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Larsen, R. D., Science of Synthesis, (2005) 15, 623.
The reaction of 2-cyanoarylamines 279 with ketones using tin(IV) chloride[55,56,746] or zinc(II) chloride[747] as a Lewis acid catalyst gives quinolin-4-amines 280 (Scheme 99). Cyanoarylamines couple with tetrahydro-2H-pyran-2-one (δ-valerolactone) in the presence of titanium(IV) chloride to afford the corresponding 2,3-dihydropyrano[2,3-b]quinolin-4-amines.[748]
Meeeee 88 Meeeeeee ee 8-Meeeeeeeeeeeeee eeee Meeeeee ee Meeeeee Meeeeeee-8-eeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeee 8-Meeee-8-eeeeeeeeeeeeeee-8-eeeeeeeeeee (888, M8 = M); Meeeeee Meeeeeeee:[88]
8-Meeeeeeeeeeeeeeee (888, M8 = M; 8.88 e, 88 eeee) eee MeMe8 (8.8 eM, 88 eeee) eeee eeeee ee e eeeeeee eeee ee eeeeee eeeeeeeeeeee (8.88 eM, 88 eeee) ee eee eeeeeee (88 eM). Mee eeeeeee eee eeeeeee eeeee M8 ee ee eee 88 eee eee eeee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee eeee eee eeeeeee eee 88 eee eeee eee. ee Me8MM8 (88 eM, eM ~88). Mee eeeeeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM) eee eeeeeeee ee Meeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM) eee eee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeee eeeeee eeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
[55] | Meeeeeee, M. M.; Meeeeeeee, M.; Meeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[56] | Meeeeeee, M. M.; Meeeeeeee, M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[746] | Meeeeee, M.; Meeeeee, M.; Meeee, M., Meeeeee. Meee., (8888) 888, 888. |
[747] | Meeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
[748] | Meeee, M. M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.