ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Syntheses of Heterocyclic Compounds, CCV. - Reactions of Cyclic Oxalyl Compounds, XX. - Reactions of 4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione with Aliphatic NitrilesThe reaction of 4-benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dione (1) with butyro-. isobutyro-, and phenylacetonitrile under thermolysis conditions leads via the dibenzoylketene-intermediate 2 to the 2-alkyl-5-benzoyl-6-phenyl-1,3-oxazin-4-ones 3, which can be converted by hydrolysis into the N-acylacrylamides 4. 2-Benzoyl-3-phenyl-5,6-dihydro-1 H-pyrano[2,3-c]isoquinoline-1,6-dione (5) is formed as a by-product in the reaction of 1 and phenylacetolnitrile. The structure of 5 is confirmed by alkylation and oxidation reactions.
Notes:
4-Benzoyl-5-phenyl-2,3-dihydrofuran-2,3-dion (1) reagiert mit Butyro-, Isobutyro- und Phenylacetonitril unter Thermolysebedingungen über die Dibenzoylketen-Zwischenstufe 2 zu den 2-Alkyl-5-benzoyl-6-phenyl-1,3-oxazin-4-onen 3, die sich zu den N-Acylacrylsäureamiden 4 hydrolysieren lassen. Aus 1 und Phenylactonitril entsteht als Nebenprodukt 2-Benzoyl-3-phenyl-5,6-dihydro-1 H-pyrano[2,3-c]isochinolin-1,6-dion (5), dessen Struktur durch Alkylierung sowie Oxidation mit KMnO4 gesichert wurde.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197719771022
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