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16.19.1.1.6.4 Method 4: Condensation of Pyrimidin-4-amines with a Three-Carbon Synthon

DOI: 10.1055/sos-SD-016-01443

Sako, M.Science of Synthesis, (2004161180.

The condensation of pyrimidin-4-amines with a three-carbon donor having reactive centers at C1 and C3 is one of the more important methods for the construction of pyridopyrimidines. In most cases, the reagent contains ester, nitrile, activated vinyl, or related functional groups and, where there is a potential leaving group present, such as chloro, alkoxy, or amino, nucleophilic attack is followed by elimination so that the initial result is vinylic substitution of the heterocycle. Normally, attack occurs at C5 of the pyrimidinamine and a bond is established between it and the more reactive site in the reagent.[‌614‌] In some cases, stable intermediates can be isolated. An illustration of this type of synthesis is the palladium-catalyzed carboncarbon coupling of 5-iodopyrimidin-4-amines with ethyl propenoates, or but-2-enoates, to give the corresponding pyridopyrimidinones 92 (Scheme 38).[‌570‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeeee-8-eeeeee eeee Meeee Meeeeeeeeee[‌888‌]

Meeee eeeeeeee eeeeeee eee eeeeeeeeeeee ee 8-(eeeeeeeeeee)-8,8-eeeeeeeeeeeeee eeee eeeeeeeeeeeee eeee ee eee eeeeeeee ee eeeeee eeeeeeeee/eeeeee eeee ee 888°M ee eeee eee eeeeee 88 ee 88% eeeee (Meeeee 88).[‌888‌] Meeeeeeee eeeeeee eee eeeeeeee ee eee eee ee eeeeeeeeeeeee ee eeeee ee eeeeeeeee.[‌888‌] Meeeeeeeee eeeeeeee ee eee ee eeeeeeeee ee eeeeee eeeeeeeee/eeeeee eeee ee eee eeeeeeeeeeeeeeee eeeee ee eeee eeee ee eeeeeeeeeeee;[‌888‌] eee eeeeee eeeeeee eeeeeeeeeee ee eeee eeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeeeeee eeeeee eeeeeeeeeeee eeeeeeee eeeeee ee M8.[‌888‌] Meeeeee eeeeeeeee ee 8-(eeeee ee eeee)eeeeeeeeeeee eeee eeeee eeeeeeeee ee 888888°M eeee eee eeeee ee e eeeeee eee eeeeeeeee eeeee ee 8-eeeeeeeeeeeee[8,8-e]eeeeeeeeeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeeee MeeeeMeeeee eeeeeeee eeeeeee ee eeeeeeeeeeee, e.e. eee eeeeeeee ee eeeeeeeeee eeee (eeeeeeeeeeeeeee)eeeeeeeee ee eeeee 888°M, eee eeee ee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeee Meeeeeeeeeee ee Meeeeeeee-8-eeeeee eeee Meeeeee Meeee[‌888‌]

Mee eeeeeeeee ee 8-eeeeeeeeeeee eeee (eeeeeeeeeeeeeee)eeeeeeeee eeeee eee eeeeee eeeeeeeee ee eeeeee eeeeee[8,8-e]eeeeeeeeee-8,8,8(8M,8M,8M)-eeeeeee ee, ee e eeeeee eeeeee, eeeeee[8,8-e]eeeeeeeeee-8,8,8(8M,8M,8M)-eeeeeee (eee ee-eeeeee eeeeee MeeeeMeeeee eeeeeeee). Meee, eeee 8-eeeee-8,8-eeeeeeeeeeeeee eee eeeeeee (eeeeeeeeeeeeeee)eeeeeeee eee eeeeeeee ee eeeeee eeee, eee eeeee 88 ee eeeeeeee (Meeeee 88).[‌888‌] Meeeeee eeeeeeee ee eeee eeeeee eee eee eeeeeee eeeeeeeeeeeee ee eeeeeee (eeeeeeeeeeeeeee)eeeeeeee eeee eeeeee 8-eeeee-[‌888‌] ee 8-(eeeeeeeeeee)-8,8-eeeeeeeeeeeeee[‌888‌] ee 888888°M, ee eeee 8-eeeee-8-eeeeeeeeeeeeeeee-8(8M)-eee[‌888‌] ee eeeeee eeee, ee eeeee eee eeeeeeeeeeeee 8,8,8-eeeeee-8,8,8,8,8,8-eeeeeeeeeeeeeee[8,8-e]eeeeeeeeee-8-eeeeeeeeeeee. Meeeeeeeeeeeeee eeeeeee eee eeee eeeeee ee eee eeeee-eeeeee eeeeeeee eeeee ee eeee eeeeeeee.[‌888‌,‌888‌,‌888‌,‌888‌] 8,8-Mee(eeeeeeeeeeeeee)eeeeeee (eeeeee eeeeeeeeeee) eeee eeeee, eeeeeee, ee eee eeeeeeeee ee M8 eeeee eeee 8-eeeeeeeeeeee ee eeeeeeeeeeeeeeeee/eeeeeeeee eeeeeeeee ee eeee eeeeee[8,8-e]eeeeeeeeeee.[‌888‌] Meee, eeeeeeeeee ee eee eeeeee eeee ee eee eeeeeee ee eee eeeeeee ee eeeee eeeeee eeeeee eee eeeeee 88 (M8=MM8; M8=MM; M8=MMe) ee 88 (M8=MM; M8=MM8Me; M8=MMe), eeeeeeeeeeee. Meeeeeeeeeeee, eeeeeeeeee ee 8,8-eee(eeeeeeeeeeeeee)-8-eeeeeeeeeeee ee eee eeeee-eeeeee eeeeeeeee eeeeee eee eeeeeeeee ee eee eeeeee 88 (M8=M8=Me; M8=MMe; M8=M; M8=Me8) (Meeeee 88).

Meeeee 88 Meeeeeeeeeee ee Meeeeeeee-8-eeeeee eeee Meeeeeeee Meeeeee[‌888‌,‌888‌]

8,8-Meeeeee-8-eeeeeeeeee-8,8-eeeeee eee eeeeee ee eeeeeeeeeeeee eeeeeeeeeee. Mee eeeeeee, ee e M8 eeeeeee eeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee, eee eeeeee eeeee ee eeee e eeeeeee ee eeeeeeeee eee eee eeeeeeeee eeeeeeeeeeee eeeeeeee ee e eeeeeeeeeeeee[8,8-e]eeeeeeeeee. Meeeeeeeeeeee ee eee eeee eeee eeee eeeeee ee eeee ee eeeeeeeeeeeee ee eeeee eee eeeeeeeeeee eeeeeeeeeeeeeeeeee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeee ee Meeeeeeee-8-eeeeee eeee 8,8-Meeeeee-8-eeeeeeeeee-8,8-eeeeee[‌888‌]

Mee Meeeeee eeeeeeee ee 8-eeeeeeeeeeee ee (eeeeeeeeeeeee)eeeeeeeeeee eeeeee, eeeeee, ee eeeeeeee eeeeeee ee eee eeeeeeeee ee eeeeeee eeee eeee eeeeeee. Mee eeeeeeee eeeeeeee eee eeee ee eeeeeeee, ee eeeeeeee, ee eee (ee eeee eeeeeeeeeee ee e eeeeee eeeeeeee ee eee eeeeeee) eeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee 88.[‌888‌‌888‌] Me ee eeeeeeeeeeee, eeeeeeeeeeeeeeeeeeeeee eeeeeeee eeee 8-eeeee-8-eeeeeeeeeeeeeeee-8(8M)-eee (88) ee eeeeee eee eeeeeeeeeeeeeeeeeeeeeeeeeeee 88 ee eee eeeeeee eeeeee ee 88% eeeee (Meeeee 88).[‌888‌] Me eee eeee ee 8-(eeeeeeeeeeee)eeeeeee, eeeeeeeeeeeee ee eeeeeeeeeeee ee eeeee eeeeeeeeeee.

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee 8-Meeeeeee-8-eeeeeeeeeee[‌888‌‌888‌]

Meeeeee eeeeeeeeeeee ee 8-eeeee-8-eeeeeeeeeeeee eeee eeeee 8-eeeeee-8-eeeeeeeeeeeeeeeee eeeeee eee eeeeeeeeee ee eeeeee 888 (Meeeee 88).[‌888‌] Meeee β-eeeeeeeeeee eeeeeeeee[‌88‌,‌888‌] eee eeeeeee[‌888‌] eee eeee eeeeee eee eeee eeee ee eeeeeeeeeee; eeeeeee, eeeeeee eeeeeeeeeeeeeeee ee eeeeeeee ee eee eeee ee eeee 8-eeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeee 8-Meeeee-8-eeeeeeeeeeeeeeeee[‌888‌]

Meee eeeeee ee eeeeeeeeeeeeeeeeeeeeeeeeeeeee 888 ee eeeeeeee ee e Meeeeeee-eeee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeee eeee 8-eeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌‌888‌,‌888‌‌888‌] M eeeee-eeeee eeeeeee (eeeee Meee ee MMMMMM eeeeee) eeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeee 8-eeeeeeeeee- ee 8-eeeeeeeee-β-eee eeeeee eeee 8-eeeeeeeeeeee ee eeeeeeeeeeeeeeeee. Mee eeeeeee eeeeeee eee eeeeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeee(MM) eeeeeee, eee eee eeeeee[8,8-e]eeeeeeeeeee eee eeeeeee eeeeeee eeee eee eeeee ee eee eeeeee ee eeeeeeeeeeeeeee eeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee 8-Meeeeeeeeeeeeeeee[‌888‌,‌888‌‌888‌]

Meeeeee eeeeeeeeee-8,8-eeeeeeee[‌888‌] ee -8,8,8-eeeeeeeee[‌888‌,‌888‌,‌888‌‌888‌] eeee β-eee eeeeee ee M-eeeeeeeeeeeeeeeee ee eeeeeeee eeeee ee eeee eeeeeeeee; eeee, eee eeeeeeeeeeeeeeeeee 888 ee eeeeee ee 88% eeeee eeee eeeee 8-eeeeee-8-eeeeeeeeeeee ee eeeeee eeee eeeeeeeeee-8,8,8-eeeeeeee (Meeeee 88). Mee eeeee eeee ee eee eeeeeeee ee M-eeeeeeeee ee eee 8-eeeee eeeee ee eee eeeee eeeee.

Meeeee 88 Meeeeeeeeeee ee Meeeeeeeee-8,8,8-eeeeeeee eeee Meeee 8-Meeeee-8-eeeeeeeeeeee[‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeee ee eee eeeee eeeeeeeeeeeeeeee, eeeeeeee eeeeee eeee 8,8-eeeeeeee-8-(eeeeeeeeeee)eeeeee ee 8888°M ee eeeeeeeee ee M8 ee eee eeeeeeeeee eeee, eeeeee, eeeee eeeeeeeeeee, eee eeeeee 888.[‌888‌] Me eee eeee ee eeeeeeeee-eeeeeeeeeee Meeeeee'e eeeee,[‌888‌,‌888‌,‌888‌] eeeeeeeee,[‌888‌] eee eeeee eeeeeeee,[‌888‌,‌888‌] eee eeeeeeeeeeeee 8-eee eeeeeeeeeee 888 eee eeeeeeee eeee 8-eeeeeeeeeeee eee eeeee eeee eeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeeeeee[‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeeee eee eeeee M-eeeeee eeeeeeeeeee eeeee eeee (eeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee ee eeeeeeee ee eeeeee ee eeee eee eeeeeeeeeeeee Meeeeee eeeeeee, eeeee eee ee eeeeeeee ee eeeeeee ee eeeeee eeee ee eeee eee eeeeeeeeeeeee eeeeee[8,8-e]eeeeeeeeeee. Mee eeeeeee, eee eeeeeeeeeeeeeeeeee 888 ee eeeeeeee ee eeeee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee (8-eeeeeeeeeeeeeeee) ee eee eeeeeeee eeeeeeee (Meeeee 88).[‌888‌] Meeeeeeee ee 8-eeeeee-8M-eeeeeeeeeeeeee eeee 8-eeeeeeeeeeee ee eeeeee eeee eeeeee eeeeeeee eeee eeeeeee eeeeeee eeeeeee eeeeeeeeeeee. Meee ee eeeeeeee ee eeeeeeeeeeee eeeeeee eee eeeeee eee eee 8-eeeee eeeeee ee eeee 8-(8-eeeeeeeeeeee)eeeeeeeeeeeeeeeeeeeeee 888 (M=M). Me eee eeeee eeee, eee eeeeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeee eeeeee eeeeeeeeeeee ee eee eeeee eeeee eeee eee eeeee eeeeeeee eeeee, eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee eeeee eeee eee eeeeeeee eeeeeee eeeee ee eeeeeee e eeeeeeeeee 888 (M=M) (Meeeee 88). 8-Meeee-8-eeeeee-8,8-eeeeeeeeeeeeeeee-8(8M)-eeee eee ee eeee eeeeeee ee 8-eeeeeeeeeeee ee eeeee eeeeeeeee eeeeeeeee eee eeee eeeeeeeee 888 (M=M) eee 888 (M=M) ee eeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eee Meeeeee Meeeeeeee eeee Meeeee[‌888‌,‌888‌]

8,8-Meeeeeeeeeeeeee, eeeeeeeeee eeee eeeeeeee-eeeeeeeeeee eeeeee ee M8, eeeee ee Meeeeee eeeeeeeee eee eeeeeee eeee-eeeeeeeee eeeeeeeee ee 8-eeeeeeeeeeee. Mee eeeeeee eeee eeeeeee eeee eee eeeeeeeeeee ee M,M-eeeeeeeeeeee. Mee eeeeeee, eee eeeeeee 888 eeeeeeee eeee eee 8-eeeeeeeeeeeeeeeeeeee 888 ee eeee eee eeeeee 888 (eeeeeeee eee eee eeeeeeeeeeeee 888 eee 888), eee eee eeeee ee eeee 88% (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8,8-Meeeeeeeeeeeeee eee 8-Meeeeeeeeeee[‌888‌,‌888‌]

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

Meeeee 88 Meeeeeeeeeee ee Meeeeeeee-8-eeeeee eeee Meeeeeeeeeeeee eee Meeeeee Meeeeeeee[‌88‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeee ee eee eeeee eeeeeee,[‌888‌] eee eeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee eeee 8,8,8,8-eeeeeeeeeeeeeeeeee eeeee eeeee ee ee eeeeeeeeee eeeeeeeeeeee 888, eeeee ee eeeeeeeee eeeeeeeee ee eeeeee eeee ee ee eeeeeeeeeeee eeeeeeee eeee ee 888°M eeeeeeee 8-eeeeeeeeeee[8,8-e]eeeeeeeee-8(8M)-eee (888) (Meeeee 88).[‌888‌] Meeee eeeeeeee eee eeee eeee ee eeeeeeeeee eee 8,8-eeeeeeeeeeeeeeee, eeeee eeeeee eeeeeeeeee eeeeeeeee[‌888‌] ee eee eeee[(eeeeeeeeeeeeeee)eeeeee]eeeeeee eeeeeeeee ee eee eeeeeeeeee eeeee.[‌888‌‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeee-8(8M-)-eee eeee 8,8,8,8-Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeee eeeeeeeeeeee eee eeeeeeee ee eee eeeeeeeee ee 8-eeeee-8-(eeeeeeeeeee)eeeeeeeee-8(8M)-eee eeee eeeeeeeeeeeeeeee,[‌888‌] eee ee 8-(eeeeeeeeeee)eeeeee eeee 8-eeeeee-8-eeeeeeeeee.[‌888‌] Meeeeee eeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeeeeee ee 8-(M-eeeeeeeeeeee)eeeeee eee 8,8-eeeeeeeeeeeeee-8-eee ee eeeeee eee eeeeeeeeeeeeeeeeee (888, M8=M-eeeeeee) (Meeeee 88).[‌888‌] Meeeee ee eeeee eeeeeeeee eeee eeeeee eeee 88 ee 88%. Me β-eee eeeeeeeee, eeeeee eeee eeeee eeeeeee, eee eeeeeeee ee eeeeeeeee ee M-eeeeeeeee eeeeeeeee-8-eeeeee, eee eeeeeeeee eeeeeee eee eeeeeee eeeeee ee M8 ee eee eeeeeeeeee eeee ee eee eeeeeeee eeeeee eeee ee eee eeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee β-Mee Meeeeee[‌888‌]

Mee eeeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeeeeeeeee ee M8 ee 8-eeeee-8,8-eeeeeeeeeeeeee ee eeeeee eeeeee eeee ee eeeeee, eee eeeeeeeeee eeeeeeeeeee eeeeeee eee eeeee eee 8-eeeee eeeeee, ee eeeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeee, eeeeeee ee eee eeeee 888 (Meeeee 88).[‌888‌] Meeee eeeeeee eeeee-eeeeee eeeeeeeeee ee eeeeeeeee ee eeee eeee eee eeeeeeeeee eeeeee. Meee, eeeee eeeeeee eeeeeeeeee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeee eeeeeee eee eeeee 888,[‌888‌] eee 8-(eeeeeeeeeee)eee-8-ee-8-eeee, M-eeeeeeeeeeeee 8-(eeeeeeeeeeeeee)eeeeeeeeeeeeee,[‌8‌] eee 8-eeeeee-8-eeeeeeeeeeeeee-8-ee-8-eee eeee eeee ee eee eeeeeeeeeeeee eeeeee 888[‌888‌] (Meeeee 88). Me eee eeeeeeeee ee eee eeeeeeeeee eeeeee, eee eeeee eeeee ee eee eeeeee eeeeee eeee eee β-eeeee eeeeee ee eee eeeeeee, eee eeee ee eeeeeeee ee eeeeeeeeeee eeeeeee eeeeeeeeeeeee eeeeee ee eee eeeeeeee eeeee ee eee eeeee eeeeeeeeeee eeee eeeee.[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeeeeee[‌8‌,‌888‌‌888‌]

Mee eeeeeeeeeeeee ee M-(8-eeeeeeeeeeeee)-8-eeeeeeeeeeeeeeeeeeeeeeee, 8-eeeee-8-eeeeeeeeeeeeee,[‌888‌] eee 8-[(eeeeeeeeeeeee)eeeeeeeee]-8,8-eeeeeeeeeeeee-8-eee[‌8‌] eeee 8-eeeeeeeeeeee eeee eee eeeeeeee eeeeeeeeeeeeeeee[‌888‌,‌888‌] ee eeee eeeee ee Meeeee 88. Meeee eeeeeeee eeeeeeeee eeeeeee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee eee 8-eeeee-8-eeeeeeeeeeeeeeeee-8(8M)-eee.[‌8‌] Mee eee eeeeeeeeeee ee eee eeeeee 888, e MeeeeeeMeeeee eeeeee eee ee eeeeeeee. Mee eeeeeeee ee eeeeeeeee ee M8 ee eee 8-eeeeeeeeeeeeeeeeeeee eeeeeeeee eee β-eeeeee ee eee eeeee, eeeee ee eeee eeeeeee eeee eee 8-eeeee eeeee (Meeeee 88).[‌888‌] Meeeeeeeee-8,8,8-eeeeeeee[‌888‌,‌888‌] eee eeeeeeeeeeee eee eeee eeee ee eeeeeeee eee eeee-eeeeeeeee eeeeeeeee eeee α,β-eeeeeeeeeee eeeeeee,[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌] eee eeeeee eee eeeeeeeee eeeeee eeeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeee.[‌888‌] Mee eeeeeee, Meeeeee eeeeeeeee ee 8,8-eeeeeeee-8-eeeeeeeeee-8-ee-8-eee[‌888‌] ee 8,8-eeeeeeeeeeeeeeeee[‌888‌] ee 8-eeeee-8,8-eeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeee, eeeeeeee ee eeee eeeeeee, eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee ee eeeee eeeeeee eeeeeeeeeee. Meeeeee ee α,β-eeeeeeeeeee eeeeeee, Meeeeee eeeeeeee, eeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeeeeee, eee eeeeeeee ee eee eeeee-eeeeee eeeeeeee.[‌888‌] Me eeeeee 8-eeeeeeeeeeeeeeeeee, eee eeeee eeeeee eee ee eeeeeeee ee eeeeeeeeeeee ee eeeeee ee eee eeeeeee eeeeee eeeee; eeeee, 8-eeeee-8,8-eeeeeeeeeeeeee eeeee eee eeeeeeeee eeeeeeee eeeeeeeee ee eee eeeeeeeeee eeeeeeee.[‌8‌] Me eeeeeeee ee eeeeee eeeeeee eeeeeeeeeeee eeeeee eeeeee ee e 8,8-eeeeeee ee eee eeeeeeee eeeee, eee eeeeeeeeee eeeeeeeeeeeeeeee eee eee eeeeeeeee eeee eeeee eee eeeeee eeeee 888 (M8=MM8Me; M8=e-Me) (Meeeee 88). Me eee eeeee eeee, ee eeeeeee ee eeeeee ee eeeeee eeeeeeeeee ee eeeeee, eeeeeee eeeeeee eeeeee ee e 8,8-eeeeeee ee eee eeeee eeeee. Me e eeeeeee eeeeeee, eee eeeeeeeee ee eeeeeeeeeeeeee eeee 8-eeeeeeeeeeeeeee-8,8(8M,8M)-eeeeee ee eeeeeeee/eeeee, eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee eeeeeeeee, eeeeee eee eeeeeeeeeeeee 8-eeeee-8,8-eeeeeeeeeeeee[8,8-e]eeeeeeeeee-8,8(8M,8M)-eeeeee.[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeeee[‌8‌,‌888‌,‌888‌]

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

Meeeee 88 Meeeeeeeeeee ee Meeeeeeeeeeeeee eeee Meeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

8-Meeeeeeeeeeeeeeeeee eeeee, eeeeeeee eeee eee eeeeeeeeeee 8-eeeeeeeeeeeeee eeee eeeeeeee,[‌888‌] eeee eeee eeee ee eeeeeeeeee eee eeeeeeeeeeeee eeeeee[8,8-e]eeeeeeeeeee 888 ee eeeeeeeeeeeee eeee eeeeeeeeee-8,8,8-eeeeeeee (Meeeee 88).[‌888‌] Meee 8-eeeee-8,8-eeeeeeeeeeeeee, eeee eeeeeeee eeeeeeeeeeee ee eeeeeeeeee eee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeee ee Meeeeeeeee-8,8,8-eeeeeeee eeee Meeeeeeeeeeee Meeee[‌888‌]

Meeeeeeee ee eee eeeeeeeeee, eeeeeee eeee eeeeeeee-eeeeeeeeeee eeeeee eeeee ee Meeeeee eeeeeeeee eee eee eeeeee ee eee M8-eeeeeeee ee ee eee 8-eeeee eeeee ee 8-eeeeeeeeeeee. Me eeee eeeee, eee eeeeeee eeee 8-(eeeeeeeeeee)eeeeee, eeeeeeee ee 8-eee- eee 8-eeeeeeeeeeeeeeeeeee eeeeeeeeeee, eeeeeeee eeee eeeee eeeeeee Meeeeee eeeeeee, eee eeeeeeee. Me eee eeeee eeee, ee eee eeee ee 8-eeeeeee-8,8-eeeeeeeeeeeeee, eeee eee eee eeeeeeee eeeee eeeeeeee eeeeee[8,8-e]eeeeeeeeeee eee eeeeee.[‌888‌] Mee eeeeeeeee eeeeee ee ee eeeeeeeeee eeeeeeeee ee eeeeee eee eeeeeeee ee eeeeeee ee e M8 eeeeeeeeeee, ee eee eeeeeeeeeeee ee eeeeeee eeee eee eeeeeee.[‌888‌] Mee eeeeeeee ee eeeeee eeeeeeeeee eeee 8-eeeee-8,8-eeeeeeeeeeeeee ee eeeee ee eeeeee eeeeeee eee eeeeee 888 (M8=Me; M8=M) (Meeeee 88).[‌888‌] Me eeeeee eeeee, eeee ee eeeee ee eeeeeeee, eee eeeeeeee eeee 8-eeeeeeeeeeee eeeeee eeeeee 8,8,8-eeeeee-8,8,8,8,8,8-eeeeeeeeeeeeeee[8,8-e]eeeeeeeeee-8-eeeeeeeeeeee.[‌88‌,‌888‌,‌888‌,‌888‌,‌888‌] Me eee eeeeeeeeeeee eeeeee, eee ee eee M eeeeeeeeeeeee, eeeeee ee eeeeeeee, ee ee eee eeeeeeeee ee 8,8-eeeeeeee-8-(eeeeeeeeeee)eeeeee eeee eeeeeeeeeee, eee eeeeeee eeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeeee ee eee eeeeee, eeeeeeee eee eeeee ee eee.[‌888‌] Meeeeeeee, eeeeeeee ee 8-eeeeeeeeee-8-ee-8-eee eeeee eeee 8-eeeeeeeeeee ee eeeeeee eeeeee ee 8°M ee eeee eee eeeee 888 (M8=M) ee eee eeeeee eeeeeeeeee 888 (M8=Me), eeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌,‌888‌] 8-Meeeeeeeeee eee eee 8-eeeeee eeeeeeeeee eeee eeeee eeee eeeeeeee eeeeee-8,8-eeeeeeeeeeeee ee eeeee ee eeeeee ee e Meeeeee eeeeeeee ee M8 ee eee eeeeeeeeeeeeeeee ee eee eeeeeee eeeeee eeeeee eeee. Meee eeeeeee eeee eeeee eee eeeeeeeeeee eeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeeeee ee Meeeeee[‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8,8-Meeeeeeeeeeeeee[8,8-e]eeeeeeeee-8(8M)-eee (88, M8=M8=Me; M8=M); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8,8-eeeeeeee-8-eeeeeeeeeeeee-8-eeeee (8.88e, 8eeee) eee eeeee 8-eeeeeeeeeeeeeeee (8.88e, 8eeee) ee MeMM (8eM) eeeeeeeeee MeMe8 (88ee, 8.88eeee) eee Me8M (8.8e, 8eeee) eee eeeeee ee 888°M ee e eeeeee eeee eee 88e. Meeee eeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeee eeee M8M, eeee eeeeeeee eeee M8MM8, eee eeeeeeeee eeee MMMe8. Mee eeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/MeMMe 8:8]. Mee eeee eeeeeee eee eeeeeeeeeeee (eeeeeee) ee eeeeee eee eeeee eeeeeeee ee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-Meeee-8-{8-[8-(eeeeeeeeeeeeeee)eeeeee]eeeee}eeeeee[8,8-e]eeeeeeeee-8(8M)-eee [88, M8=(MM8)8M8M8-8-MM8Me]; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeeee 8-[8,8-eeeeeee-8-(eeeeeeeeeeeeeeeee)eeee-8-eeee]eeeeeeee (8.8e, 8.8eeee) eee 8,8-eeeeeeeeeeeeeeee-8(8M)-eee eeeeeeeeeee (8.88e, 8.8eeee) ee 88% ee MeMM (88eM) eee eeeeeeee eee 8e. Me eeeeeee, eee eeeeeeeeeee eeee eee eeeeee eee eeeeeeeee, eeeeee eeeeeeeeeeee eeee M8M eee Me8M, eee eeee eeeee. Meee eeee eee eeeee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.8e (88%); ee >888°M.

8-Meeee-8-eeeeeee-8-eee-8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeee[8,8-e]eeeeeeeeee-8-eeeeeeeeeeee (88):[‌888‌]

M eeee ee 8-eeeee-8-eeeeeeeeeeeeeeee-8(8M)-eee (88; 888ee, 8.8eeee) eee eeeeeeeeeeeeeeeeeeeeeeee (888ee, 8.8eeee) ee MeMM (88eM) eeeeeeeeee Me8M (8eM) eee eeeeeee ee eeeeee eee 8.8e. Me eeeeeee, e eeeee eeeeee eeeee eee eeeeeeeee, eeeeee eeee eeee MeMM, eee eeeeeeeeeeee (MeMM) ee eeeeee eee eeeee eeeeeeee; eeeee: 888ee (88%); ee 888°M.

8,8-Meeeeee-8-eeeeee-8-eeeeeeeeeeee[8,8-e]eeeeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeee 8-eeeeee-8-eeeeeeeeeeee (888e, 8.88eee) eee eeeeeeeeee-8,8,8-eeeeeeee (88e, 8.88eee) ee Me8M (888eM) eee eeeeee eeee eeeeeeee ee 888888°M eeeee eee-eeeeeee eeeeeeeee (MeMM eee M8M) eee eeee eeeeeee. Meeee eeeeeee, eee eeeeeeee ee ee eeeee eeeeee ee MeMM eeeeee e eeeeeeeeeee ee eeee; eeee eee eeeeeeeee eee eeeeee eeee MeMM. Mee eeeee eee eeeeeeeee ee eeeeeee M8M (8.8M), eeeeeeeee ee eeeeeeeeee, eee eeeeee eeeee eeee MeMM ee eeeeee eee eeeee eeeeeeee; eeeee: 88e (88%).

8-Meee-8,8-eeeeeeeeeeeee[8,8-e]eeeeeeeeee-8,8,8(8M,8M,8M)-eeeeeee 888 (M=M); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeeeeee 8-eeeeeeeeeeeeeee-8,8(8M,8M)-eeeee (8.8eee) eee 8-eeeeeeeee-8,8-eeeeeeee-8,8-eeeeeee-8,8-eeeee (8.8eee) ee eeeeeee MeMM (888eM) eee eeeeeeee eee 88 ee 88e. Mee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee ee. 88eM eee eeee eeeeee eeee eee eeeee. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeeee eee eeeeee eeee M8M eeeee eee eeeeeeee eeee eeeeeee. Meeeeee eeeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeeeeee (MeMM).

8-Meeeeee-8M-[8]eeeeeeeeeee[8,8:8,8]eeeeee[8,8-e]eeeeeeeeee-8,88(8M,88M)-eeeee 888 (M=M); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeeeeee ee e 8-eeeeee-8M-eeeeeeeeeeeee (8eeee) eee e 8-eeeeeeeeeee (8eeee) ee MMM (8eM) eee eeeeee ee 88°M eee 8e. Mee eeeeeee eee eeeeee eeee eee. Mee eeeeeeeee eeeee eee eeeeeeeee eee eeeeeeeeeeee (MeMM). Mee eeeee eeeeeeeee eeee eeeeeeeee eeeeeee; ee >888°M.

8-Meeee-8-eeeeeeeeeee[8,8-e]eeeeeeeee-8-ee (888, M8=MM8; M8=MM; M8=M8=M; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeeeeeeeeeeee (88.8e, 8.88eee) eee eeeee ee e eeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee-8-ee eeeeeeeeeee (88.8e, 8.88eee) ee eeeee MMe (88eM) eee MeMM (8.8eM), eee eee eeeeeee eee eeeeeeee eee 88e. Me eeeeeee e eeeee eeeeeeeee, eeeee eee eeeeeeeee, eeeeee eeeeeeeeeeee eeee MeMM eee Me8M, eee eeee eeeee ee eeeeee eee eeeee eeeeeeee ee e eeeee eeee eeeee; eeeee: 88.8e (88%). Me eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeee; ee 888888°M.

8-Meeeeeeeeeee[8,8-e]eeeeeeeeee-8,8(8M,8M)-eeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeeee (8.8e, 88eeee) eee 8-(eeeeeeeeeee)eee-8-ee-8-eee (8.8e, 8eeee) ee MeMM (888eM) eee M8M (888eM) eee eeeeeeee eee 88eee. Me eeeeeee eee eeeee eeee eeeeee eee eeeeeeeee eee eeeeeeeeeeee (MMM/M8M) ee eeee eee eeeee eeeeeeee; eeeee: 8.8e (88%); ee 888888°M.

8-Meeee-8,8,8-eeeeeeeeeeeeeee[8,8-e]eeeeeeeee-8(8M)-eee Meeeeeeeeeeee (888, M8=M; M8=M8=Me):[‌888‌]

M eeeeeee ee 8-eeeee-8-(eeeeeeeeeee)eeeeeeeee-8(8M)-eee (8.88e, 8.8eeee) eee eeeeeee eeeeeeee 8-eeeeeeeee-8-ee-8-eee (8.8e, 88.8eeee) eee eeeeeee ee 88°M eee 8e. Meee 8.8M MMe (8eM) eee eeeee ee eee eeeeeee eee eeeeeeee eee eeeeeeeee eee e eeeeeee 88e. Mee eeeeeee eee eeeeeeeeee ee eeeeeee, eee eee eeeeeee eee eeeeeeeeeeee (MeMM) ee eeee eee eeeee eeeeeeee ee eeeeeeeee eeeeeee; eeeee: 8.88e (88%); ee >888°M.

8-Meeeeeeeeeeeee[8,8-e]eeeeeeeeee-8,8-eeeeeee (888, M8=eMe); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee MMMe8 (88.8e, 8.88eee) ee 8,8-eeeeeeeeeeeeee (888eM) eee eeeee eeeeee eeee eeeeeeee eee eeeeeee ee e eeee ee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (88e, 8.888eee) ee 8,8-eeeeeeeeeeeeee (88eM); eeeeeeee eee eeeeeeeee eeeee eee eeeeeeeee ee MM8 eee eeeeeeee. Meeee eeeeeee ee eee eeeeeee, eee eeeeeee eee eeeee ee e eeee ee eeeeeeeeee-8,8,8-eeeeeeee (88.8e, 8.88eee) ee eeeee MeMM (888eM) eee eee eeeeeee eee eeeeeeee ee e eeeee eeee eee 88e, eeee eeee eeeeeeee eeeee eeee MeMM, eee eeeeee eee e eeeeeee 8e. Me eeeeeee, eee eeeeeeeeeee eeee eeeeee eee eeeeeeeee eee eeeeeeeeeeee (88% ee MeMM). Meee eeeeeee eee ee eeeeeee eeee MMe ee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee eeee; eeeee: 88.8e (88%).

References


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