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Schmidt, A., Science of Synthesis, (2004) 19, 135.
Quinoline, isoquinoline, and phthalazine react with potassium cyanide in the presence of benzoyl chloride, undergoing addition to the 1,2-double bond in such a way that the nitrogen atom is benzoylated and the sp3-hybridized α-position bears the cyanide group;[10] however, the Reissert reaction does not proceed with pyridine.[11] The treatment of isoquinolines such as 7 with tosyl chloride and potassium cyanide in a two-phase dichloromethane/water system gives the isolable Reissert compounds, i.e. 2-tosyl-1,2-dihydroisoquinoline-1-carbonitriles.[12–14] Treatment of the crude Reissert compound with a mild base such as 1,8-diazabicyclo[5.4.0.]undec-7-ene, N,N-diisopropylethylamine, or potassium tert-butoxide affords the isoquinoline-1-carbonitriles 8 in good overall yields (Scheme 4).[15] Similarly, the cyanation of quinoline gives quinoline-2-carbonitriles. A related procedure uses 1-alkylquinolinium iodides, which undergo addition of the cyanide to the 4-position at temperatures above −20°C. Oxidation with iodine gives 4-cyano-1-methylquinolinium triiodide.[16]
Meeeee 8 Meeeeeeee ee Meeeeeeeeeee-8-eeeeeeeeeeeee[88]
M8 | M8 | M8 | M8 | 8ee Meee | 8ee Meee | Meeee (%) | Mee | |
---|---|---|---|---|---|---|---|---|
Meee (e) | Meee | Meee, Meee | ||||||
M | M | M | M | 88 | MMM | 8°M, 8 e | 88 | [88] |
MMe | MMe | MMe | M | 88 | MMM | ee, 8 e | 88 | [88] |
MMe | MMe | MMe | Me | 8 | e-MeMM | ee, 8 e | 88 | [88] |
MMe | MMe | MMe | Me | 88 | MMM | 8°M, 8 e | 88 | [88] |
MMe | MMe | MMe | Me | 88 | MMM | ee, 88 e | 88 | [88] |
MMe | MMe | MMe | MM8MM8Me | 88 | MMM | ee, 8 e | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee (8, M8 = M8 = M8 = MMe; M8 = M); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
M eeee ee 8,8,8-eeeeeeeeeeeeeeeeeeeeee (8, M8 = M8 = M8 = MMe; M8 = M; 888 ee, 8.88 eeee) eee MeMe (888 ee, 8.88 eeee, 8.8 eeeee) ee MM8Me8 (88 eM) eee eeeeeeee eeee e eeee ee MMM (888 ee, 88.8 eeee, 8 eeeee) ee M8M (88 eM). Mee eeeeeee eee eeeeeee eeeeeeeeee ee ee eee 88 e. Mee eeee eee eeee eeeeee eeee M8M, eeeeeeeee eeee MM8Me8 (8 × 88 eM), eee eee eeeeeeee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eee eeeeeeeee ee eeeee MMM (88 eM) eee eeeeeee eeee MMM (8.88 eM, 8.8 eeee, 8.8 eeeee) eeeee ee eeeee eeeeeeeeee. Meeee 8 e ee ee eee eeeeeee eee eeeeeee eeee eee. MM8Me, eeeeee eeee M8M, eeeeeeeee eeee MeMMe, eee eee eeeeeeee eeee eeeee (MeMM8). Mee eeeee eeeeeee eee eeee eeeeeeeeeeeeeee (MMMM, MeMMe/eeeeee) ee eeeee eeeeeeeee eeeeee; eeeee: 888 ee (88%).
References
[10] | Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[11] | Meeeeeeeeeeee, M.; Meeeeeeeeeeee, M.; Meee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[12] | Meeee, M. M.; Meeeee, M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[13] | Meeee, M. M.; Meeeee, M.; Meee, M. M., Meee. Mee. (Meeeee), (8888), 888. |
[14] | Meee, M. M.; Meeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[15] | Meeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[16] | Meeeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 8888. |