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15.3.1.1.1.3.2.1.2 Variation 2: Oximino Derivatives of Aldehydes and Ketones

DOI: 10.1055/sos-SD-015-00689

Larsen, R. D.; Cai, D.Science of Synthesis, (200515400.

In some cases, aldehydes or ketones do not react well under the Friedländer conditions. One means around this problem is to use the oxime derivative of the carbonyl compound. Methazonic acid, the dimer of nitromethane, is used extensively to prepare 3-nitroquinolines.[‌125‌,‌127‌,‌128‌] This is particularly a good route for preparing quinolin-3-amines. The dilithiooxime of oxime 45 (R4=Ph; R6=H) is useful for preparing 2,4-diarylquinolines 46 with 2-aminobenzophenones 44 (R2=Ph) (Scheme 16).[‌129‌,‌130‌] The O-methyloxime of benzyl­oxypyruvate 45 (R3=OBn; R4=CO2Et; R5=Me) is an effective substrate for the synthesis of 3-hydroxyquinoline-2-carboxylates.[‌131‌]

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