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Please login to access the full content or check if you have access via9.13.1.5.3.1 Method 1: Reaction of α-Aminoacyl or α-Iminoacyl Compounds with 1,3-Diketones or Equivalents
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Black, D. StC., Science of Synthesis, (2001) 9, 481.
The major synthetic route in this category is quite general in its methodology, in which an ester or a ketone bearing an adjacent amino or masked amino function undergoes addition to a 1,3-diketone or one of its many equivalents. Aminomalonate systems, which are most effectively generated in situ from hydroxyiminomalonic esters by reduction with zinc and acetic acid or catalytic hydrogenation, undergo reaction with 1,3-diketones to give pyrrole-2-carboxylic esters. Indeed, similar products are obtained from reactions in which α-hydroxyimino-β-oxo esters are used, with loss of an acyl group being preferred to loss of an alkoxycarbonyl group in the aromatization step.[178–184] Some examples illustrate these features (Scheme 37). Pentane-2,4-dione (256) combines with the hydroxyiminomalonate 257 in the presence of zinc in acetic acid to give the pyrrole-2-carboxylic ester 258.[178] The regioselectivity of this reaction is shown in the similar combination of the unsymmetrical diketone 259 with hydroxyiminomalonate 257 to give the pyrrole 260, as the result of amino reaction with the cyclic carbonyl component.[184] The α-hydroxyimino-β-oxo ester 182 reacts with the diketone 261 to give the pyrrole ester 262, resulting from deacylation.[179]
Meeeeeee eeeeeeeeeeee eeeeee eee ee eeee eeeeeeee, ee eeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeeeeeeee 888 eeee eeeeeee 8-eeeeeeeeeeeee (888) eee eee eeeee eeeee 888.[888]
α-Meeee eeeeee eee α-eeeee eeeeeee eee eeee ee eeee eeeeeeeeeee ee eeeeeeeee eeee β-eeeeeeeeee eeeeeee eee eeee eeeeeee eeeeeee eeeeeee eee eeeeeee ee eeee eeeeee.[888–888] Me eeee eeeeeee, eee eeeeeeeeeeee eeeeeeeee eee ee eeeeeeee,[888] eee ee eeee eeeee eee eeeeeeeee eeeeeeee eeeeeeeee ee Meeeeee 8.88.8.8.8 ee eeee eeeeeeeeee. Me eeeeeee ee e eeeeee eeeeeeeeee ee eeee ee eee eeeeee-eeeeeeeeeee 8,8-eeeeeeeeeeeeeeeee-8(8M)-eee 888 eeee eee eeeeeee 888 ee eeeeeeee eeee eeeeeee eeeee eeeee (888).[888] Mee eeeeeeeeeeeeee ee eeeee eeeeeeeeeee ee eeee eeeeeee.
Meeeee 88 Meeeeeeee ee Meeeeeee eeee α-Meeeeeeee Meeeeeeee eee 8,8-Meeeeeeee[888,888,888,888,888]
Meeeeee 8,8-eeeeeeeeee eeeeeeeeeee eeee eeee eeee ee eeee eeeeeeeee eeeeeeee, eee ee eeeeeeeeee eeeee eeeeeeeee eeee α-eeeee eeeeee eee eeeeeeee. Meeee eeeeeeeeeee eeeeeee eeeeeeeeee eeee eeeeeeeee,[888–888] eeeeeeeeee eeeeee,[888–888] eeeeeeeeee eeeeeeee,[888,888] eee, eeee eeeeeee, eeeeeeeeee eeeeeee eeeeeeeee ee eeeeee-eeeeeeeeeee eeeeee (Meeeee 88).[888,888] Meeeeeee ee 8-eeeeeeeeeeeeeee-8-eee-8-eeeeeeeeeeee (888), eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeeee eeeeeeee eee eeeeeeeeeeeeeeeee, eeee eee M-eeeeeeeeeeeee eeeee 888 eeeee eee eeeeeee eeeee 888 ee eeeeeeee eeeee.[888] M eeeeeee eeeeeeee eeeeee eeeeeee 8-(eeeeeeeeeeeee)eeeeeeee (888) eee 8-(eeeeeeeeeee)-8-eeeeeeeeeeeeee (888) ee eeee eee 8-eeeeeeeeeeeeee 888.[888] Meee eeeeeee eeeeeeee eeee eeee eeeeeeee eeee eeeeeee eeeeeeeeeee. Mee eeeeeeeeeeeeeeee eeeeeee eeeee 888 eee ee eeeeeeee eeee eee 8-eeeeeeeeee-8-eeeee 888 eee eeeeeee eeeee eeeee (888) eeeee eeeee eeeeeeeeee.[888] Mee eeeeeeeeeeeee 8-eeeeeeeeeeeee eeeeeee eeeee, eeeee eee eeeeeeee ee eee eeee eeee eeee eeeeee eeeeeee, eeeeeeeeee eeeeeeee, eee eeeeeeeeeeeeeeeee, eee eeeeeeeee ee eeeee eeeeeeee, ee eeee eeee eeeeee eeeeeeeeeeeeeeee. Mee eeeeeee, eee eeeeeeee ee ee eeeee eeee ee eee M-eeeeeeeeeeeee eeeee 888 eeeee eeeee ee eee M8 eeeeeeee ee e 8-eeee-8-eeeeeeeeeeeeeeeeeee eeeeee eeee ee eee eeee 888 ee eeee eee 8-eeeeeeeeeee-8-eeeeeeeeee eeeee 888.[888] Me eee eeeee eeee, eee eeeeeeeeeeee ee ee eeeee eeeeeeeeeee ee M8 ee eee eeeeeeeeeeeeeeeeeee eeeeee eeeeeeee eeeeee eeeeeeeee eee eeeeee ee eee eeeee ee M8, eeee eeeeeeeeeee ee ee eee eeee-eeeeeeee M8, eee eeeeeee ee e 8-eeeeeeeeeee-8-eeeeeeeeee eeeee. Meee ee eeeeeeeeeee ee eee eeeeeeeeee ee eee eeee 888 eeee eee eeeeeee 888 ee eeeeeeee eeee eee M-eeeeeeeeeeeee eeeee 888.[888]
Meeeee 88 Meeeeeeee ee Meeeeeee eeee α-Meeeeeeeeeeee Meeeeeeee eee Meeeeeeeeee ee 8,8-Meeeeeeee[888,888,888,888,888]
Meeeeee eeeeeeeee ee eeee eeeeeeeeeee eee ee eeeeeee ee eeeeeeeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eeeee eeee e β-eeeeeee eeeee. Mee eeeeeeee eeeeeeee eee eeeeeeeeeeeee ee e eeeeeeee eeeeeee eeeee eeeeeeeee ee eee eeeeee ee eeee eee eeeeeeeeeeeeee, eeeee eeeeeee eeee eee eeeee eeeeeeee eee eeeeeeeeeee, eee ee eeeeeeeee eeee eee eeeeeee. Mee eeee eeeeeeeee eeeeeeeee eeeee eee ee M-eeeeeeeeeeee eeeeee (Meeeee 88).[888,888] Mee eeeeeee, eeeee eeeee eeeeee (888) eeeeeeeee eeeeeeee eeee eee M-eeeeeeeeeeee eeeeee eeeee (888) ee eeee eee eeeee 888, eeeeeeee ee eee eeeeeeeeeee eeeeeee, eee 8,8-eeeeeee-8M-eeeeeee 888, eeeee eeeee eeeee eeeeeeeeee eeeee eeeeeeeeeeeeeee eeee ee eeee eee eeeeeee 888.[888] Meeeeee eeeeeeee eeeee eee ee eeeeeeeeeeeeeeeeee, eeee eee eeeeeeeeee eeee ee eeeeeeee eeeeeee ee eee eeeeeeeeeeeee eeee. Mee eeeeeee, eeeeeeeeeeeeee (888) eee eeeeeee(eeeeee)eeeeeeeeeeee (888) eeee eee eeeeeeeeeee 888, eeeee ee eeeeeee eeeee eeeeeee eee eeeeeeee eeeeeee ee eeee eee eeeeeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeeee ee Meeeeeee eeee α-Meeeeeeeeeeee Meeeeeeee (ee Meeeeeeeeee) eee α,β-Meeeeeeeeee Meeeeeee Meeeeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
Meeee 8,8-Meeeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
M eeee ee eeeeee-8,8-eeeee (888; 8.88 e, 88 eeee) ee MeMM (88 eM) eee eeeeeee ee 88°M eeee eeeee MeMMe (88 e, 888 eeee) eee Me eeee (88 e, 888 eeee). M eeee ee eeeeeee 8-(eeeeeeeeeeee)eeeeeeee (888; 8.88 e, 88 eeee) ee MeMM (88 eM) eee M8M (8 eM) eee eeeee eeeeee 88–88 eee ee 88–888°M. Meeee eeeeeeee ee eeee eeeeeeeeeee eee 88 eee, eee eeeeeee eee eeeeee eeee eee eeeee (888 eM) eee eeeeee. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeeee, eeeeee eeee M8M, eee eeeeeeeee ee 88% MeMM (88 eM). Mee eeeeeeeee Me eeee eee eeeeeeee eee eee eeeeeeee eeeeeeeeeeee ee 88 eM eee eeeee ee eee eeeee (88 eM) ee eeeeee eee eeeeeee 888; eeeee: 8.88 e (88%); ee 888–888.8°M (MeMM).
Meeee 8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeee-8-eeeeeeeeeee (888):[888]
Meeeeee 8-(eeeeeeeeeeee)eeeeeeee (888; 88.8 e, 88.8 eeee) eee Me eeee (88 e, 888 eeee) eeee eeeee eeee eeeeeeee ee e eeee ee 8-eeeeeeeeeeeeeeeeeee (888; 8.88 e, 88.8 eeee) ee MeMM (88 eM) eeeeee 88 eee. Meeee eee eeeeeeeee ee eeeeeeeeeeeeeee ee Me(MMe)8, M8M (88 eM) eee eeeee eee eeeeeeee eee eeeeeeeee eee e eeeeeee 88 eee. Mee eeeeeee eee eeeeeeee eeee eee Me eee eeeeeee eeee M8M (888 eM) ee eeee e eeeeeeeeeee ee eee eeeeeee 888 eeeee eee eeeeeeeee eee eeeee; eeeee: 8.88 e (88%); ee 888.8–888°M (ee MeMM).
Meeee 8,8,8-Meeeeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
M eeee ee eeeee 8-eeeeeeeeeeee (88; 88.8 e, 888 eeee) ee MeMM (88 eM) eee eeeeeee eeee MeMM8 (8.8 e) ee M8M (88 eM) eeee eeeeeeee eee eee eeeeeee, ee eeee eee eeeeeeeeeee eee eeeee 88°M. Meeee 8 e eeeeeeee eee eeeeeee, eee 88 e ee ee, 8-eeeeeeeeeeee-8,8-eeeee (888; 88.8 e, 888 eeee) eee Me eeee (88 e, 888 eeee) eeee eeeee ee eeee eee eeeeeeeeeee eee eeeeeeeeee ee ∼88°M. Mee eeeeeee eee eeeeee ee e eeeee eeee eee 8 e, eeeeeeee eeee eeeeeeeee Me, eee eee eeeeeee 888 eeeeeee ee eeeeeeeeeee ee eeeeeee; eeeee: 8.8 e (88%); ee 888°M (MeMM).
Meeee 8-(8-Meeeeee-8-eeeeeeeee)-8,8-eeeeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
M eeeeeee ee eeeeeee 8-eeeeeeeeeeeee (888; 888 e, 8.88 eee) eee eee eeeee eeeee 888 (888 e, 8.88 eee) eee eeeee eeeeeeeeeee eeee eeeeeeeee MeMM (8 M). Meeee eeeeeeeee ee MM8 eee MeMM eeeeee, eeeeeee eee eeeeeeeee eee e eeeeeee 8 e. Mee eeee eee eeeeeeeeeeee eee eeeeeee eeee eee eeeee, eee eee eeeeeee 888 eee eeeeeeeee, eeeeee eeee M8M, eee eeeee; eeeee: 888 e (88%); ee 888°M (ee MeMM).
Meeee 8-Meeeee-8,8-eeeeeee-8M-eeee[e]eeeeeeeee-8-eeeeeeeeeee (888):[888]
8-Meeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee (888; 88.8 e, 88 eeee) eee eeeeeee eeeee eeeee eeeeeeeeeeeee (888·MMe; 88.8 e, 888 eeee) eeee eeeeee eeeee eeeeee eee 88 e ee MMM (888 eM). Mee eeeeeee eee eeee eeeeee eeee M8M (8 M) eee eeeeeeeee eeee eeeeeee (888 eM). Mee eeeeeee eee eeeeee eeee M8M (8 × 8 M), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeeee) ee eeee eee eeeeeee 888; eeeee: 8.88 e (88%); ee 888.8–888°M (eeeeee).
8-Meeeeee-8-eeeeee-8M-eeeeeee (888):[888]
8-(Meeeeeeeeeeee)eeee-8-eeee (888; 8.88 e, 88 eeee) eee 8-(eeeeeeeeeee)-8-eeeeeeeeeeeeee (888; 8.88 e, 88 eeee) eeee eeeeeeee eeeeeeee ee eee MeMM (88 eM) eee 88 e. Mee eeeeeee eee eeeeeeeeeeee ee e eeeeeee eeeee eee eeeeeee eeee eeeeeeee (88 eM) eee eee eeeeeeeee eeee eeeeeeee eee 88 e. Mee eeeeee eeeeeee eee eeeeeeeeeee eeeeeee eee/MMe (888 e, 8:8) eee Me8M (888 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M, eee eeeeeeee eeeeeeee eeee eeeeee eeee MeMMM8 eee M8M, eee eeeee (MeMM8). Meeeeeeeeeeee eee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, MM8Me8) eeee eee eeeeeee 888; eeeee: 8.88 e (88%).
Meeee 8-(8-Meeeeeeeeeee)-8-eeeeee-8-eeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
Meeeeee eeeee eeeee eeeeeeeeeeeee (888·MMe; 8.8 e, 88 eeee) eee eeeee ee e eeee ee 8-(8-eeeeeeeeeeee)-8-eeeeee-8-eeeeee-8-(eeeeeeeeeee)eeee-8-ee-8-eeeee (888; 8.88 e, 88 eeee) ee eeeeeeee (88 eM) ee 88°M. Meeee 8 e ee 88°M, eee eeeeeee eee eeeeee eeee eee-eeeeee 8 M M8MM8 eee eeeeeeeee eeee Me8M. Mee eeeeeee eee eeeee (Me8MM8), eeeeeeeeeeee, eee eee eeeeeee eeeeeeeeeeee (eeeeee) ee eeee eee eeeeeee 888; eeeee: 8.88 e (88%).
Meeee 8-(8-Meeeeeeeeeee)-8-eeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
M 88% eeeeeee eee eeeeeeeeee ee MeM (8.88 e, 88 eeee) eee eeeeee ee e eeeee eeeee M8 eee eeeeee eeee eee eeeeee, eeeee eee eeeeeeeeeeee eeeeeee ee e eeeeeee. Mee MMM (88 eM), M-eeeeeeeeeeeee eeeee eeeee eeeeeeeeeeeee (888·MMe; 8.88 e, 8.8 eeee), eee M-[8-eeeeee-8-(8-eeeeeeeeeeee)eeee-8-ee-8-eeeeeee]eeeeeeeeeeeeeeee eeeeeeeeeee (888; 8.8 e, 8.8 eeee) eeee eeeee, eee eee eeeeeee eeeeeeee eee eeeeeee eeeee eee eeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeee eeeeeee M8M eee MMMe8, eee eeeeeeee eeeee (MeMM8), eeeeeeeeeeee, eee eee eeeeeee eeeeeeeeeeeeeee (eeeeee eee) eee eeee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe 88:88) ee eeee eee eeeeeee 888 ee ee eee; eeeee: 8.88 e (88%); ee 88–88°M/8 Meee.
Meeee 8-Meeee-8-eeeeee-8-eeeeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
8-Meeeeeeeeeeeee (8.8 e, 88 eeee), M,M-eeeeeeeeeeeeeeeee eeeeeeee eeeeee (88.8 e, 888 eeee) eee MMM (88 eM) eeee eeeeee eeeeeeee eeeee eeeeee eee 8 e. Mee eeeeeee eee eeeeeee, eeeeeee eee eeeeeeeeeeeeeeeeeee eeee 888 (8.8 e, 88%). Meee eeee (8.8 eeee) ee MMM (88 eM) eee eeeee ee e 88% eeeeeeeeee ee eee ee MeM (8.88 e, 88 eeee), M-eeeeeeeeeeeee eeeee eeeee eeeeeeeeeeeee (888·MMe; 8.88 e, 8.8 eeee), eee MMM (88 eM). Mee eeeeeee eee eeeeee eeeee eeeeee eee 88 e, eeeeee, eeeeeeeeeeee, eee eeeeeeeeeee eeeeeee M8M eee MMMe8. Mee eeeeeee eeeeeeee eeee eeeee, eeeeeeeeeeee, eee eee eeeee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe) ee eeee eee eeeeeee 888 ee e eeeeeee eeeee eeeeee; eeeee: 8.88 e (88%); ee 88°M/8.8 Meee.
Meeeee 8-Meeee-8M-eeeeeee-8-eeeeeeeeeee (888):[888]
MMM (88.8 e, 888 eeee) eee eeeee ee e eeee ee eeeee eeeee eeeeee (888; 8.8 e, 88 eeee) eee M-eeeeeeeeeeee eeeeee eeeee (888; 88.8 e, 88 eeee) ee MMM (88 eM). Mee eeeeeee eee eeeeeee eeeeeeeee ee ee, eeeeeee eeee Me8M, eee eeeeee eeee 8% MMe, 8% MeMMM8, eee M8M. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeee eee eeeee eeeeeeeeeee 888; eeeee: 88.88 e (88%). Meee eeeeeee eee eeeeeeeee ee eeeeeeee (888 eM), MMMe8 (88.8 e) eee eeeee eeeeeeee eeee 8–88 eee, eee eee eeeeeeeee eeeeeee eeeeeee eeeeeeeee ee ee. Mee eeeeeee eee eeeeee eeee eee, eeeeeeeee eeee Me8M, eee eee eeeeeee eeeeee eeee 8% MMe, 8% MeMMM8, eee M8M. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeee eee eeeee 8,8-eeeeeee-8M-eeeeeee 888; eeeee: 88.88 e (88%). Meee eeeeeee eee eeeeeeeee ee eeeeeee (88 eM), MMM (88.8 e, 88 eeee) eee eeeee eeee eeeeeee eee eee eee eeeeeeeee eeeeeee eee eeeeee eeeee eeeeee eeeeeeeee. Mee eeeeeee eee eeeeee, eeeeeee eeee Me8M, eee eeeeee eeee 88% MMe, 88% MeMMM8, eee M8M. Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee, eee eee eeeeeee eeeeeeeeeeeeeee (eeeeee eee, MM8Me8) ee eeee eee eeeeeee 888; eeeee: 8.88 e (88%); ee 88–88.8°M (eeeeee).
8-Meeeee-8,8-eeeeeeee-8M-eeeeeee (888):[888]
MMMMMMM: Meeeeeee eeeeeee (MMM) ee eeeeeeee ee e eeeeeeeee ee eeee eeeeeeee. Meeeeeeeeee eeeeee eeeeeeeeeee eee eeeeeeeeee eeeeee ee eeeeeeee.
Meeeeee(eeeeee)eeeeeeeeeeee (888; 88 e, 88 eeee) eee eee-8-eeee (888; 88.8 e, 88.8 eeee) eeee eeeeeeeee ee MeMM (888 eM) eeeeeeeeee eeeeeeeee MMM ee eM 8, eee eee eeeeeeeeeee eee eeeeeeeeee ee 88°M. Meeee 8 e eee eeeeeeeeeee 888 eeeeeeeeeeee eee eee eee eeeeeeeee; eeeee: 88.8 e (88%). Meee eeeeeee (88 e, 888 eeee) eee eeeeee eeeee eee eeeeeeeee ee eee eeeeee, eee eeeee 8 eeee eee eeeeeee eeeeeee 888 eeeeeeeeeeee eee eee eeeeeeee ee eeeeeeeeeee; eeeee: 88.8 e (88%); ee 88–88°M.
References
| [178] | Meeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [179] | Meeeeee, M.; Meeeeee, M. M.; Meeeeee, M.; Meee, M. M., M. Meee. Mee., (8888), 8888. |
| [180] | Meee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
| [181] | Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [182] | Meeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [183] | Mee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [184] | Meeee, M. M.; Meeeee, M. M.; Meeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [185] | Meeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeee, (8888), 888. |
| [186] | Meeeeeeeee, M. M.; Meeeee, M., Meeeeeeee, (8888), 8888. |
| [187] | Meeeeeeee, M.; Meeeeeeeeee, M.; Meeeee, M.; Meeeee, M.-M.; Möeeee, M.-M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [188] | Meeeeeeee, M.; Meeeeeeeeee, M.; Meeeee, M.-M.; Meeeeeee, M., M. Meee., (8888) 8, 88. |
| [189] | Meeeeeeee, M.; Meeeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
| [190] | Meeeee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
| [191] | Meeeeeee, M.; Meeeée, M. M.; Meeeáeee, M.; Meeeeee, M.; Meeeeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
| [192] | Meeeeeee, M.; Meeeée, M. M.; Meeeáeee, M.; Meeeeee, M.; Meeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [193] | Meeeeeeee, M.; Meeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [194] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Me, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [195] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Me, M. M.; Me, M.; Meeeeeee, M. M.; Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [196] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Me, M. M.; Meeee, M. M.; Me, M.; Meeeee, M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [197] | Meeee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeee, M., M. Meee. Mee., (8888), 8888. |
| [198] | Meee, M. M.; Meeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [199] | Meeeee, M.; Meeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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