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
URL:
http://dx.doi.org/10.1002/jlac.198319830111
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