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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 661.
General Introduction
Isoquinoline, a sweet-smelling, low-melting solid (mp 27°C) was first obtained in 1885 by careful separation from quinoline derived from coal tar and, once its constitution was established by oxidation to a mixture of phthalic acid and pyridine-3,4-dicarboxylic acid, named “isoquinoline”,[1,2] quinoline having been isolated, structurally identified, and named some thirty years earlier. The isoquinoline nucleus occurs, mainly at the 1,2,3,4-tetrahydro-level, in a large number of alkaloids;[3–9] the opium poppy alkaloids papaverine (1) and, in more elaborated form, morphine (2) are examples. Emetine (3), with two tetrahydroisoquinoline units, is an amebicide (Scheme 1).
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Mee eeeeeeeeeeee eeeeeee eee eeee eeee eeeeeeeeee ee e eeeeee ee eeeeee eeeeeee eeeeeeee, eeee eeee eeeeeeeeeee eeeeeeeeee eeeeeeee:[88] eeeeeeee eeeeeee eeeeeeeeee M (8), eee ee e eeeeee ee eeeeeeeeeee eeee e eeeeeeeeeee eeeeeee, eeee ee eeeee eeee eeeeeeeee ee eeeeeeeeeee eeeeeeeeee eeee eeeeeeeeeeeee, eee eeeeeeeeeeeee 888 (MM 888) (8), eeeee eee eeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee eeeee eeeeee eee eeeeeee eeeeeeeee. MM 888 (8) eee eeeeeeee eeee e Meeeeeeee eeeeeeee eee ee ee eeee eeeee eeeeeeee eeeeee ee ee eeeeeeeeee eeee (Meeeee 8).
Meeeee 8 Mee Meeeeeeeeeee-Meeeeeeeee Meeeee Meeeeee Meeeeeee
Mee eeeeeeeeee eeeeeeeee ee eeeeeeeeeeee (8) ee eeeee ee Meeeee 8. Mee MM eeeeeeeeee ee eee 88π-eeeeeeee eeeeeeee eeeeee ee eeeeeeeeeeee ee eeeeeeeeeee ee eeee eeeeeeeee eee eeeeeeeeeee, λeee (ε) 888 (8888), 888 (8888), eee 888 (88,888) eee eeeee e eeeeeeeeeeee eeeee ee eeee eeeeeeee, λeee 888, 888, eee 888, eeeeeeeeeeeee ee eeeeeeeee ee eee 8M-eeeeeeeeeeeeee eeeeee, 8.
Meeeee 8 Meeeeeeeee Meeeeeeee ee Meeeeeeeeeee
Mee eeeeeeee-eeeeeeeeeee eeeee eeeeeeee eee e eeeeeeeeeee eeeeee ee eee MMM eeeeeeee eeeeee ee eee eeeeee eeeeeeeee eee eeeeeee (Meeeee 8). 8M,8M-Meeeeeee eeeeeeeee eee eeeeeeeeeeee eee: M8,8 ~ 8; M8,8 = < 8.8; M8,8 = 8.8; M8,8 ~ 8.8; M8,8 = 8.8; M8,8 = 8.8; M8,8 = 8.8; M8,8 = 8.8; M8,8 = 8.8; M8,8 = 8.8 Me.
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Mee eeeeeeeee ee eeeeeeeeeeeee eee eeee eeeeeeeeee eeee eeeee: eeeeeeeeeeeee eeeeeeeee eeeeeee Meeeee–Meee, M 8e,[88] eeeee eeeeeee ee Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee eeeeee,[88–88] Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee,[88,88] eee eeee ee eeeeeee eee, e eeeeeee ee eee eeeeeeeee eeeeee Meeeeeeeeeee Meeeeeeee.[88]
Meeeeeeeeeee, eeee eeeee eeeeeee eee eeeeeeee eeeee, eeeeeeee eeeeeeee eeeeeeeeee eeeeeeeeee eeee eeee ee eee eeeeeeeeee eeeeeeeeee. Meeeeeeeeeee eeeee eeeee ee eeeeeeeeeee ee eee eeeeeeee, eee eMe ee 8.8 eeeeeee ee ee ee eeee eeeeeee ee eeeeeeee (8.8) ee eeee eeeeeee. Me eeeeee eeeeeee eeee eeeee eeeeeee eeeeeeeeee 8-eeeeeeeeeeeeeeeeeee eeeee. Meeeeeeeeeeee eeeeeeeeeeee ee eeeeee eeeee eeeee ee eee eeeeeee eeee, ee M8 ee eeee 8 eee M8 ee eeee 8, eeee eee eeeeee eeeeeeeeeeeee (Meeeee 8).[88] Meeee eee eeee eeeeeeee ee eeeeeeeeeeeee eeeeeeeeeeee ee M8 eeeeee 88, eee eeeee eeeeeeeee eeeeeee e eeeeeeeeee eeeeeee eeeeeeee ee eeeeeeeeeeeee, eee eee eeee eeeee eeeeeeeee ee ee eeeeeee 88, eee eeeeeeeeeeee eeeeeeee ee M8, eeee eeeeeeeeee eeeeeeeeeeeee eeeeee ee eee β-eeeeeeee (M8) ee eee eeeeeee, eee eeee eeeeeeeeeeeeeee (Meeeee 8).
Meeeee 8 Meeeeeee ee Meeeeeeeeeeee Meeeeeeeeeee ee Meeeeeeeeeee
Meeeeeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeee eeee ee M8. Mee eeeeeee eeeeeeee ee e eeeeeeeeeee ee eeeeeeeeeeee eeeeee eeee eee eeeeeeee, eeeeeeeeeeeeee ee eeee eee eeeeeeeeeeee eeeeeee e eeeeeeee eeeeeee eeee; eeeee eeeee, eee eeeeeee, eeee eeee ee −88°M.[88] Meeeeeee ee eeee M8 eee M8 eee ee eeeeeeeeee eeeeee eeeeeeeee ee eeeeeeeeeeee, eee eeee eeeeeeeeeeee ee M8 eeeee eeeeeeeeeeeee eeeeee eeee ee M8.[88] Meee eee ee eeeeeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeee (eee ee eeeeeeeeeee, ee eee eeeeeeeeee eeeeeeeeee eeeeeee ee eeee) eeeee 88, eeee eeeeee ee M8, ee eeeeeeeeeeeee eeee eeee eeeeeeeeee ee eeeeeeeee eeee 88, eeee eeeeee ee M8 (Meeeee 8). M eeeeeeeee ee eee eeeeeeee eeee eeee eeeee eeeeeeeeeeee eeeeeeee eeeeee ee eeee eeeee–eeeeeee eeeeeeee eeeeeeeee eeeee eeeeeeeeeeeee eeee ee ee eeeeeeeee ee eee eeeeeeeeeeee, ee eeeee ee eeeee eeeeeeeeeeee eeeeeeeee. Mee eeeeeeeeeeeeeee eeeeeee 8- eee 8-eeeeeeeeeeeeeeeee eeeeeee eeee eeee eeeeeeeee(8)-eeeeeeeee eeeeeeeee; 8,8-eeeeeeeeeeeeeeeeeee eeeee eeee ee M8.[88,88] Meeeeee eeeeeeeeeeee ee eeeeee eeeeeeee ee eeee eeeeeeeee eee M8.[88,88] Meeeeee, eeeee ee e eeeeeeeeeeee eeeeeeeeee ee eee eeeeeee ee eee eeeeeee ee eee eeeeee eeeee ee e 8-eeeeeeeeeeeeeeeeee eeeeee e 8-eeeeeeeeeeeeeeeeee. Meeeeeee eeee eee eeeeeeee α ee e eeeeeeee eeee eeeeeeee, eeee eee 8-eeeeee eeeeeee eeee eeeeeeeeeeeee eeeeeeee eeeeeee.
Meeeee 8 Meee ee Meeeeeeeeeee Meeeeeeeeeee ee Meeeeeeeeeeeeeeee
Mee eeeeeeeeeeeeeeeee eee eeeeeeee eeee eeeee eeee eeeeeeeeeeee eeeeee, eeeeeeeeeee ee eee eeee eeeeeeee; eee eeee eeeee ee eeeeeeeeeee-8-eeeee (eMe 8.8). Mee eeeeeeeeeeeeeee ee eeeeeeeeeeee-8-eeeeeeeeee eeee, ee e 8-eeeeeee-8-eeeeeeeeeeeeeeeeeeee eeee,[88] eee eee eeeeeeee ee eee eeeeeeeee eeeee eeee e eeeeeeeeeeee, eeeee ee eee Meeeeee eeeeeeee,[88] eee eeee eeeeee eeeeeeeee; ee eeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeee-8-eeeeeeeeee eeeee eeee eeee eeeeeeee. Meeeeeeee eeeeeeeee eeeeeeeeeeee 8-eeeee ee eeeee ee eeeeeeeeeeee ee eeeee ee eeeeee, eeeeeeee ee e eeeeeeeeeee ee eeeeee ee eeee eeeeeeeeeee eeeeeeeeeeeee 88, eee eeee eeeeeeeeeee eeeeeeeeeeee e eeeee eeeeeeee eeeeee, eeeeee eeee ee 8-eeeeeeeeeee eeeeeeeeeeeee 88 (Meeeee 8).
Meeeee 8 Meeeeeeeeeee ee 8-Meeeeeeeeeee Meeee M-Meeeee
Meeeeeee eeeeeeeee e.e. 88,[88] eeeeeee eeeeee ee eee eeeeeeee ee ee eeeeeeeee ee eeeeeeeeeeeee eeeee ee eeeeeeee eee eeee eeeeeee ee M8, eee eeeeee 8,8-eeeeeeeeeeeeeeeeeeee eee eee ee eeeeeeee ee eeeeeeeee (Meeeee 8). Meeee eeeeeeeeee ee eeeeee eeeee ee eee eeeeeee ee eee eeeeeeeee M8-eeeeeeee eee eee eeeeeeee ee eeeee 88 eeee eeeeeeeeeeeee eeeeee 88, eeeeeeee ee eeeeeee ee eee eeeeeeee eeeeeeeeeee eee eeeeeee eee eee eeeeeeeeeeee ee ee eeeeeeee eeeeeeeeeeee 88 eee eeeeeeeeeee ee M8.
Meeeee 8 Meeeeeeeeeee ee 8-Meeeeeeeeeee Meeee Meeeeeee Meeeeeeee
References
[1] | Meeeeeeeeee, M.; eee Meee, M. M., Meee. Meee. Meee. Meee-Mee, (8888) 8, 888. |
[2] | Meeeeeeeeee, M.; eee Meee, M. M., Meee. Meee. Meee. Meee-Mee, (8888) 8, 888. |
[3] | Meeee, M. M. M., Me Mee Meeeeeeee. Meeeeeeee eee Meeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[4] | Meeeee, M., Me Mee Meeeeeeee. Meeeeeeee eee Meeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[5] | Meeee, M., Me Mee Meeeeeeee. Meeeeeeee eee Meeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[6] | Meeeeeeöe, M., Me Mee Meeeeeeee. Meeeeeeee eee Meeeeee, Meeeee, M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 88, e 888. |
[7] | Meeeeeee, M., Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeee: Meeeeeeee, (8888). |
[8] | Meeeee, M., Mee Meeeeeeeeeee Meeeeeeee, Meeeeeee: Mee Meee, (8888). |
[9] | Meeeeeeeee, M. M., Mee Meeeeeeee eee Meeeeeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeee: Meeeeeeeee, (8888). |
[10] | Meeee, M. M.; Meeeeeee, M. M., Meee. Mee., (8888) 888, 8888. |
[11] | Meeeeee, M., Me Meeeee–Meee, (8888); Mee. M 8e/8, e 888. |
[12] | Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M.; Meeeee, M. M., Mee.; Meeee: Mee Meee, (8888); Mee. 88, Meee 8. |
[13] | Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M.; Meeeee, M. M., Mee.; Meeee: Mee Meee, (8888); Mee. 88, Meee 8. |
[14] | Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M.; Meeeee, M. M., Mee.; Meeee: Mee Meee, (8888); Mee. 88, Meee 8. |
[15] | Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8. |
[16] | Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee MM, Meeeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8. |
[17] | Meeeeee, M. M., Me Meeeeeeeeeee Meeeeeeee, Meeeeeeeee, M. M., Me.; Meeee: Mee Meee, (8888); Mee. 8, e 888. |
[18] | Meeeeee, M.; Meeeeeeee, M. M.; Mee, M. M., M. Meee. Mee. M, (8888), 8. |
[19] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M.; Meee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[20] | Meeeeee, M.; Meäeee, M., Meee. Mee., (8888) 888, 8888. |
[21] | Meee, M.; Meee, M.; Meeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[22] | Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[23] | Meeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[24] | Meeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeee, M.; Meeeeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
[25] | Meeee, M.; Meeeeee, M., Meeeee Meeeeee Mee. Meee., (8888), 88. |
[26] | Meeee, M.; Meeeeee, M. Me., M. Meee. Mee., (8888), 8888. |
[27] | Meee, M. M.; Mee, M. M., Meeeeeeeeeee, (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.