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43
-
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31544444903
-
-
note
-
In this study, 2,3-dimethylbutadiene was selected as a (symmetric) model diene. Application of other (asymmetric) dienes is currently part of our research.
-
-
-
-
44
-
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0033613776
-
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31544450939
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46
-
-
31544463988
-
-
note
-
-1, in agreement with the spectral properties of methyl (Z/E)-2-nitro-3-phenylprop-2-enoate.
-
-
-
-
47
-
-
31544475346
-
-
note
-
Although this cycloaddition can be carried out at atmospheric pressure in refluxing toluene, the use of high pressure was preferred in view of shorter reaction times, higher yields, avoiding high temperatures, stirring, and the use of large excesses of 2,3-dimethylbutadiene. Comparison of high pressure versus reflux conditions: 4-methoxybenzyl (E/Z)-2-nitro-3-phenyl-2-propenoate reacted with 2,3-dimethylbutadiene and yielded 73% of the cycloadduct after 48 h of reflux in toluene. At 15 kbar, the same cycloadduct was obtained in 86% after 16 h at room temperature.
-
-
-
-
48
-
-
0038700605
-
-
2O (recently reported by Willert, M.; Benito, J. M.; Meldal, M. J. Comb. Chem. 2003, 5, 91-101) resulted in a slight improvement of the yield.
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-
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Willert, M.1
Benito, J.M.2
Meldal, M.3
-
49
-
-
31544466457
-
-
note
-
Cyclization attempts with triethylamine (in tetrahydrofuran or ethylene glycol dimethyl ether) or sodium hydride in tetrahydrofuran failed. The stereochemistry of one of the diastereomers of hydantoin 18 was confirmed with X-ray analysis.
-
-
-
-
50
-
-
31544440072
-
-
note
-
The reported yield is after six reaction steps and is based on an initial loading of the hydroxymethylene resin of 1.0-2.0 mmol/g.
-
-
-
-
51
-
-
31544462542
-
-
note
-
In principle, this matrix might be extended into a third dimension by application of a series of dienes; however, for the synthesis of the library as described in this report, just one diene was used.
-
-
-
-
52
-
-
31544473335
-
-
note
-
1 position were unsuccessful. There are indications that the Knoevenagel reaction merely failed using imines with these substituents (according to IR and gravimetrical analysis).
-
-
-
-
53
-
-
31544453538
-
-
note
-
+ signal of the Boc-deprotected derivative was dominant in the LC/MS analysis.
-
-
-
-
54
-
-
31544462001
-
-
note
-
6.
-
-
-
-
55
-
-
31544455182
-
-
note
-
Derivatives with 2′-, 3′-, or 4′-pyridyl substituents either were not formed or were formed in very low yields and purities when following the described synthetic route; unpublished results.
-
-
-
-
58
-
-
85010450312
-
-
For a review on synthesis and application of nitroacetic acid and its esters, see: Shipchandler, M. T. Synthesis 1979, 666-682.
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Shipchandler, M.T.1
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31544460877
-
-
note
-
Acts as a radical scavenger to avoid diene polymerization.
-
-
-
-
60
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-
0000019934
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