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10.13.1.1.1.2.1.1.2 Variation 2: From α-(o-Aminoaryl) Ketones

DOI: 10.1055/sos-SD-010-00559

Joule, J. A.Science of Synthesis, (200110407.

The most common methods for the synthesis of α-(o-aminoaryl) ketones are: (1) the acylation of enamines or arenes (FriedelCrafts) with (o-nitroaryl)acetyl chlorides and (2) the ortho nitration of α-aryl ketones, followed in each case by nitro group reduction; these types of process are covered in other categories of Science of Synthesis. Given in the rest of this section are the most important routes to α-(o-aminoaryl) ketones, which have been targeted for the eventual construction of indoles. It is relevant to repeat that once produced, and especially under acid catalysis, α-(o-aminoaryl) ketones readily undergo ring closure with loss of water to generate the aromatic pyrrole ring.

Mee eeeee eeeeeeee 888 eeeeeeeee eeee eeeeeeeeeeee ee 8-eeeeee-8-eeeeeeeeeee 888 eee eeeeeeee eeeeeeeee eee eeeeeeee ee eeeeeee eee eeeee eeee eeeeeee ee eeeeeee eeeeeeeee eeeee eeeee eeeeeeeee.[‌888‌] Me eeeeeeeeeee ee ee eeeeee eee eeeee eeeee eeeee (888), eeee eeeeeee 888 eeee 8-eeeeeeeeeee 888 ee eeeeeeeee eeeeeeeee ee eee eeeeeee, eeeeeeee ee eeeee-eeeeeeeee eeeeeeeeeeeeeee-eeeeeeeeeeeeeee ee eeeee eeeee eeeeeeeeee eeeee e eeeeeeeee ee eeeeeeeee eeeeeeee; eee eeeee eeeeeeeee eee ee eeeeeeeee ee eeeeeeee eeee eeeee eeeeeeeeeeeee ee eeeeee ee eeee ee eeeeeeee eeee eeeee eeeeee eeeeeeeee eee eee eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 8-Meeeee-8M-eeeeeee eeee 8-Meeeee-8-eeeeeeeeeee eee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeee ee eeeeeeeeeeee eeee 8-eeeeee-M-(eeeeeeeeeeeeee)eeeeeee (888), eeeee eeeeeeeeeeee ee eeee, eeeee eeeeeeee ee e 8-(e-eeeeeeeee)eeeeeee (888), eeeeeeeee eeee eeeeee 8-eeeeee-8M-eeeeee (888) (Meeeee 88).[‌888‌]

Meeeee 88 8-Meeeee-8M-eeeeee eee Meeeeeeeee ee 8-Meeeee-M-(eeeeeeeeeeeeee)eeeeeee[‌888‌]

Mee eeeee-eeeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeeee ee eeeeee eeee e-eeeee- ee e-eeeeeeeeeee 888 eeee eeeeeeee ee eeeeeee ee e eeeeee eeeeee, eeeeee eeeeeeeeeee eeeeeeee eeeeeeeeeeee, eeeee ee α-(e-eeeeeeeee) eeeeeee 888 eeeee eeeeeee (888) ee eee eeeeee eeeeeee eeeeeeee eeeeee (Meeeee 88).[‌888‌‌888‌] M eeee eeee eeeeeeeeee eeeeeee ee eee ee eeeee eeeeeeeee ee eeeeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeee eee Meeeeeeeeeeee MMM8 Meeeeeeee[‌888‌‌888‌]

Mee eeeeee ee e-eeeeeeeeeee 888 eee ee eeeeeeeee ee eeeeeeee ee 8,8-eeeeeeeeee eeeeeeeee eeeee eeeeee(M) eeeeeeeee eeee eeeeee eeee, eee 888, ee eeeeeee 888 eeee e 8-eeeeeeeeeee ee 8-eeee eeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeee eee Meeeee-Meeeeeeee Meeeeeeeeeee ee Meeeee eeee e-Meeeeeeeeeeeee[‌888‌]

Me eee eeee eeeee eeee M,M-eeeeeeee-8-(e-eeeeeeeee)eeeeeeeeeee (MeeeeeeeeeMeeeee eeeeeee eeeeeeeeeeeee, eee Meeeeee 88.88.8.8.8.8.8.8.8) eee ee eeeeeeee; eeee eeeeeeee ee eeee eeeeeeee ee ee eeeeeee ee eeeee eeeee ee eeeeeeeeee (888 888);[‌888‌] eeeee ee eeeee eeeeeeee eeeeee eeeeeeeeeeee ee ee eeee eeeeee (888 888).[‌888‌] Me eee eeeeee eeeeeeee (Meeeee 88), eeeeeeeee ee eee eeeee eeeee eee eeeeeeeeeee eeeeeeee e 8-eeeeeeeeeee 888. Me eee eeeeee eeeeeeee, eee eee-eeeeee eeeeeee ee eeeeeee eeeeeeeeeeeeee eeee 888, eeeeeeeee ee eeeee eeeee ee 888 eeeeeee ee e 8-eeeeeeeeeee eeeeee (888) ee eeeee ee Meeeee 88.

Meeeee 88 Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeeeeeee eee M-Meeeeeeeeeeeeeeeeeee ee ee M,M-Meeeeee-8-(e-eeeeeeeee)eeeeeeeeee[‌888‌]

Meeeee 88 8-(8-Meeeeeeeeeee)-8M-eeeeee: M 8-Meeeeeeeeee Meeeee eee M-Meeeeeeee ee ee M,M-Meeeeee-8-(e-eeeeeeeee)eeeeeeeeee[‌888‌]

Meeeeee, eeeeeeeeee ee eee eeeeeeee eeeeeeeee eeeee ee 888 ee eeeeeeeeee ee eeeeeeee (888) MeeeeeeeeeMeeeee eeeeeee 888 eeeee eeeeee 888 eeeee ee eeeeeeeee ee eee eeeee eeeee eeeeee ee eeeeeee e 8,8-eeeeeeeeeeeee 888, ee eeeee ee Meeeee 88.[‌888‌]

Meeeee 88 M 8,8-Meeeeeeeeeeee Meeeee eee Meeeeeeeee ee ee α-(e-Meeeeeeee) Meeeee[‌888‌]

Mee eeeeeeeee ee eeeeeee eeeeeeee,[‌888‌] eeeeee eeeeeeeeeeee (Meeeee 88),[‌888‌] ee Meeeeee'e eeee[‌888‌] eeeeee eeee e-eeeeeeeeeeeeeee eeeeeeeee, e.e. 888, eeeee α-(e-eeeeeeeee) eeeeeee eeee ee 888 eeeeeeeee 8,8-eeeeeeeeee eeeeeee Meeeeee eeeeeeee. Meeeeee eeeeeeeee eeeeeeeeee eeeee ee ee eeeeee, eeeeee 8-eeeeeee-8M-eeeeee-8-eeeeeee (888), ee eee eeeee eee.

Meeeee 88 Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeee eee Meeeeeeee ee e 8,8-Meeeeeeeee Meeeeeee eeee ee e-Meeeeeeeeeeeeee Meeeeeee[‌888‌]

Meeeeee eeeeeeeeeee eeeee ee α-(e-eeeeeeeee) eeeeeee eeeeeeee eeeeee eee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeee eeeee ee eeeee ee ee eeeee eeee e eeeeeeeee, e.e. eee eeeee ee eeeee eeeeeeeeeeee[‌888‌] ee ee eeeeeeeeeeeee eeeeee 888 eeee 888 eee eeeeee 8,8-eeeeeeee-8M-eeeeee (888) (Meeeee 88).[‌888‌]

Meeeee 88 8,8-Meeeeeee-8M-eeeeee eee Meeeeeeee Meeeeeeeeeee ee Meeeee ee e 8-Meee-8-eeeeeeeeee[‌888‌]

Meeeeeee eeeee eeeeeeeee eee ee eeee ee eeeeeeee[‌888‌] eeee eeeee eeee eeeeee eeeee eeee(eeeeeeeeeeeee)eeeeee (eeeeeeeeeeeeee)eeeeeeeeee (MMMM); Meeeee 88 eeeee eee eeeeeeee eee-eeeeeeee eeeeeeeeeeee eeeeeeeee 888 eeee eeeeeeeeeee ee 8-eeeeee-8-eeeeeeeeeeee (888) eeee 8-(eeeeeeeeeeeeeee)eeeeeeeeeee (888), eeeee eeeeeeee ee eeeeeee eeeeeeeee, ee eeeeeee e 8-(e-eeeeeeeee)eeeeeeeeeeeee 888 eee eeeeee 8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee (888).[‌888‌]

Meeeee 88 8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee eee e Meeeeeeeee/Meeee Meee Meeee Meeeeeeeeeee[‌888‌]

Me e eeeee eeeeeeeee eeeeeeeeeeee eeeeeeee, eee eeeeeeee ee 8,8-eeeeeeeeee eeeeeee eeee eee ee eeeee-8,8-eeeeeee eeeeeee eeeeeeeeeeee (888) ee eeeeeeeeeeeee, eeeeeeeeee α-(e-eeeeeeeee) eeeeeee, e.e. 888, eeee eeeeeee, eeee 8,8-eeeeeeeeee eeeeeeee, eeee eeeeee 8M-eeeee-8-eeeeee, 8-eeeeee-8M-eeeee-8-eeeee (888) ee eeee eeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 8-Meeeee-8M-eeeee-8-eeeee eeee Meeee-8,8-eeeeeee Meeeeee Mee(eeeeeeeee)[‌888‌]

Mee eeeeeeee ee e-eeeeeeeeeeeeeeeeeee eeeee eeee eeee eeeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee eeeeeeee 8-eeeeeee-8-eeeeee-8-(e-eeeeeeeee)eeeeeee 888 eeee 888 eeeee eee ee eeeeeee ee eeee 8M-eeeeee (8) eeeeee ee eeee eeeeeeee (Meeeee 88).[‌888‌] Me e eeeeeeeeee eee, eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeee eeeeeeee 8-eeeee-8-eeeeee-8-[(e-eeeeeeeee)eeeeeeeee]eeeeeee, eeeee eeee eeeeeee eeeee eeeee eeeee eeeeeeeee.[‌888‌] 8-Meeeeeeeeeeeeeeeeeeee eeeeeeee eeeeee eeee eeee-8,8-eeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee eeeeee 8-eeeeee-8-(8-eeeeeeeeeee)eee-8-eee eeeee, ee eeeeeeeeee eeeeeeee ee eee eeeeee eeee (ee. Meeeeee 88.88.8.8.8.8.8.8.8) eee eeeeeeeee ee eee eeeee eeeee, eeeeeeee 8M-eeeeee eeeeee.[‌888‌] Meeeeeeeeeeee, e-eeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeee eee ee eeeeee eeeeeeee ee eeeeeeeeee ee eeeeeeee.[‌888‌]

Meeeee 88 8M-Meeeee eee Meeeeeee Meeeeeeee ee ee Meee Meeee[‌888‌]

Mee eeeeeeee ee M-eeee-M-eeeeeeeeeeeeeeeeee 888 eeee eeeeeeee 888 eeeeeeee eeeeeee 888 eeeee eeeeeeeee ee eeeeeee ee eeeeeee ee α-(e-eeeeeeeeeeeee) eeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 α-(e-Meeeeeeeeeeee) Meeeeee eeee M-Meeeee-M-eeeeeeeeeeeeeeeeee eee Meeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeee-8-eeeeee-8M-eeeeee (888, M8=8-Me); Meeeeee Meeeeeeee:[‌888‌]

Meeee M8, e eeeeeee ee 8-(8-eeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeeee (8.88e, 88eeee), eeeee eeeeeeee (8.8e, 88eeee) eee eeeee Me8M (88eM) eee eeeee ee eeeee eeeeeeeeeeeee (8.8e, 88eeee) eeeeeeee ee 8°M. Meeee eeeeeeee eee 8e ee ee, eee MMe eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M, eee eeeeeeee eeee eeee eeeeee eeee eeeee eee eeeee (MeMM8) eee eeeeeeeeee ee eeee eeeee 8-(8-eeeee-8-eeeeeeeeeee)-8-eeeeeeeeeee eeeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 88:8); eeeee: 8.88e (88%); ee 888888°M.

Meeee 8-(8-eeeee-8-eeeeeeeeeee)eeeee eeeeeeeee (8.8e, 8eeee) eee Me(MMe)8 (8.888e, 8.8eeee) eeee eeeeee ee eeeeeeeee eeeeeee (88eM) eeeee M8 eee 88e. Mee eeeeeee eee eeeeee eee eeeeeeee eeee eeeeeeee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/eeeeeee 8:8) ee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-Meeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

8.8M MeMe (8.8eee, 8.88eeee) eee eeeee eeeeeeee eeee 8eee ee 8-eeeeee-M-(eeeeeeeeeeeeee)eeeeeee (888; 8.88e, 8.88eeee) ee eeeeeee (8eM) ee 8°M. Mee eeee eeeeee eeee eee eeeeeeee eee 88e, eeeeee ee 88°M, eeeeeee eeee MMM (8eM) eeee eeeeeeeeeeee (8.88e, 8.88eeee) eeeee eee eee eeeeeee eeeeeee ee ee. Meeee eee Me8M eeee eeeee eee eee eeeeeeeee eeeeeeee eeeee eeeee (MeMM8) eee eeeeeeeeee, eee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee 8-(8-eeeeeeeeeee)-8-eeeeeeeeeeeee (888); eeeee: 8.88e (88%); ee 8888°M.

8-(8-Meeeeeeeeee)-8-eeeeeeeeeeeee (888; 88ee, 8.888eeee) eeeeeeeee ee eeeeeeee (8eM) eeee eeee M8M (888 μM) eee eeeeeeee ee eee eeeeeeee ee MeM8 (88ee), eee eeeeeee eee eeee eeeeeee ee ee eee 8e. Meeeeeee eeee Me8M eee eeeeeeeeee eeeeeee Meeeee, eeee eeeeeeeeeee ee eee eeeeeeee eeee e eeee eeeee eee eeeeee eeee M8M eee eeeee (MeMM8) eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee eee eeeeeee; eeeee: 8ee (88%); ee 888888°M.

8-Meeeee-8M-eeeeee-8-eeeeeeeeee Meee; Meeeeee Meeeeeeee:[‌888‌]

Meeeeee eeeee M8, ee MMM8 (88eeee) ee eeeeee MM8 (888eM) eeee eeeee eeeeeeeeeeee, eeeeeee (8.88e, 88eeee), e-MeMM (8.888e, 8eeee), e-MeMM (8.88e, 88eeee) eeee 8-eeeee-8-eeeeeeeeeeeee eeee (8.88e, 88eeee). Mee eeeeeee eee eeeeeeeeee eeee MM eeeee, eeee eeeeeee eeeeeeee ee 888ee eee 88e. MM8MM8 (8.8e, 88eeee) eee Me8M (8eM) eeee eeeee eee eee MM8 eeeeeee ee eeeeeeeee eeeeeeeee. Mee eeeeeee eee eeeeee ee ee eee eeeeee eee ee eeee eee eeeeeee; eeeee: 8.88e (88%).

Meeee 8-Meeeee-8M-eeeeee-8-eeeeeeeeeee (888, M8=Me; M8=MMe); Meeeeee Meeeeeeee:[‌888‌]

MeM (88% ee eee, 8.88e, 8eeee) eee eeeeee eeee eeee eee eee eeeee M8, eeee MMM (8eM) eee eeeee 8-eeeeeeeeeeee (8.888e, 8.8eeee) eeeee eeeeeeee eeee eeeeeeee. Meeee eeeeeeee eeeeeeeee eeeeee, MeM (8.888e, 8.8eeee) eee eeeee eeeeeeeeee eee eeee eeee eeeeee eeee eeeeee, eeee 8-eeeeeeeeeee (888; 8.888e, 8eeee) eee eeeee. Mee eeeeeee eee eeeeee ee 888°M eee 8e, eeeeee, eeeee ee M8M (88eM), eee eeee eeeeeee ee eM 88, eeee Me8M (8×88eM) eeee ee eeeeeee eeeeeee. Mee eeeeeeee eeeeeee eee eeeeee eeee M8M (8×88eM), eeeee (Me8MM8), eee eeeeeeeeee, eeee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/eeeeee) eeeeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8.88M MMMe8 ee eeeeeee (8.8eM, 88.8eeee) eee eeeee ee 8-[8-(8-eeeeeee-8-eeeeeeeeeee)eeeee]eeeeeeeeeee (888; 8.88e, 88eeee) eee Me8M (8eM) ee eeeee eeeeeee (88eM) ee 88°M. Meeee 88eee eee eeeeeee eee eeeeeee ee ee eee eeeee 8e, eeeeeeee ee 88°M eeee Me8M (8.8e, 88eeee) eee MeMM (8eM) eeee eeeee. Meeee 8e ee ee, eee eeeeeee eee eeeeeee eeee eeeeeee (88eM) eee eee eeee eeeeee eeee M8M (8×88eM), eeeee (MeMM8) eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee (eeeeee eee, eeeeee/MeMMe) eeee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeeee (888); eeeee: 8.88e (88%); ee 888888°M.

M eeeeeeeeee ee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeeee (888; 8.88e, 8eeee) eee Me/M (88%, 8.88e) ee MeMM (88eM) eee MeMMe (8eM) eeee MeMM (8.8eM) eee eeeeeeeeeeee ee 8.8 eee ee ee eeeeeeeee. Mee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eeeeee eeeeeee Meeeee eee eeeeeeeeee, eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-(8-Meeeeeeeeeee)-8M-eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee M,M-eeeeeeee-8-(8-eeeeeeeeeee)eeeeeeeeee (888; 88.8e, 8.888eee) eee Me8M (88.8e, 8.888eee) ee eeeeeee (888eM) eee eeeee eeeeeeee ee 8-eeeeeeeeeeeee eeeeeeee (88.8e, 8.888eee). Mee eeeeeee eee eeeeeee ee eeeeee eee 88e, eeeeee, eeee eeeeeeeeee M8M eeeee ee eeeeeeee eee eeeeeeeeeeee eeeee, eee eee eeeeee eeeeeeeee, eeee eee eeeeeee eeeee eeeeeeeeee ee eeee ee eee, eeeee eee eeeeeeeee ee eeeeeee (88eM) eee M8M (88eM) eee eeeeee ee eeeeee eee 88e. Mee eeeeeee eeeeeee eee eeeeeeeeee eee eee eeeeeee eeeeeee eeeeeeeee eeee MM8Me8 eeeee eee eeeee eee eeeeeeeeee ee eeee ee eee, eeeee eeee 8-(eeeeeeeeeeeee)-8-(8-eeeeeeeeeeee)-8-(8-eeeeeeeeeee)eeee-8-ee-8-eee (888) ee eeeeeeeeeeeeeee (eeee MeMM); eeeee: 88e (88%); ee 8888°M.

8-(Meeeeeeeeeeee)-8-(8-eeeeeeeeeeee)-8-(8-eeeeeeeeeee)eeee-8-ee-8-eee (888; 88.8e, 8.88eee) ee MMM (888eM), MeMM (888eM) eee M8M (888eM) eee eeeeeee ee eee eeeeeeeeeee eeeeeeee ee Me8M8M8 (88e). Mee eeeeeee eee eeee eeeeeee eee eeeeee ee 88°M eee 88eee, M8M (888eM) eeeee eee eeeee 88eee ee ee, eeeeeee Me8M8M8 (88e) eee eeeee eee eee eeeeeee eeee ee ee eee 88eee. Meeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeeeee eeeeeeee eee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeee eeeee, eeeee eee eeeeee eeee M8M. Mee eeeeeeee eee eeeeeee eeee 8M MMe (888eM) eee eeeeee ee 88°M eee 88eee, eeeeeeeee ee eeeeeee, eeeeeee eeeee eeeeeeee eee eeeeeeee eee eeeeeeee eee. Meeeeeeeeee ee eee eee eeeeee, eee eeeeeeeeeeeeeeeee (eeeeee) eeee eee eeeeeee; eeeee: 8.8e (88%); ee 8888°M

Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeee eeee (Meee; Meeeeee; Meeeee, Meeeeee Meeeeeeee), Meeeeeeee (8888), e.888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

Me 8-eeeeeee-8-(eeeeeeeeeee)eeeeee eeee (88.8e, 8.8eee) eeeeeeeee ee eeeee eeeeeee (888eM) eee eeeee MMMe8 (88.8e, 8.88eee) eee eeee eee MMM (8eM) eee eee eeeeeee eeee eeeeeeeee eeeeeeeee eee eeee eeeeeeee 888. Meeeee 8-eeeeeeeeeeee (88.8e, 8.88eee) ee eee MMM (888eM) eee eeeee eeeeeeee ee MeM (88.8e, 8.88eee) ee eee MMM (888eM) ee 8°M eeee 88eee. Meee eeeeeee eee eeee eeeee ee eee eeee eeeeeeee 888 eee eee eeeee eeeeeee ee ee eeeeeeeee. M8M (888eM) eee eeeee, eee eeeeeee eeeeeee eee eee eeeeee eeeeeeeee, eeee eee eeeeeee eeeee eeeeee eeee eeeee, eeeee (Me8MM8) eee eeeeeeeeee, eeeeeeeeeee ee eee eeeeeee eeee eeeee, ee MeMM, eee eeeeeee, eeee eeeeee 8-eeeeee-8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeee; eeeee: 88.8e (88%); ee 8888°M.

Meeeee 8-eeeeee-8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeee (88.8e, 8.88eee) ee MeMM (888eM) eee eeeeeee eeee ee MM8 (88eM); eeeee 88eee e eeeeeeeeeee eeeeeeee eee eee eeeeeee eee eeeeeee eee e eeeeeee 88eee eeee eee eeeee eeeeeeee eee. Mee eeeeeeeeeeeeee ee eee eeeeeeee eeeeeee eee eeee eeeee ee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeee (888) eeeee eeee eeeeeeee eee eeee eeeeeee eeeeeeeeeeee; eeeee: 88.8e (88%); ee 8888°M.

Me eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeee (888; 88.8e, 8.88eee) ee eee MeMM (888eM) eee eeeee Me/M (88%, 8.8e) eeee MMM8MM8 (88.8e, 8.8eee) eee eeeee eee eee eeeeeee eeeeeee ee ee eee 8e eeee eeeeeeee eeeeeee Meeeee eee eeeeeeeeee ee eeee eee eeeeeee ee e eeeee eeeee eee eeeeee eeee eeee M8M, eeeeeeee eee eeeee; eeeee: 88.8e (88%); ee 8888°M.

8,8-Meeeeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeeeeeeeeeee (88.8e, 8.8eee) eee eeeeeeee MMM (88e, 8.88eee) eeee eeeeeeeee ee MMMM ee eeeeeeee eee 88eee, eeee e eeee ee 8-eeeeee-8-eeeeeeeeeeee (888; 88.8e, 8.8eee) ee MMMM (8eM) eee eeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeee ee 88°M eee 8e, eeee eeeeee eeee M8M eee 8-(8-eeeeeeeeeee)-8,8-eeeeeeeeeeeeeeee (888) eeeeeeee eee eee eeeeeeeeeeeeee eeee MeMM; eeeee: 88.8e (88%); ee 888888°M.

8-(8-Meeeeeeeeee)-8,8-eeeeeeeeeeeeeeee (888; 8e, 8eeee) ee eeee MeMM (88eM) eee eeeeeee ee eeeeee Me eeeeee (8e, 888eeee) eeeeee eeeeeeeee eee 8e. M8M (888eM) eee eeeee eee eee eeeeeeeee eeeeeeeeeee eeeeeeee eee, eeeee eee eeeeeeee eee eee eeeeeee eeeeeeeee eeee eeeeeeeee eeeeeee, eee eeeeeee eeeeeeeeeeee eeeee eeeeee eeeeeeeee eeeee: eeeee: 8.88e (88%); ee 888888°M.

8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

8-(Meeeeeeeeeeeeee)eeeeeeeeeee (888; 8eM, 8.88eeee) eee 8-eeeeee-8-eeeeeeeeeeee (888; 8.88e, 8eeee) eeee eeeeeeeee ee MMM (88eM) eee eeeeeee eeee MMMM (8.888e, 8eeee) eeeeeeeee ee MMM/MeMM (8:8, 8eM) eeeeeeee eeee 88eee ee 88°M. Mee eeeeeee eee eeee eeeeeeeee ee 88°M eeee Me8 (8.88eM, 8eeee) eeeee eeeeeeee ee eeee eeeeeeeeeee eee eee eeeee eeeeeee ee eeee ee ee. Me8M (8.8e, 88eeee) eee eeeee eee eeeee 8e ee ee, ee eeeeee eeeeeeeee eee eeeee eee eee eeeeeee eeeeeeeee eeee Me8M, eeeeee eee eeeeeeeeeee ee eee eeeeeee eeeeeee eeee 8-(8-eeeeee-8-eeeeeeeeeee)eeeeeeeeeeeee (888) eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8.888e (88%).

8-(8-Meeeee-8-eeeeeeeeeee)eeeeeeeeeeeee (888; 8e, 8.8eeee) eee eeeeeee eeee Me eeeeee (8.88e, 88eeee) eee MeMM (8.88e) eeeeeeee eeee MeMMe (8.88e) ee eeeeeeeee MeMM/M8M (8:8, 88eM) eee 8e. Mee eeeeeee eee eeeeee eee eeeeeeeeee eee MM8Me8 eeee ee eeeeeee eeeeeee eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MMe8/MM8Me8 8:8) ee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888°M.

8-Meeeee-8M-eeeee-8-eeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M,M-(Meeeeeeee-8,8-eeeee-8,8-eeeeeeeee)eee(eeeeeeeee) (888) eeeeeeeee ee eee eeeeeee ee eee eeeeeee eee eeeeeee eeee e eeeee eeeeeeeeee ee eeeeeee-8,8-eeeee eee e eeeee eeeeee ee MeMMe ee eeee 8-[8,8-eee(eeeeeeeeeeee)eeeeee]eeeeeee-8,8-eeeee. Mee eeeeee 888 (8e, 8.8eeee) eee eeeeee ee eeeeeeeee eeeeeeee-eeeeeee MMe (88eM) eee 88e. Meeeeeeeeeee eeeeeee eeee eee eeeeeee eeee eee eeeeee eeeeeee ee eeeeeeeeee eeee eee eeeeeeee eeeee ee eM 8 ee eee eeeeeeee ee 88% ee MeMM eee Me8M eeee ee eeeeeee eeeeeee (8.88e, 88%) eeeee eee eeeeeeee ee eeeeeeeeeee (888°M/88Meee), eeeeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8M-Meeeee (8); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeeeeeee (888; 8.88e, 88eeee) eee eeeeeeeee ee 88M MMe (8.8eee, 88eeee), eeee eee eeee eeeeee ee 8°M eee e eeee eeee ee MeMM8 (8.88e, 88.8eeee) ee M8M (8eM) eeeee eeee 88eee. Meeee e eeeeeee 88eee, eeee (88ee, 8.8eeee) ee M8M (8eM) eee eeeee. Meee eeee eee eeeee eeee 88eee ee e eeee ee eeeee eeeeeee (8.88eM, 88eeee) eee MeMe (8.88e, 88eeee) ee eeeeeee/M8M (88:88, 88eM) ee 8°M. M eeee eeee ee MeMe8 (8.88e, 8.8eeee) ee M8M (8eM) eee eeeee eeee 88eee eeeeeeeee ee eee eeeeeeeee ee M8. Mee eeeeeee eee eeeeeeeeee eeeee 88°M eee 8e eee eeee eeeeeee ee ee eee 8e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eeeee ee M8M eee MM8Me8 (8×88eM) eeee ee eeeeeee eee eeeeeee, eee eeeeeee eeeee eeeeee eeee M8M, eeeee, eee eeee eeeee (MeMM8) eee eeeeeeeeee. Meeeeeeeeeee eeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:88) ee eeee 8-eeeeee-8-(8-eeeeeeeeeee)eeeee eeeeeee (888); eeeee: 8.88e (88%); eee; eee 8-(8-eeeeeeeeeee)eeeeeeeeeeee; eeeee: 8.88e (88%).

8-Meeeee-8-(8-eeeeeeeeeee)eeeee eeeeeee (888; 8.88e, 8eeee) eee Me eeeeee (8.88e, 88.8eeee) eeeeeeee eeee MeMM (8.8e, 88eeee) eee MeMMe (8.88e, 8eeee) eeee eeeeee ee eeeeee ee MeMM/M8M (8:8, 888eM) eee 8e. Mee MeMM eee eeeeeeeeee eeee MM8Me8 (8×88eM) eeeeeeee ee eeeeeee eee eeeeeee eeeeeeee, eee eeeeeeee eeeee eeeeee eeee M8M eeee eeeee, eee eeeee (M8MM8) eee eeeeeeeeee, eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:8) eeeeee 8M-eeeeee; eeeee: 8.88e (88%); ee 8888°M.

References


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