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15.9.1.1.1.1 Method 1: Acridines from 2-Aminophenylcarbonyl Compounds and Phenols

DOI: 10.1055/sos-SD-015-01674

Prager, R. H.; Williams, C. M.Science of Synthesis, (200515988.

This procedure, also known as the von Niementowski reaction,[‌23‌] can be regarded as a variation of the Pfitzinger procedure, in which a 2-aminobenzaldehyde is condensed with a phenol. 2-Aminobenzaldehydes react with phloroglucinol (benzene-1,3,5-triol) under physiological conditions at pH 8 and room temperature to give acridine-1,3-diols such as 2 in yields of up to 90% (Scheme 3).[‌24‌] No general procedure appears to be available: these conditions give only minute yields with benzene-1,2,3,5-tetrol, whereas high yields of the corresponding acridine are obtained on heating.

Meeeee 8 Meeeeeee-8,8-eeee eeee 8-Meeeeeeeeeeeeeeee eee Meeeeeeeeeeeee[‌88‌]

Me 8888, Meeeeeeeee[‌88‌] eeeeeeee eeee, eeeee eeeeeeee eeeeeeeeee, eeeeee (8, 8M-eeeeee-8,8-eeeee) ee eeeeeeeeee ee e 8-eeeeeeeeeeeeeeeee eeeeeeeeee, eeeee eeeeee eee eeeeeeeee ee e eeeeeee eeeee ee eee 8-eeeeeeee ee eee eeeeeeee eeeeeee, eeeeeeeee eeeeeee-eeeeeeeeeee eeeeeeeee 8. Mee eeee eeeeeeee ee eeeeeeee eeeee eeeeeee eeeeee eeeeeeeeee.[‌88‌] Meee eeeeeeee eee eeeeeeeee ee Meeee 8 (e.e., eee eeeeeeeee ee 88). Meeeeeee eee eeee eeeeee eeeeeeee eeeeeeeee e eeeeeeeeeeeee eeeee ee eeeee- ee eeeeeeeeeeeeeee-8-eeeeeeeeeeee, eee eeeeeeee ee eeeeee eeee eeeeeeeeeeeeee ee 88°M eeeee eeee eeeeee ee 8,8-eeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee. Meeeeeeeee eeeeeeee eeeeee eeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeee (Meeeee 8).[‌88‌] Meeeee, eeeeeeeeeeee, eee 8-eeeeeeeeeeeee ee eee eeeee eeee eeeeee. Mee eeeeeeee eeeeeeee eeeeeeeeee eeeeeeeeee eeee eee eeee ee eeeeeeeeeee ee eeeeeee eeeeee ee eeee eeeeeee ee eeeeeeeee,[‌88‌] ee ee eeeeeeeee ee eeeee eeeeee ee eeeeeeee,[‌88‌] eee eeeee eeeeeeee eee ee eeeeeee ee eee eee ee eeeeee eeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeee eeee Meeeeee eee Meeeeee[‌88‌]

M eeeeeee ee eeee eeeeeeeee eeeeeeee eee eeeeeeee ee M-eeeeeeeeeee, eeeee eeee eeee eeeeeeeee eeeee eeeeeeee eeeeeeeeee.[‌88‌‌88‌] Meee, eeee M-eeeeeeeeeeee (88) ee eeeeeeeee ee eeeeeeee eeeeeeeeee, eeeeeeee-8-eeeeeeeeee eeee (88) ee eeeeeeee, eee eeeeeeeee eeeeeeeeeeeeeee ee eeeeeee eeeeeee (Meeeee 8).

Meeeee 8 Meeeeeee-8-eeeeeeeeee Meee eeee M-Meeeeeeeeeee[‌88‌]

Me eeeeeeeeeee ee eee eeeeeeee ee eeeeee eeee eeeeeee ee eee eeeeeeee ee (8-eeeeeeeeeee)-(eee)eeeeee eeee eeee eeeeeeeeeee-8,8-eeeee eeeeeee, eeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeee ee 88% eeeee.[‌88‌]

Mee Meeeeeäeeee eeeeeeee,[‌88‌] eeeeeeee ee 8888,[‌88‌] ee eeeeeeeee e eeeeeeeee eeeeeeeee eeee ee eeeeee eeeeeee ee eee eeeeeeeee ee eeeeeee- eee eeeeeeeeeeeeeeeeeee. Mee eeeeee eee eeeeeeeeee eeeeeeeeee eeeeee eeeeeee eeeeee. Me eeeeeee eee eeeeeeee eeee eeeeeeee­eee ee eeeeeeeeeeeeeee, eeeeeeeee eeee ee 88 eee eeeeeeee eeeeeeee (Meeeee 8).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee ee eee Meeeeeäeeee Meeeeeee[‌88‌,‌88‌]

Meeeeeee eeee 8-eeeeeeeeeeeee eeeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeee, 8-eeeee­eeeeeeeeeeeee, eee 8-eeeeeeeeeeeeeeeeee. Meeee-eeeee eee eeeeee-eeeee eeeeeeeeeee eee eeeeeee eeeeeeee eeee eee eeeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeee. Mee eeeeeeee eee eeeeeee eeeeeee e eeeeeeee, eee eeeeeeeee eeeeeeee eee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeee ee eee eeeeeeee[‌88‌] eee eeeeeee eee eeeeeeee ee ee eeee ee eeee.[‌88‌] Meeeeeeeeee eeeeeeeee eeeeeee eeee eeeeee eeeeeeeeee,[‌88‌] ee eeee ee eeeeeee e eeeeeeeeeee eeee.[‌88‌] Meee-eeeeeeeee Meeeeeäeeee eeeeeeeee eee eeee eeee eeeee eeee eee eeee-eeeeeeeee eeeeeeeee; eeeeee eeee eeeeeeeee eeeeeee eeeeeeeeeeee eeee, eeeeeeee eeee, 8-eeeeeeeeeeeeeee eeee, eee eeeeeeeeeeeeee eeee.

M eeeeee ee eeeeeeeeeeeee eeee eeee eeee ee eee Meeeeeäeeee eeeeeeee; eeeee eee eeeeeeeee eeeee. Meee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee ee eee Meeeeeäeeee eeeeeeee eee eeeeeeee ee Meeee 8.

Meeee 8 Meeeeeeee eeee 8-Meeeeeeeeeeeeeeeeee Meeeeeeee[‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌‌88‌]

Meeeeeeee Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee
(%)
Mee
MMM/MeMM, eeeeee, 88eee M8MM8,MMM, eeeeee, 88e 8888 [‌88‌][‌88‌]
ee MeMM [‌88‌]
ee MeMM [‌88‌]
MeMM MeMM, eeeeee, 8e 88 [‌88‌]
888°M 88 [‌88‌]
888°M, 8e 88 [‌88‌]
MeMe/M8MM8 MMM, eeeeee 8888 [‌88‌,‌88‌]
MMM MMMM, 888°M, 8e 88 [‌88‌]
MMM MMMM, 888°M, 88e 88 [‌88‌]
MeMM, eeeeee, 8e eeeee [‌88‌]

Meeeeeeeee Meeeeeäeeee eeeeeeeeeeee ee eeeeeee eeeeee eeee eeeeeeeeee eeeee eeeeeee ee eeeeeeee eeee eeeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeeeee.[‌88‌] Meee eeeeee eee eeeee eeeeeee eee (eee Meeee 8 eee eeeeeeeeeeeeee eeeeeeee), eee eee eeee eeeeeee ee eeeeee eeeeeeeeeee eeeeeeeeeee. Meeeeeeee eeeee eeeeeeeeeeee eee eeee eeeeeeee ee eeee eeeeeeee: eee eeeeeee, eeeeeeeeeeeeeeeeeeeeee 88 eeeee eeee 8-eeeeeeeeeeeeeeeee eeeee eee eeeee eeeeeeeeee ee eeee 88M-eeeeeeeeeeee 88 eeeee eeeeee eeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee 88M-Meeeeeeeeeee[‌88‌]

Mee eee ee eeeee eeeeeeeeeeeeee ee eee Meeeeeäeeee eeeeeeee eeeeeeeeeee eeeeeeeeee eee eeee eee eeeee eeeeee eeeeeeeeee ee eeeee eee eeeeeeee. Meeeeeeeeeeeee eeeeeeeeeeeeee eeeee eeeeeeeeeeeeee ee eee eeee-eeeeeeee eeeeee-eeeeeeeee eeeeee (eee Meeee 8). Mee eeeeeee, eee eeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeee eeeeeeeeeeeee (88) eeeee eee eeeeeeeeeeeeeeeeee 88 ee eee eeee eeeeeee (Meeeee 8).[‌88‌] Mee eeeeeeee ee 8,8-eeeeeeeeeeeeeeeee-8(8M)-eee (88) eeee 8-eeeeeeeeeeeeeeeee eeeeeeeeeeeee (88) eeeeeee eeee eee eeeeeee eeeeeeeeeee[e]eeeeeeee eeeeee 88.[‌88‌] Meeeeeeeeeeeeee ee eee eeee­[e]eeeeeeee 88 eee ee eeeeeeeeeee,[‌88‌] ee eee ee eeeeeeee ee eee eeeeeee eeeeeeee ee Meeeeee 88.8.8.8.

Meeeee 8 Meeeeeeeeeeeee eeee Meeeeeeeeeeeeeeee Meeeeeeeeeeee[‌88‌,‌88‌]

α-Meeeeeeee, e.e. eeeeeeeeeee-8,8-eeeee, eeeee eeee 8 eeeeeeeeeee ee 8-eeeeeeeeeeeeee­eee ee eeee eeeeeeeeeeee eeee ee 88 (Meeeee 8).[‌88‌] Meeeeeeeeeeee (eeeeeeeeeeeeeee) ee eee eeeeeee[‌88‌] ee eeeeeeeeee[‌88‌] eeeeeeeeeee eee eeeeee ee eeeeeeee ee eeeee eeeeeeeee/eeeeeeee, eee, eeeeee, ee eeeeee.

Meeeee 8 Meeeeeeeeeeeee eeee α-Meeeeeeee[‌88‌]

8-Meeeeeeeeeeeeeeeee eee eeeeee eee eeeeee eeeeeee eeeeeeeeee eeee eee ee eeeeeeeee eeee eeeeeee-8-eeeeee ee eeee ee eeeeeeeee eeeeeee eeeeee, eeeee eeeeeeeeeeeeeee ee eee eeeeeee eeeeeee. Meee eeeeee eee eeee eeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeee eeeeee eeeeeeeeeee.[‌88‌]

Meeeeeee 8-eeeeeeeeeeeeee eeeeeeee eeeeee eeeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeeeee (eee Meeeeee 88.88), eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee eeeee M,M-eeeeeeeeeeeeeeeeeeeeeeeee-8-eeeeee ee eee eeee. Meee eeeeee, eee-eeee eeeeeeeee eee eeee eeee ee eeeeeee eeeeee ee e eeee eeeee ee eeeeeeeee ee eee ee eee eeeeeeeee eeeeeeeeeeeeeeeeeee.[‌88‌]

Mee Meeeeee eeeeeeeee ee eeeeeeeee ee eeeeee ee Meeeeee 88.88.8.8.8.8. 8-Meeeeeeeeeeeeeee (e.e., 88) eeeee eeeeeee eeee eeeeeeee ee eeee 8-eeeeeeeeeee eeeeeeeee (e.e., 88), eeeeeeeeee eee eeeeeeeeeeee 8-eeeeeeeeee(eeeeee)eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeee Meeeeeeee ee Meeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeee-8-eeeeeeeeee Meee (8, M8=M); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeeee (88e, 88eeee) eee eeeee ee e eeee ee eeeeee (8e, 88eeee) eee MMM (8e, 88eeee) ee eee eeeeeee eeeeee ee M8M. Mee eeeeeee eee eeeeeeee eee 8e, eee eeeeee eeee M8M. Meeeeeeeeeeee eeee eee MMe eeee e eeeeee-eeeee eeeeeee; eeeee: 8.8e (88%); ee >888°M (eee).

Mee eeeeeeeeeeeeee, ee MeMM eee eeee ee eeeeeee, eee eeeeee eee eeeeeeeee eee 8e ee eeee 8,8-eeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee; eeeee: eeeee; ee >888°M (eee eeee eeeeeeeeeeeeeee).

Meee[e]eeeeeee-8-ee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeee eeeeeeee 8-eeeeeeeeeeeeeeeee (8.8e, 88eeee) eee eeeeeeeeeee-8,8-eeee (8.8e, 88eeee) ee 8% ee MeMM (88eM) eeeeeeeeee e eeeeee MeMM eee eeeeeeee eee 8e, eeee eeeeeeeee eeee MeMM. Mee eeeeee eeeeeeeeeee eee eeeeeeeee, eeeeee eeee M8M, eee eeeeeeeeeeeeee (MMM) ee eeee eee eeeeeee; eeeee: 8.8e (88%); ee 888888°M.

8,8,8,88-Meeeeeeeeeee-88-eeeeee-8,8-eeeeeeeeeee[e]eeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

8-Meeee-8,8-eeeeeeeeeeeeeeeeeeeee (8.8e, 8.8eeee) eee eeeeeeeee ee eeeee MM8Me8 (88eM), eee 8M MMe ee Me8M eee eeeee eeee eeeeeeee eeeeeeee ee ee. Mee eeeeeee eee eeee eeeeeee, eee eee eeeeeeeeeeee eeeeeeeeeeeeeeeee eeeeeeeeeeeee eeee eee eeeee eee 8e eeeee eeee eeeeee. Mee eee MMe eeee eee eeeeeeeeee eeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee (8.88e, 8.88eeee), eee eee eeeeeee eee eeeeeeeeeee eeee e eeeeee eeee eee eeeeee ee 888°M eee 8e. Mee eeeeeeeee eeeee eeee eee eeeeeeeee ee eeeeeee MeMM (888eM), eeeeeeeeeeee ee 888eM, eee eeee eeeeeeeee. Mee eeeeeee eee eeeeeeeee eee eeeeee eeee eeeeeee (8×8eM) ee eeee eeeeee eeeeeee ee eee eeeeeeeeeee[e]eeeeeeee eeeeeeeeeeeee; eeeee: 8.88e (88%).

Mee MMe eeee eee eeeeeeeeeee ee eeeeeee MeMM (888eM) eee, ee eeeeeee, eeeee ee MM8MM eee eeeee eeeeeeee ee eeeeee eee eM ee 88. Mee eeeeeeeee eeeee eeeeee eeeeeeeeeee eeeeeeeeee eee eeeeeee eeee M8M (888eM) eee eeeeeeeee eeee MM8Me8 (8×888eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeee ee eeee eee eeee eeee; ee 888°M.

8-Meeee-8,8-eeeeeeeeeeeeee-8(8M)-eee (8); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeeeee ee 8-eeeeeeeeeeeeeeeee (888.8e, 8.88eee) ee eeeeeee (8M) eeeeeeeeee eeeeeeeeeee-8,8-eeeee (888.8e, 8.88eee) eee MeMMM8M (88.8e, 8.888eee) eee eeeeeeee (8e), eee eee M8M eeee eeeeee eee eeeeeeeee ee e MeeeMeeee eeeeeeeee. Me eeeeeeeeee, eee eeeeeee eee eeeeeee (~8°M), eee eee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eee eeeeee eeee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee eeee M8M (8M), eee eeeeeee eee 8e. Meeeeeeeee eee eeeeee eeeee eeeeeee eeeeeeee eeee 8-[(8-eeeeeeeeeee-8-ee-8-ee)eeeee]eeeeeeeeeeee; eeeee: 888.8e (88%); ee 888888°M.

Mee eeeee eeeeeee (888.8e, 8.888eee), eeeee M8MM8 (888e, 8.888eee), eee MeMe (8.8e, 8.888eee) eeee eeeeeeeee ee MMM (8M) eee eeeeeeee eee 8e, eee eeee eee eee eeeeeee eee eeeeeeee eeee eeeeee (8M) ee eeeeeeeeeee eee eeeeeeeeee, eeeee eee eeeeeeeee, eeeeee eeee M8M, eee eeeee; eeeee: 888.8e (88%); ee 888888°M (eMeMM).

M,M-Meeeeeee-8,8,8,8-eeeeeeeeeeeeeeeee-8-eeeee (8); Meeeeee Meeeeeeee:[‌88‌]

Meeeee 8-eeeeeeeeeeeee (88.8e, 888eeee), eeeeeeeeeeeee (88.8e, 888eeee), MMM (8.8e), eee MMMM (88eM) eeee eeeeee eee 8e ee ee eee eeee ee 888°M. Mee eeeeeee eee eeeeeee ee eeee ee ~888°M eee eeee eeeeee eeee 8M ee MeMM (888eM) eee eee. Meeeeeeeee eeee Me8M (8×888eM) eeee ee eeeeeee eeeee eeee eee eeeeee eeee 8M ee MeMM (88eM), eeeee (M8MM8), eee eeeeeeeeee. Meeeeeeeeeee (888888°M/8.88Meee) ee eee eeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeeeee (eeeeeeeee eeeee) eeee eee eeeeeeeeeeee; eeeee: 8.8e (88%); ee 888888°M.

8-Meeee-8,8-eeeeeeeee-8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeeeeeee (888ee, 8.88eeee) eee eeeee ee e eeee ee 8-eeeee-8-eeeee-8,8-eeeeee­eeeeeeeeeeeeeee (888ee, 8.88eeee) ee MeMM (8.8eM). Mee eeee eee eeeeeeee eee 8e, eeeeee, eee eeeeee eeee e eeeeeee ee 88% ee MM8 (88eM) eee eeeeeee eee (88eM). Mee eeeeeee eee eeeeeee eee 88eee eee eeeeeeeee eeee MMMe8 (8×88eM). Mee eeeeeee eeeeee eeee eeeeeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8) ee eeee eee-eeeee eeeeeeee: eeeee; 888ee (eeeee); ee 888°M.

8-Meeee-8-eeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

8-Meeeee-8-eeeeeeeeeeeeeeeee (88; 8.8e, 8.8eeee), MeMM8 (8eM, 88.8eeee), eee eeeee MeMMe (8.8e, 8.8eeee) eeee eeeeeeee ee 888°M eee 88e, eeeee ee eeeeeee M8M eee eeeeee. Mee eeeeeee eee eeeeeee ee eeee, eee eeeeeee eee eeeeeeeeee eeee MeMM, eee eee eeeee eeeeeee eee eeeeeeeee, eeeeee eeee M8M eee MeMM, eee eeeeeeeeeeeeee (MeMM) ee eeee eeeeee eeeeeee; eeeee: 8.8e (88%); ee 888°M.

References


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