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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 107-111 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Chemistry of the Amino Oximes, XVI. The Properties of 2-Pyrimidone N-Oxide DerivativesBy reaction of anti-β-amino ketoximes 1a-d with phosgene, 2-pyrimidone N-oxide derivatives 2a-d are formed as intermediates which react in different ways. By tautomerisation of 2a the 3,6-dihydro-3-hydroxy-2(1H-pyrimidinone derivative 3a and by addition of water to 2b the 3,4,5,6-tetrahydro-3,4-dihydroxy-2(1H)-pyrimidinone 3b is formed. 1,3-Dipolar cycloaddition of the 2-pyrimidone N-oxide 2c to the tautomeric ene-hydroxylamine 3c yields the spiro compound 4. By [3 + 3] cycloaddition of the N-oxide 2d the pentacyclic ring system 6 is formed
    Notes: Aus den anti-β-Amino-ketoximen 1a-d entstehen mit Phosgen intermediär die 2-Pyrimidon-N-oxid-Derivate 2a-d, die unterschiedlich weiterreagieren. Durch Tautomerie bildet sich aus 2a das 3,6-Dihydro-3-hydroxy-2(1H)-pyrimidinon 3a, durch Addition von Wasser an 2b das 3,4,5,6-Tetrahydro-3,4-dihydroxy-2(1H)-pyrimidinon 3b. Aus dem 2-Pyrimidon-N-oxid 2c und seinem tautomeren En-hydroxylamin 3c entsteht durch [3+2]-Cycloaddition die Spiroverbindung 4 und aus dem N-Oxid 2d durch [3+3]-Cycloaddition das pentacyclische System 6.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 2223-2230 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Chemistry of Amino Oximes, XV1).  -  Synthesis of 1,2,5,6-Tetrahydropyrimidine 3-Oxide Derivativesβ-Benzylamino oximes 1a  -  e were prepared by Mannich reaction and converted into anti-amino oximes 2a  -  c. By reaction with aldehydes, 1,2,5,6-tetrahydropyrimidine 3-oxides 3a  -  h were prepared. The N-oxides cyclize with dimethyl acetylenedicarboxylate to give 3a,4,6,7-tetrahydro-5H-isoxazolo[2,3-c]pyrimidine derivatives 4a, b, and g.
    Notes: Die β-Benzylaminoketone 1a  -  e wurden mittels der Mannich-Reaktion synthetisiert und daraus die anti-Amino-oxime 2a  -  e hergestellt. Die Umsetzung mit Aldehyden führt zu 1,2,5,6-Tetrahydropyrimidin-3-oxiden 3a  -  h. Durch Cycloaddition mit Acetylendicarbonsäure-dimethylester entstehen 3a,4,6,7-Tetrahydro-5H-isoxazolo[2,3-c]pyrimidin-Derivate 4a, b und g.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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