Science of Synthesis

Larsen, R. D.; Cai, D., Science of Synthesis, (2005) 15, 400.

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]

‌Meeeee 88‌ Meeeeeäeeee Meeeeeeee eeee Meeee Meeeee[‌888‌,‌888‌]

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Meeeee 8-(Meeeeeeee)eeeeeeeee-8-eeeeeeeeeee (‌88‌, M8 = M8 = M; M8 = MMe; M8 = MM8Me); ­Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeeeeeeeee ee eeeeeeeeeee eeeeeee eee eeee eee ee eeeee.

M eeee ee 8-eeeeeeeeeeeeeeeee (‌88‌, M8 = M8 = M; 8 eeeee) eee eeeee 8-(eeeeeeeee)-8-(eeee­eeeeeeee)eeeeeeeeee (‌88‌, M8 = MMe; M8 = MM8Me; M8 = Me; 8 eeeee) ee eee MeMM (88 eM•eeee−8 ee eee eeeeeeeeeeee) eee eeeeeee eeee eeeee MMM (eeeeeee, 8 eeeee) eee eee eeeeeeeee eeeeeee eee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeee, eeeeee eeee M8M, eee eeeeeeeee ee eM 8 eeee eee eeeeeeee ee 8 M MMe. Mee eeeeeee eeee eee eeeeeeeee eeee MeMMe, eee eee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eeeeeeeeee eee eeeeeeeeee eeee eeeeee eeeeeeeee ee eeeeee. Meeeeeeeeeee, eee eeeee eeee eee eeeeeeeee eeee eee eeeeee eeeee. Mee eeeee eeee eee eeeeeeeee ee MM8Me8 (88 eM·88 eeee−8) eee eeeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 (88 eM·88 eeee−8), Me8MM (8 eeeee eeeee ee eee eeeee), eee MeM (8 eeeee eeeee ee eee eeeee), eee eee eeeeeee eee eeeeeee ee 88°M eee 88 e. Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeeeee eee eeeeeeeee ee e eeeeeeeee eee; eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.