ISSN:
0009-2940
Keywords:
6H-1,3,4-Oxadiazin-6-ones
;
1,2-Bismethylenecyclohexane
;
Diels-Alder reactions
;
[1,3,4]Oxadiazino[4,5-b]isoquinolin-1-one derivatives
;
Bicyclo[2.1.1]hexan-5-one, highly substituted
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Cycloadditions of 6H-1,3,4-Oxadiazin-6-ones (4,5-Diaza-α-pyrones), 13[1].-Diels-Alder Reactions with 6H-1,3,4-Oxadiazin-6-ones as Dienophile2,5-Diphenyl-1,3,4-oxadiazin-6-one (1b) reacted as dienophile with 2,3-dimethyl-1,3-butadiene to afford the pyridooxadiazinone 5. Analogously, the oxadiazinoisoquinolines 7c- e were formed on treatment of 2-(4-nitrophenyl)- (1c), 2-(4-tolyl)- (1d), and 2-(4-bromophenyl)-5-phenyloxadiazinone (1e) with 1,2-bis(methylene)cyclohexane (6). In contrast, the methyl oxophenyloxadiazinecarboxylate 1a gave a low yield of the cyclopentenone derivative 8 and 7a in the ratio 2.3:1.0. A third type of product, i.e. the cyclobutanone derivative 9, resulted on exposure of the anisyl(isopropyl)oxadiazinone 1f to 6. The oxadiazinones 1d, e, f have been prepared for the first time. X-ray structure analyses established the identity of the compounds 7d and 9.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260734
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