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The absence of a carbonyl group could favor peri-substitution by decreasing the steric hindrance in particular, this factor could be essential for annulated six- and seven-membered heterocycles, Thus, the latest data show that reaction of 3-acetyl-2-methyl-5,7-dinitroquinoline with PhSH results in selective peri-substitution: Mezhnev, V. V, Dutov, M. D, Sapozhnikov, O. Yu, Kachala, V. V, Shevelev, S. A. Mendeleev Commun. 2007, 234. For more detailed discussion, see Supporting Information
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The absence of a carbonyl group could favor peri-substitution by decreasing the steric hindrance (in particular, this factor could be essential for annulated six- and seven-membered heterocycles). Thus, the latest data show that reaction of 3-acetyl-2-methyl-5,7-dinitroquinoline with PhSH results in selective peri-substitution: Mezhnev, V. V.; Dutov, M. D.; Sapozhnikov, O. Yu.; Kachala, V. V.; Shevelev, S. A. Mendeleev Commun. 2007, 234. For more detailed discussion, see Supporting Information.
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In the 1H NMR spectrum of 3, signals of 2-acetylamino-4,6-dinitrobenzoic acid are present, evidently due to hydrolysis of 3 in water-containing DMSO-d6. This instability of 2-methylbenz[d][1,3]oxazine-4-ones (which leads, in particular, to the problems with NMR spectra interpretation) is well known: Rocco, S. A, Barbarini, J. E, Rittner, R. Synthesis 2004, 429 and references cited therein
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6. This instability of 2-methylbenz[d][1,3]oxazine-4-ones (which leads, in particular, to the problems with NMR spectra interpretation) is well known: Rocco, S. A.; Barbarini, J. E.; Rittner, R. Synthesis 2004, 429 and references cited therein.
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