of ring atoms in the alicycle, and of the presence of an oxazinedione ring, even though this is more flexible that the ring of oxazinones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809162
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  • 4
    Electronic Resource
    Electronic Resource
    Book reviews (1991)
    Springer
    Structural chemistry 2 (1991), S. 203-207 
    Details
    ISSN: 1572-9001
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00676633
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  • 5
    Electronic Resource
    Electronic Resource
    Die Herstellung von 5-Imino-3-methyl-1-phenyl-Δ2-pyrazolindithicarbonsäure-(4) und einiger ihrer Derivate (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1155-1158 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of 5-Imino-3-methyl-l-phenyl-2-pyrazolin-4-dithicarboxylic Acid and Some of its DerivativesThe title compound (2) is prepared by reaction of 3-methyl-l-phenyl-2-pyrazol-5-one (1) with carbon disulfide and ammonia. 2 is converted into the methyl (3) and carboxymethyl ester. The i.r. and n.m.r. spectra of 3 are described.
    Notes: Aus 3-Methyl-l-phenyl-Δ2-pyrazolon-(5) (1), Schwefelkohlenstoff und Ammoniak wird die 5-Imino-3-methyl-l-phenyl-Δ2-pyrazolin-dithiocarbonsäure-(4) (2) dargestellt und in den Methyl-(3) bzw. Carboxymethylester übergeführt. Die IR- und NMR-Spektren von 3 werden beschrieben.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040419
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  • 6
    Electronic Resource
    Electronic Resource
    Heterocyclische β-Enamino-ester, IV Zur Reaktion von 2-Amino-3-äthoxycarbonyl-4.5-dihydrofuranen mit Phenylazid und Benz-phenylhydrazid-chlorid (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3510-3518 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic β-Enamino Esters, IV. The Reaction of 2-Amino-3-ethoxycarbonyl-4.5-dihydrofuranes with Phenyl Azide and Benzphenylhydrazide ChlorideHeterocyclic β-enamino esters of the dihydrofurane type (1a, b) react with phenyl azide to give the 5-amino-4-[2-(ethoxycarbonyloxy)alkyl]-1-phenyl-1.2.3-triazoles (4a, b) under ring cleavage and migration of the ester group. Benzphenylhydrazide chloride at first acylates the 2-amino group. After ring cleavage and rearrangement, α-triazolyl-γ-butyrolactones 7a, b are formed, which can be hydrogenated to the diphenyl-triazolyl-1.4-butanedioles 8a, b by the aid of lithiumaluminiumhydride. 1a, b are compared with open chain β-enamino esters with regard to reactivity. I.r. and n.m.r. spectra are described.
    Notes: Die heterocyclischen β-Enamino-ester vom Typ der Dihydrofurane 1a, b reagieren mit Phenylazid unter Ringöffnung und Wanderung der Estergruppe zu 5-Amino-4-[2-äthoxycarbonyloxy-alkyl]-1-phenyl-1.2.3-triazolen (4a, b). Benz-phenylhydrazid-chlorid acyliert zunächst die 2-Ständige Aminogruppe. Nach Ringöffnung und Umlagerung bilden sich α-Triazolyl-γ-butyrolactone 7a, b, die mit Lithiumaluminiumhydrid zu den Diphenyltriazolyl-butandiolen-(1.4) 8a, b hydriert werden. 1a, b werden in ihrer Reaktivität mit offenkettigen β-Enamino-estern verglichen. IR- und NMR-Spektren werden beschrieben.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711041115
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  • 7
    Electronic Resource
    Electronic Resource
    Aromatische Sulfenylchloride, IX. Herstellung, Oxidation und spektroskopische Untersuchung von 1-substituierten (5-Tetrazolyl)aryldisulfiden (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 299-304 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Aromatic Sulfenyl Chlorides, IX. Preparation, Oxidation, and Spectroscopic Investigation of 1-Substituted 5-Tetrazolyl Aryl Disulfides1-Substituted 5-tetrazolyl mesityl disulfides were synthesized which on oxidation with hydrogen peroxide gave disulfide S2, S2-dioxides (thiolsulfonates). The structure of these as well as that of the 1-substituted 5-tetrazolyl p-tolyl disulfide S2, S2-dioxides synthesized earlier was elucidated by means of their i. r. and n. m. r. spectra. The supposed structures have been established by synthesis.
    Notes: Es wurden 1-substituierte (5-Tetrazolyl)mesityldisulfide hergestellt, welche zu Disulfid-S2, S2-dioxiden (Thiosulfonate) oxidiert wurden. Deren Struktur und die der früher hergestellten 1-substituierten (5-Tetrazolyl)p-tolyldisulfid-S2, S2-dioxide wurde anhand ihrer IR- und NMR-Spektren wahrscheinlich gemacht. Die angenommenen Strukturen wurden durch Synthese bewiesen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070135
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  • 8
    Electronic Resource
    Electronic Resource
    Reaktionen von Acetylenketonen, II. Reaktionen von Acetylenketonen mit 1,2-Äthandithiol (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2079-2083 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Acetylenic Ketones, II. Reactions of Acetylenic Ketones with 1,2-Ethanedithiol2 mol 2-R-substituted 1-acetylacetylene (1 und 2) react with 1 mol 1,2-ethanedithiol (3) to yield 1,2-bis(3-oxo-1-butenyl)ethane derivatives of the type 4, 5. Two of them (4b and 5c) react with hydrazine hydrazine hydrate in presence of boron trifluoride etherate to form (1,3-dithiolan-2-yl)acetone azines (6 and 7). The azines can be obtained from the 2-acetonyl-1,3-dithiolanes 8 and 9 formed in the reaction of the appropriate 1 or 2 with 3 (equimolar reactants). The structure of the compounds are elucidated by i. r. and n. m. r. spectroscopy.
    Notes: Bei der Reaktion von 2 Moläquivv. 2-R-substituierter 1-Acetylacetylene (1 und 2) mit 1,2-Äthandithiol (3) bilden sich 1,2-Bis(3-oxo-1-butenyl)äthan-Verbindungen vom Typ 4, 5. Die Umsetzung von 4b und 5c mit Hydrazinhydrat in Gegenwart von Borfluorid-Äthyl ätherat führt zu (1,3-Dithiolan-2-yl)aceton-azinen (6 und 7). Die Azine entstehen auch aus den 2-Acetonyl-1,3-dithillanen (8 und 9), welche in der Reaktion äquimolarer Mengen 1 oder 2 mit 3 gebildet werden. Die Struktur der Produkte wurde IR- und NMR-spektroskopisch bewiesen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070629
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  • 9
    Electronic Resource
    Electronic Resource
    Stereochemische Untersuchungen, 771).  -  Gesättigte Heterocyclen, 641). Synthese von gesättigten Methylen-überbrückten 1,3-Benzoxazinen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3205-3210 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Stereochemical Studies, 771).  -  Saturated Heterocycles, 641). Synthesis of Saturated Methylene-Bridged 1,3-BenzoxazinesThe aminomethylbicyclanol 3, obtained from the cycloadduct 4 of norbornene (1) and trichloroacetyl isocyanate, furnished the 1,3-oxazin-2-one 7, 1,3-oxazine-2-thione 8 and 1,3-oxazines 2a-d. The exo-exo- (10, 12) and endo-endo-1,3-oxazin-4-ones (11, 13) were prepared from the 3-hydroxy-2-carboxamides 5 and 9. Structure of these rigid tricyclic systems were proved by 1H and 13C NMR spectroscopy.
    Notes: Aus dem Cycloaddukt 4 von Norbornen (1) und Trichloracetylisocyanat wurde der Aminoalkohol 3 hergestellt und daraus das tricyclische 1,3-Oxazin-2-on 7, bzw. 1,3-Oxazin-2-thion 8 und die 1,3-Oxazin-Derivate 2a-d synthetisiert. Die mit Norbornan anellierten exo-exo- (10 und 12) bzw. endo-endo-1,3-Oxazin-4-one (11 und 13) wurden aus den 3-Hydroxy-2-carboxamiden 5 und 9 erhalten. Die Struktur der tricyclischen kondensierten Systeme mit starrem Gerüst wurde durch 1H- und 13C-NMR-Spektroskopie bewiesen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171106
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis and Stereochemistry of Stereoisomeric 1,3-Oxazino- and 1,3-Thiazino[4,3-a]isoquinolines (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 803-809 
    Details
    ISSN: 0009-2940
    Keywords: 1,3-Oxazino[4,3-a]isoquinolien / 1,3-Thiazino [4,3-a]isoquinoline / Conformational analysis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from the 6,7-dialkoxy-1-[bis(hydroxymethyl)methyl]-1,2,3,4-tetrahydroisoquinolines 2 and 3, the 4-imino-substituted 1-(hydroxymethyl)-9,10-dialkoxy-2H, 4H-1,6,11b-tetrahydro-1.3-oxazino-and -thiazino [4,3-a]isoquinoline diastereomers 6a-c, 7a-c, 8a-c, 9a-c, 14, and 15 and the 4-substituted 1,6,7,11b-tetrahydro 1,3-oxazino[4,3-a]isoquinoline diastereomers 16-24 were prepared. the relative configurations and the predominant conformation of these products were determined by NMR spectroscopy and for 18 by X-ray diffraction methods. the prepared 1,3-oxazino[4,3-a]isoquinoline diastereomers have predominantly trans conformations (16, 18, 22, 23), whereas cis conformations (cis-A) prevail for 20, 21 and f24. Thus, the first evidence for either trans- or cis-A conformations in 1,3-oxazino[4,3-a] isoquinolines is presented.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230427
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