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  • 1
    Electronic Resource
    Electronic Resource
    Zur Reaktion von cyclischen Ketonen mit Thioharnstoff bzw. Ammonrhodanid Über Heterocyclen, 24. Mitt. (1970)
    Springer
    Monatshefte für Chemie 101 (1970), S. 1686-1695 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Cyclic ketones have been found to react with thiourea or ammonium thiocyanate according to reaction conditions to give derivatives of dihydro-2(1H)-pyrimidinthione or dihydro-4(3H)-pyrimidinthione, resp.
    Notes: Zusammenfassung Cyclische Ketone reagieren mit Thioharnstoff bzw. Ammonrhodanid je nach den eingehaltenen Bedingungen zu Abkömmlingen des Dihydro-2(1H)-pyrimidinthions bzw. Dihydro-4(3H)-pyrimidinthions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01152082
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  • 2
    Electronic Resource
    Electronic Resource
    Über Dihydro-3-thioxo-3H-1,2-dithiolo[4,3-d]pyrimidin-5(4H)-one und Dihydro-3H-1,2-dithiolo[4,3-d]pyrimidin-3,5(4H)-dithione Über Heterocyclen, 34. Mitt. (1973)
    Springer
    Monatshefte für Chemie 104 (1973), S. 585-597 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Dihydro-3-thioxo-3H-1,2-dithiolo[4,3-d]pyrimidin-5(4H)-one (2) geben bei Methylierung 4-Methylderivate (2) bzw. Tetrahydro-3-methylthio-5-oxodithiolopyrimidiniumsalze (6); aus den Dithionen (3) entstehen 5-Methylthio-bzw.5-Methylthio-4-methylderivate (4) bzw. Tetrahydro-3-methylthio-5-thioxodithiolopyrimidiniumsalze (6). Peressigsäure führt2 in das Tetrahydrodithiolopyrimidiniumhydrogensulfat (10) über.2 bzw.3 geben mit Phenylhydrazin 3-Phenylhydrazone; Tetrahydro-3-methylthiodithiolopyrimidiniumjodide (6) reagieren mit Aminen bei Anwesenheit vonHMPT zu den 3-Iminoverbindungen.10 gibt mit Methylketonen und Wasserstoffakzeptoren 3-Acylmethylendihydrodithiolopyrimidin-5(4H)-one.
    Notes: Abstract Dihydro-3-thioxo-3H-1.2-dithiolo[4.3-d]pyrimidine-5(4H)-ones (2) give on methylation 4-methylderivatives (2) and tetrahydro-3-methylthio-5-oxodithiolopyrimidinium salts (6) resp.; from dithiones (3) arise 5-methylthio-resp. 5-methylthio-4-methylderivatives (4) resp. tetrahydro-3-methylthio-5-thioxo-dithiolopyrimidinium salts (6). Peracetic acid converts2 to tetrahydrodithiolopyrimidinium hydrogensulphate10. 2 and3, resp. give with phenylhydrazine 3-phenylhydrazones. Tetrahydro-3-methylthiodithiolopyrimidiniumiodides (6) react with amines in presence ofHMPT to 3-iminocompounds.10 gives with methyl ketones and hydrogen acceptors 3-acylmethylendihydro-dithiolopyrimidine-5(4H)-ones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00903126
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  • 3
    Electronic Resource
    Electronic Resource
    Zur Synthese der 4-Dialkylamino-5,6-dihydro-2(1H)-pyridinthione sowie entsprechender 4-Alkylamino- bzw. 4-Arylaminoverbindungen (1976)
    Springer
    Monatshefte für Chemie 107 (1976), S. 1361-1367 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The rearrangement of 1-alkyl- and 1-aryldihydro-6-methyl-2(1H)-pyrimidinethiones (1 a) or-ones (1 b) and of methylene compounds (2a, 2b) resp., to 4-alkylamino- and 4-arylaminodihydro-2(1H)-pyridinethiones (4 a) or-ones (4 b) takes place via the corresponding 3-alkylamino- and 3-aryl-amino-3-butenylisothiocyanates (3 a) or-isocyanates (3 b). Dialkylamino-dihydro-2(1H)-pyridinethiones (10) are formed by heating dihydro-6-methyl-2(1H)-pyrimidinethiones (6 a) and 3,4-dihydro-6-methyl-1,3-thiazin-2-thiones (6 b) with dialkylformamides and by the reaction of secondary amines with tetrahydro-6-hydroxy-6-methyl-1,3-thiazin-2-thiones (5 a), with N,N-dialkyl-N′-(3-oxobutyl)-thioureas (7) and 3-oxobutyl isothiocyanates (8). A general method for the preparation of10 is the reaction of dialkylammoniumrhodanides12, N,N-dialkylthioureas13 and dialkylammonium chlorides and KCNS, resp., with 3-alken-2-ones14 and 4-hydroxy-2-alkanones15, resp. Methyl ketones such as acetone, which readily undergo the aldol condensation, behave analogously. The reactions described take place via the intermediate aminoalkenyl isothiocyanates (9).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01153915
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  • 4
    Electronic Resource
    Electronic Resource
    Zur Umsetzung des 3,4,5,6-Tetrahydro-6-hydroxy-4,4,6-trimethyl-1,3-thiazin-2-thions mit sekundären Aminen (1977)
    Springer
    Monatshefte für Chemie 108 (1977), S. 243-255 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Tetrahydro-6-hydroxy-trimethyl-1,3-thiazine-2-thione (1) reacts with secondary amines via the dialkylammonium-3-oxoalkyldithiocarbamate3, either via isothiocyanates6 to 4-dialkylaminodihydro-2(1H)-pyridinethiones7 or to dialkylammonium dithiocarbamates (13), depending on the amine used and the reaction conditions. Subsequently, 6-dialkylaminotetrahydro-1,3-thiazine-2-thiones11 or tetrahydro-6-mercapto-1,3-thiazine-2-thione10 are formed. On being heated to reflux,11 reacts to pyridinethione7 and 4-dialkylaminodihydrothiopyranthione19. With secondary amines only13 is formed from tetrahydro-6-hydroxytetramethyl-1,3-thiazine-2-thione20. The reaction of dihydrotrimethyl-1,3-thiazine-2-thione21 with secondary amines leads to N,N-dialkylthioureas16 or dialkylammonium thiocyanates17 and with dialkylformamides 4-dialkylaminodihydropyridinethiones7 are formed. Dihydrotetramethyl-1,3-thiazine-2-thione24 reacts neither with secondary amines nor with dialkylformamides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00900928
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  • 5
    Electronic Resource
    Electronic Resource
    Zur Umsetzung des 3,4,5,6-Tetrahydro-6-hydroxy-4,4,6-trimethyl-1,3-thiazin-2-thions mit primären Aminen (1977)
    Springer
    Monatshefte für Chemie 108 (1977), S. 257-263 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Tetrahydro-6-hydroxy-4,4,6-trimethyl-1,3-thiazine-2-thione (1 a) reacts with methyl-, ethyl- and n-butylamine to the corresponding 1-alkyl-6-alkylaminotetrahydro-2(1H)-pyrimidinethione12 but withi-propylamine to tetrahydro-6-isopropylamino-1,3-thiazine-2-thione (6 d). On treatment withDCC,6 d is rearranged to dihydro-4-isopropylamino-2(1H)-pyridinethione (8 d), and 6-amino-tetrahydro-1,3-thiazinethione (6 a) to dihydro-4,4,6-trimethyl-2(1H)-pyrimidinethione (10 a). The reaction of 6-aminothiazinethiones6 a, d and 6-(4-morpholinyl)-thiazinethione13 resp., with methylamine leads to 1-methyl-6-methylamino-pyridinethione12 b. 1-Alkyl-6-alkylamino-tetrahydro-2(1H)-pyrimidinethiones (12) react at reflux temperature to dihydro-1-alkylpyrimidinethiones10. With methylamine only 6-methylamino-3,4,4,6-tetramethyl-1,3-thiazine-2-thione (6 f) is formed from tetrahydro-6-hydroxy-tetramethyl-1,3-thiazine-2-thione (1 b).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00900929
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  • 6
    Electronic Resource
    Electronic Resource
    Über 2,3-Dihydro-4(1H)-pyrimidinone (1977)
    Springer
    Monatshefte für Chemie 108 (1977), S. 381-386 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Cyclic ketones react with β-aminocrotonamide in inert solvents to 4-methyl-1,5-diazaspiroalken-2-ones (4 a, 4 b, 4 c, resp.). The structure of the compounds is confirmed by their reactivity as well as by their UV, IR, NMR and mass spectra.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00901990
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  • 7
    Electronic Resource
    Electronic Resource
    Über die Bromierung von substituierten 3,4-Dihydro- und 6-Hydroxy- bzw. 6-Äthoxy-3,4,5,6-tetrahydro-2(1H)-pyrimidinonen (1975)
    Springer
    Monatshefte für Chemie 106 (1975), S. 407-416 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Bromination of 1-benzyl-4-methyl-3.4-dihydro-2(1H)-pyrimidinone (9 a) with 1 mole Br2 in CHCl3 yields 1-benzyl-5-bromo-6-hydroxy-4-methyltetrahydro-2(1H)-pyrimidinone,12 a, or the 6-ethoxypyrimidinone13 a, according to whether H2O orEtOH is used in working up. With 2 moles Br2,9 a analogously affords the 5.5-dibromopyrimidinnes14 a or15 a. Bromination of the 6-hydroxypyrimidinone10 a yields the same products,12 a and13 a, or14 a and15 a respectively, while the 4-phenyl-pyrimidinones9 b and11 b yield the corresponding 5-bromo-and 5.5-dibromopyrimidinones13 b and15 b. The structures of the compounds12 a-15 b are confirmed by their NMR data and chemical properties: the oxopyrimidinylmethylureas16 a and17 a are formed by the action of methylurea on12 a and13 a, or on14 a and15 a respectively; with hexamethylenetetramine,12 a reacts to give the 5.6-dihydroxypyrimidinone18 a, while13 b is transformed to the 4-phenylpyrimidinone19 b. 13 b was also synthesized from α-bromocinnamaldehyde. The mechanism of bromination is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01150521
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  • 8
    Electronic Resource
    Electronic Resource
    Über das Tetrahydrospiro [cyclohexan-1,2′(1′H)-chinazolin]-4′(3′H)-on (1970)
    Springer
    Monatshefte für Chemie 101 (1970), S. 1547-1558 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The product obtained by heating cyclohexanone with urea has been found to be 5′. 6′. 7′. 8′-tetrahydrospiro[cyclohexane-1.2′(1′H)-quinazoline]-4′(3′H)-one, not cyclohexylidene-2-carbamoylcyclohex-1-enylamine, as was previously assumed1. Compounds with analogous structures were formed by heating cyclopentanone or cycloheptanone with urea. Characteristic features of this class of compounds, i.e. β-carbamoyl enamines, are the enhanced reactivities of the nuclear 4 a′-position and of the methylene group in the peri-position to NH-1′.
    Notes: Zusammenfassung Das beim Erhitzen von Cyclohexanon und Harnstoff entstehende Produkt ist nicht als Cyclohexyliden-2-carbamylcyclohex-1-enylamin, sondern als 5′, 6′, 7′, 8′-Tetrahydrospiro-[cyclohexan-1,2′(1′H)-chinazolin]-4′(3′H)-on zu formulieren1. Analog gebaute Verbindungen bilden sich aus Cyclopentanon bzw. Cycloheptanon und Harnstoff. Die genannten Kondensate sind als cyclische β-Carbamylenamine aufzufassen; charakteristisch sind die Reaktivität der zur NH-Gruppe/1′, in peri-Stellung befindlichen CH2-Gruppe bzw. der Kernstelle 4a′.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00911421
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  • 9
    Electronic Resource
    Electronic Resource
    Über Heterocyclen, 3. Mitt.: Zur Reaktion von Homologen des Acetaldehyds mit Carbamiden (1961)
    Springer
    Monatshefte für Chemie 92 (1961), S. 79-87 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Zusammenfassung Auch bei Einwirkung von Propionaldehyd und Butyraldehyd auf Carbamide im sauren Medium ist die Bildung von 2-Oxo-6-ureido-hexahydropyrimidinen und z. T. von 2,7-Dioxo-dekahydro-pyrimido [4,5-d]pyrimidinen zu beobachten. Valeraldehyd und höhere Homologe reagieren hingegen bei Anwesenheit von Mineralsäuren nicht mehr mit Carbamiden zu cyclischen Verbindungen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00914071
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  • 10
    Electronic Resource
    Electronic Resource
    Über Heterocyclen, 4. Mitt.: Über β-Ureidoaldehydacetale (1961)
    Springer
    Monatshefte für Chemie 92 (1961), S. 278-291 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Zusammenfassung 2-Oxo-6-ureidohexahydropyrimidine und 2-Oxo-6-hydroxyphenylhexahydropyrimidine können durch Einwirkung von Carbamiden bzw. Phenolen auf β-Ureidoaldehyde und β-Ureidoaldehydacetale gewonnen werden. Aus dem β-(1-Methylureido)-butyraldehyd-diäthylacetal bildet sich im sauren Medium ein Hexahydropyrimidyl-tetrahydropyrimidin, dessen Struktur aufgeklärt wurde.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01153882
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