ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Oxazolones, III . - The Transformation of 4-Oxazolin-2-ones into 1-(2-0xoalkyl)-1,3,5-tri-azine-2,4,6(1H,3H,SH)-triones and vice versaN-Phenyl(2-oxo-4-oxazolin-3-carbox)amides 2a- c are converted into 1 -(2-oxoalkyl)-3,5-di- phenyl-l,3,5-triazine-2,4,6(lH,3H.5H)-triones 4 on reaction with phenyl isocyanate. The reaction is catalysed by potassium cyanate and presumably proceeds via N-(2-oxo-4- oxazolin-3-ylcarbonyl)-N,N′-diphenylurea derivatives 3. Tris(2-oxoalkyl)-l,3,5-triazine-2,4,6 (lH,3H,SH)-triones 6 can be synthesized from trisodium 1,3,5-triazinetriolate (5) and %-halo- ketones. Sonie of the compounds 4 and 6 rearrange into 4-oxazolin-2-ones 1 at elevated temperature in the presence of potassium cyanate.
Notes:
N-Phenyl(2-oxo-4-oxazolin-3-carbox)amide 2a- c reagieren mit Phenylisocyanat zu 1 -(∼-OXO- alkyl)-3,5-diphenyl-1,3,5-triazin-2,4,6(lH,3H,5H)-trionen 4. Die Reaktion wird durch Kaliumcyanat katalysiert und verläuft vermutlich über N-(2-Oxo-4-oxazolin-3-ylcarbonyl)- N,N′-diphenylharnstoffderivate 3. Tris(2-oxoalkyl)-l,3,5-triazin-2,4,6-(IW,3N,5∼)-trione 6 sind aus Trinatrium-l,3,5-triazintriolat (5) und a-Halogenketonen zugänglich. Einige der Produkte 4 und 6 lagern sich bei höherer Temperatur und in Gegenwart von Kaliumcyanat in 4-Oxazolin-2-one 1 um.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197619760735
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