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1H NMR of the white solid which was obtained after quenching the reaction at -20 °C with ice, warming up to 4 °C over 1 h (in a refrigerator) and filtration of the resulting precipitate on a 0.45 μm glass fiber membrane For leading references on hypervalent iodine(iii) reagents, see:
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It should be noted that a low yield (19%) of compound 12a was obtained using 3 equivalents of cerium ammonium nitrate (CAN) in an acetonitrile-water medium Atom distances: C(6)-O(2): 1.210(3) å; C(8)-O(4): 1.213(3) å; C(10)-O(1): 1.203(4) å; N(3)-H(2): 0.88 å Atom distances: C(6)-O(2): 1.210(3) å; C(8)-O(4): 1.213(3) å; C(10)-O(1): 1.203(4) å; N(3)-H(2): 0.88 å
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When the condensation reaction between 5c and methyl azidoacetate was carried out at 30 °C, an intense degradation of the reaction mixture was observed and no trace of the desired acrylate 13 was isolated
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Oxidation reactions with PIFA were carried out in open vessels, using non-degassed solvents It is noteworthy that the PIFA-mediated (4 equiv) oxidation reaction of dimethoxyazaindoles 2 in methanol-acetonitrile did not lead to the formation of functionalised azaindoles 17
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