ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
The Chemistry of Amino Oximes, XIII. 3,6-Dihydro-2(1H)-pyrazinone 4-OxidesThe 3,6-Dihydro-2(1H)-pyrazinone 4-oxides 3a-c were prepared by cyclisation of anti-α-(chloroacetylamino)ketoximes 2a-c. From 3 with PCl3 the 3,6-Dihydro-2(1H)-pyrazinones 5a and b were formed. Cycloaddition of 3 with dimethyl acetylenedicarboxylate yields the 4,5,6,7-tetrahydro-6-oxo-3aH-isoxazolo[2,3-a]pyrazines 6a-c, which tautomerise to the enols, anti-1-(Chloroacetylamino)-1-phenyl-2-propanone oxime (2d) cyclises to 5-methyl-6-phenyl-2(1H) pyrazinone (4d).
Notes:
Die 3,6-Dihydro-2(1H)-pyrazinon-4-oxide 3a-c wurden durch Ringschluß der anti-α-(Chloracetylamino)ketoxime 2a-c erhalten. Mit PCl3 entstehen aus 3 die 3,6-Dihydro-2(1H)-pyrazinone 5a und b und durch Cycloaddition mit Acetylendicarbonsäure-dimethylester die 4,5,6,7-Tetra-hydro-6-oxo-3aH-isoxazolo[2,3-a]pyrazin-Derivate 6a-c, die zum Enol tautomerisieren. anti-1-(Chloracetylamino)-1-phenyl-2-propanon-oxim (2d) cyclisiert zu 5-Methyl-6-phenyl-2(1H)-pyrazinon (4d).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19811140718
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