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Larsen, R. D.; Cai, D., Science of Synthesis, (2005) 15, 401.
The reaction of (2-acylaryl)amines 47 with activated alkynes 48, e.g. dimethyl acetylenedicarboxylate[132,133] or methyl propynoate,[134] gives the substituted quinolines 49 (Scheme 17). The scope of these studies is limited. Often the aminobenzaldehyde or acetophenone gives only the intermediate β-anilinoacrylate, requiring subsequent heating in methanolic hydrochloric acid[133] or sodium methoxide[135] in a separate step to achieve cyclization. The benzophenones cyclize directly in good yields with dimethyl acetylenedicarboxylate in refluxing benzene,[135] but in poor yields with methyl propynoate in refluxing methanol.[134] Similarly to the reaction of propynoates, 1,3-bis(alkoxycarbonyl)allenes undergo Michael addition with 2-acylanilines followed by condensation through treatment of the adduct with potassium tert-butoxide.[136] The reaction is general for benzaldehyde and aceto- or benzophenones. Acylarylamines 50 couple with ethynylbenzene through a ruthenium-mediated hydroamination and condensation to produce the 4-substituted 2-phenylquinolines 51.[137] A similar zinc-mediated cyclization of 2-(trifluoromethyl)arylamines with terminal alkynes affords 4-(trifluoromethyl)quinolines.[138]
Meeeee 88 Meeeeeee ee (8-Meeeeeee)eeeeee eeee Meeeeee[888,888,888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeeee 8-Meeeeeeeeeeeeee-8,8-eeeeeeeeeeeee (88, M8 = M8 = M; M8 = Me; M8 = MM8Me); Meeeeee Meeeeeeee:[888]
M eeee ee 8-eeeeeeeeeeeeeeeee (88, M8 = M8 = M; M8 = Me; 8.88 eee) eee MMMM (88, M8 = MM8Me; 8.88 eee) ee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeeee eee 88 e eee eeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88%; ee 888–888°M.
8,8-Meeeeeeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeeeeeee eeee ee eeeeeeeee eeeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeee.
M eeeeeee ee eeeeeeeeeeeeeee (8.88 e, 88.8 eeee), 8-eeeeeeeeeeeeeeeee (88, M8 = Me; 8.888 e, 8.8 eeee), [Me8(MM)88] (88.8 ee, 8.888 eeee), 88% ee MMM8 (88 eM, 8.888 eeee), eee eeeeeee (8 eM) eee eeeeeee ee 888°M eee 88 e. M8M eee eeeeeee ee eeeeeeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MM8Me8 8:8) ee eeee eee eeeeeee; eeeee: 8.88 e (>88%).
References
| [132] | Meeeeeeeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [133] | Meeeeeeeeee, M. M.; Meee, M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [134] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [135] | Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [136] | Meeeee, M.; Meeeeeee, M.; Meeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
| [137] | Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [138] | Meeee, M.; Me, M.-M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
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