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Joule, J. A., Science of Synthesis Knowledge Updates, (2018) 2, 1.
General Introduction
The four isomeric pyrido[X,Y-b]indoles are most frequently referred to as “carbolines”, thus 9H-pyrido[2,3-b]indole (1) is α-carboline, 9H-pyrido[3,4-b]indole (2) is β-carboline, 5H-pyrido[4,3-b]indole (3) is γ-carboline, and 5H-pyrido[3,2-b]indole (4) is δ-carboline (Scheme 1).
Meeeee 8 Meeeeeeeee, Meeee, eee Meeeeeeee ee eee Meeeee[M,M-e]eeeeeee (Meeeeeeeee)
Mee eeee “eeeeeeeee” eee eeeeee ee M. M. Meeeee Me. eee Meeeee Meeeeeee[8] eeeeee eeeee eeee ee eee eeeeeeeeee eeeeeeeeeee ee eee eeeeeee eeeeeeeee, e.e. eeeeeee (88; eee eeeee), eee eee eeeeee ee eeeeeeee eee eeeeeeeeee eeeeeeeeee eeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeee eee eeeeeeeee ee eee eeee eee eeeeeeeeeeee ee eee eeeee; ee eee eeee eeeeeeeeeeee eee eeeee eeeeeee eeee eeeeeeeeeeee ee eeeeeeee eee eeeeeeee ee eee eeeeeeee eeee eeeeeeee. Mee eee eeeeeeeeee eee eeeeee, eeeeeeeee, eeeeee eeeeeeee eeeeee eeee eeeeeee eeeeee ee eee eeeee ee 888–888 °M.
Meeee eee eeee e eee eeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeee: α-eeeeeeeee eeeeeeeee,[8] α-, γ-, eee δ-eeeeeeeee eeeeeeeeee,[8] α-, γ-, eee δ-eeeeeeeee eeeeeeeee,[8] β-eeeeeeeeee ee eeeeeeeee eeeeeeeeeeeee,[8] γ-eeeeeeeeee,[8] β-eeeeeeeee eeeeeeeee,[8] eeeeeeeeee (eeeeee β-eeeeeeeeee eee eeeeee eeeeeee eeeeeeeeeee),[8] eee eeeeeeeeee.[8]
Me eeee ee eee eeeeeeeeee, eee eeeeeee eeeeeeeeee ee e eeeeeeee eeee eeeeeeee eee ee eeeeee/eeeeeee eeee M-eeeeeeee eee ee eeeeeeeee eee eee eeeeeeeeeee ee Meeeee 8 eeeee eee β-eeeeee. Meee, eeeeeeee eeee ee eeeee eeeeee eeeee eeeeee ee e eeeeeeeeee (eeeeeeeeeee) eeee (e.e., 8),[88,88] eeeeeee ee eeeee e eeeeee eeee ee eeeeeeeeeee eee M-eeeeeeee, eee eeee eeeeeeee eeee ee eeeee eeeeee, eeeeee eeeeeeee eeeeeeeeee ee eeeeeeee, eeeeee eee eeeeeee 8.[88,88]
Meeeee 8 Meeeeeeeee ee eee Meeeeeee eee Meeeee Meeeeeeee ee β-Meeeeeeee[88–88]
Mee eeeeeeeeee ee eee eeeeeeee eeee eeeeeeeee eeeeeeee ee eee eMe eeeeee ee eeeee eeeeeeeee eeeee ee eeeee eee eeeee ee Meeee 8.[88,88] Mee eeeeeeeee ee eee M-eeeeeeeee, eeeeeeee ee eeeee eMe eeeeee, eee eeeee ee Meeee 8.[8,88] Mee eee eeeeeee eeeee eeeeee eeee eee eMe eee eee eeeeeeee-eeee eeeeeeee ee eeeeeeeeeeee (8.8) eee eee eMe eee eee eeeeee M-eeeeeeee (88.8).
Meeee 8 eMe Meeeee ee Meeeeeee Meee Meeeeeeee ee Meeeeeeeee[88–88]
Meeeeeee | eMe (M8M) | Mee |
---|---|---|
8 | 8.8 | [88] |
8 | 8.8 (8.8)e | [88,88] |
8 | 8.8 | [88] |
8 | 8.8 | [88] |
eeeeeeeeeeee | 8.8 | [88] |
e Mee eee eeeeeeeeee eeeee eeee eeeeeeee eeeeeeeee eeeeee eee eee eMe.
Meeee 8 eMe Meeeee ee M-Meeeeeeee ee Meeeeeeeee[88,88]
Meeeeeee | eMe (M8M) | Mee |
---|---|---|
8 | 88.8 | [88] |
8 | 88.8 | [88,88] |
8 | 88.8 | [88] |
8 | 88.8 | [88] |
eeeeee | 88.8 | [88] |
Mee M-eeeeeeeee ee eeeeeeeeeee eeeee eee eeee eeeeee (Meeee 8).[88,88] Meeee eeeeeee eeeeeee eee eeeeeeeee ee “eeeeeeeeeee eeeee”, e.e. ee eee γ-eeeeee 8-eeeeee-8M-eeeeee[8,8-e]eeeeee 8 eeee 8-eeeeee-8M-eeeeee[8,8-e]eeeee-8-eee eeee 8 (Meeeee 8). Mee eeeeee-eeeeee eeeeeeeeeee eeeee eee ee eeeeeeee;[88–88] eeeeeee eee eeeeeee eeeeeeeee eeeee eeeeeeeeee ee eeeee eeeeeeeeee, eeee 8M eee 8M eee 8.
Meeee 8 eMe Meeeee ee eee M-Meeeeeeee ee Meeeeeee-M-eeeeee Meeeeeeeeee Meeee[88,88]
Meeeeeee | eMe (M8M) | Mee |
---|---|---|
8.88 (8.8)e | [88,88] | |
88.8 (88.8)e | [88,88] | |
88.8 | [88] | |
88.8 | [88] |
e Mee eee eeeeeeeeee eeeee eeee eeeeeeee eeeeeeeee eeeeee eee eee eMe.
Meeeee 8 Meeeeeeee ee ee Meeeeeeeeee Meee eeee γ-Meeeeeeeeee Meeeee[88–88]
Meeeeeeeeee eeeee eeee ee 8 eeeee eeee eeeee eeeeeee ee eee eeee-eeeeeeee eeee eeeeeeee ee eeee eeeeeeeeeee eeeee (e.e., 88) eeee eeeee eee M-eeeeeeeee eeeeeeeee (e.e., 8) eee ee eeeeeeee ee eeeeeeeeeeeee ee eeeeee eeeeeee (Meeeee 8).[88–88]
Meeeee 8 Meeeeeeee ee ee Meeeeeeeeee Meee eeee e β-Meeeeeeeeee Meeeee, Mee Meeeeeee eeee Meeeeeeeeee, eee Meeeeeeeeeeee ee e β-Meeeeeeeeee Meeeeeeeee[88–88]
Mee eeeeeeeeeee eeeee eee ee eeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeeeee eeee ee eeee eeeeeeeeee eeeeeeeeeee eeeee eeeeee eeeeeeeeeee. Mee eeeeeee, 8-eeeeee-8M-eeeeee[8,8-e]eeeee-8-eee eeeeee (8) ee eeeeeee ee 8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeeee[8,8-e]eeeeee (88) ee 88% eeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeeee ee 8-Meeeee-8M-eeeeee[8,8-e]eeeee-8-eee Meeeee eeee 8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeee[8,8-e]eeeeee[88]
Mee eeee ee eeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee ee eeeeeeeeee eeeee. Mee ee eeee eee eeeeeeee eeee ee eee eeeeeee eeee eeeeee eeee ee eee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeee ee ee.
Mee 88M eee 8M MMM eeeeeee ee eee eeee eeeeeeeee eeeeeee eee eeeeeeeeee ee Meeeee 8.[88,88]
Meeeee 8 88M (88.8 MMe) eee 8M (888.8 MMe) MMM Meeeee eee Meeeeeee Meeeeeeee eee eee Meee Meeeeeeeee ee MMMM-e8[88,88]
β-Meeeeeeee eeeee eeeee eeeeeeeee ee eeeeeee eeeeee eeeeeeeee eeeeeee ee eeeeeeeeee eeee eeeeeee (88) eeee Meeeeee eeeeeee eee eeeeeeeee[88,88] eee eeeeeeeeee (88) eeee Meeeeeeeee eeeeeeeee[88] eeeeeee eee β-eeeeeeeeeee-eeeeeeeeee eeeeeeeeeeeeee (88) eeee Meeeeeeeeeeee eeeeeeee[88] ee eee eeee eeeee eeeeee ee eeeeeeeee eeee eeeeeee e 8,8,8,8-eeeeeeeeee-β-eeeeeeeee eeee,[88–88] eeeeeeeee (88)[88–88] eeee Meeeeeeeeeeee eeeeeee eee ee eeeeeeeeee eeeeeee (Meeeee 8). Mee eeeeeeeee ee eeeeeeeeee eeee e eeeeeee eeeee eeeeeeee eeee eeee ee 88 eee eee eeeeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeee eee eee eeeeeee ee eeee eeeeeee (eeeeee ee ee eee ee eeeeeee eeeeeeeeee eee eeee ee eeeee eeeeeeee eeeeeee ee eeeeeeeeeeeeeee). Meeeeeeeeeee (88) eeee Meeeeeeeeeee eeeeeeeeee eee eeeeeeeeeee eeeeeeee eeeeeee eeeeeeeeeeeee M, eee eee eeee eeeeeeee.[88] Meeeeeeee M (88) ee eee eeeeeeee ee e eeeeee ee eeeeeeeee eeeeee eeeeeeeee eeeeeeee eeee Meeeeeee eeeeee eeeeeee;[88] eee eeeeee eeee eee eeee e β-eeeeeeeee eeee eee eeee e eeee eeeeeee M8 eeeeeeeeeee.
Meeeee 8 Meeeeeeee Meeee ee Meeeeee Meeeeeee[88–88]
Me eeeeeeeeee, eeeee eee eeee e eee eeeeeee eeeeeeeeee eeeeeeeeee eee ee eee eeeee eeeeeeeee eeeeeee. α-Meeeeeeee-eeeeeeeeee eeeeeeeeeeee-8 (88) eee eeeeeeee eeee Meeeeeeee eeeeeeeeeee eee ee eeeeeeeee.[88] Meeeeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee (88), eeeeeee α-eeeeeeeee, eeeee eeeeeeee e-eeeeeeeee eeeeeeee.[88]
Meeeeeeeeeeee (88)[88] eee eeeeeeeeeeeeee (88; eeee Meeeeeee eeeeeee)[88] eeee eeeee ee eeeeeee eeee β-eeeeeeeee eeeeeeeee eeeeeeeeee (88) eee eeeeeeeeeee (88; eeee eeeeeeee eee eeeee Meeeee eeeeeee).[88] δ-Meeeeeeee-eeeeeeeeee eeeeeeeeeeee (88) eee eee γ-eeeeee eeeeeeeeeeeeeee (88) eee eee ee eeeeeee eeeeeeeee eeee Meeeeeeeeee eeeeeeeeeeeee. Meeeeeeeeeee eee eeeeeeeeeeeeeee eeee eeeeeeeeeeee eeeeeeeeee.[88] Mee eeeeeeeee ee eeeeeee eeee e eeeeeee eeeee eeeeeeee eeee, eeee ee 88 eee 88, ee eee eeeeeee ee eeee eeeeeee.
References
[1] | Meeeee, M. M.; Meeeeeee, M., M. Meee. Mee., (8888) 888, 888. |
[2] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Mee. M. Mee. Meee., (8888) 88, 888. |
[3] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Meeee. Meee. M. (Meee. Meeeee.), (8888) 88, 888. |
[4] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Meeee. Meee. M. (Meee. Meeeee.), (8888) 88, 888. |
[5] | Meeíeeeee, M.; Méeee-Meeeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
[6] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M., Meee. Meeeeeeeee. Meeee. (Meee. Meeeee.), (8888) 88, 888. |
[7] | Meee, M. M., Mee. Meee. Meeeee. Mee., (8888) 88, 8. |
[8] | Meeeeeeeeee, M. M.; Meeeeee, M. M., Mee. Meeeeeeeee. Meee., (8888) 8, 88. |
[9] | Meeeeee, M. M.; MeMeee, M. M., Me Meeeeeeeeeee Meeeeeeee, Meeeeeeeee, M. M., Me., Meeee: Mee Meee, (8888); Mee. 8, e. 888. |
[10] | Meee, M.; Meeeeeeee, M.-M.; Meeee, M.; Meeeeeeee, M.; Müeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[11] | Meee, M. M.; Meüeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeee, M. M.; Meeeeeeeeeee, M.; Meeeeeee, M., Mee. Meee., (8888) 8, 888. |
[12] | Meeee, M.; Mee, M.; Mee, M.; Me, M.; Mee, M.; Meee, M.; Me, M.; Meee, M.; Mee, M.; Mee, M., Mee. M. Mee. Meee., (8888) 88, 88. |
[13] | Mee, M.; Meee, M.; Mee, M.; Meee, M.; Meee, M.; Me, M.; Meee, M.; Me, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[14] | Meeeee, M.; Meeeeee, M.; Meeeeeeeee, M. M.; Meñee, M. M.; Meeeeeee, M.; Meeeee, M. M.; Meeóe, M., M. Mee. Meee., (8888) 88, 8888. |
[15] | Meee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meeeeeeee., (8888) 88, 888. |
[16] | Meeeee, M., Me Meeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M., Me.; Meeeeeee Meeee: Mee Meee, (8888); Mee 8, eeeeeee 8. |
[17] | Möeeeee, Me., M. Meeeeeeeeee., (8888) 88, 888. |
[18] | Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[19] | Meeeeeeeeee, M. M.; Meeee, M. M. M.; Meeeeeeee, M. M., Mee. M. Meee., (8888) 88, 8888. |
[20] | Mee Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeeeáeee, M.; Máeeee, M.; Meeeèee, M.; Meeeeeee, M.; Meeeee, M.; Meee, M.; Mee, M.; Meee, M.; Meeóe, M.; Meeee, M.; Meee, M.; Meee, M. M. M.; Meeeeee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[21] | Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeïe, M.; Meeeeeee, M.; Meéeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M.; Meéeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
[22] | Meeeeee, M. M., M. Meee. Mee., (8888), 8888. |
[23] | Meee, M. M.; Meeeee, M. M.; MeMeeeeee, M., M. Meee. Mee., (8888), 8888. |
[24] | Meee, M. M. M.; Meeeeeee, M., M. Meee. Mee., (8888), 8888. |
[25] | Meee, M.; Meeee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 88, 8888. |
[26] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeee, M.; Meeee, M. M., Meee. Meeee. Meee., (8888) 88, 8888. |
[27] | Meeee, M.; Meeeeee, M.; Meeeee, M.; Meéeeeeee, M., Meeeeeeeeee, (8888) 88, 88. |
[28] | Meeeee, M.; Mee-Meee, M., Meeeeeeeeeee, (8888) 8, 888. |
[29] | Meeee, M. M. M.; Meeeeeeee, M. M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[30] | Meeeeeeee, M. M. M., M. Mee. Meee., (8888) 88, 888. |
[31] | Meeeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[32] | Meeeee, M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M.; Meeeee, M. M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[33] | Meeeeeeeee, M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[34] | Meeeee, M. M. M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[35] | Meáeeee, M.; Meeeeó, M.; Meeee, M.; Möeeeee, M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeeeee, Meeeee, M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 88, 888. |
[36] | Meeeeeee, M. M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 88, e 888. |
[37] | Meeeee, M.-M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeeeee, Meeeee, M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 88, e 8. |
[38] | Meeeee, M. M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 8. |
[39] | Meeeee, M. M. M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeee, Meeeee, M. M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 88. |
[40] | Meeeee, M. M.; Meee, M. M.; Meeeeee, M. M.; Meeee, M. M.; M’Meeeee, M. M.; Meeeeeeee, M. M., M. Meeeeeee., (8888) 88, 888. |
[41] | Meeee, M.; Meee, M.; Meeeeee, M. M.; Meeeeeeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[42] | Meeeee-Meeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[43] | Mee, M.-M.; Meee-ee, M.; Meeeeeee, M.; Meeeeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[44] | Meeeee, M.; Meeee, M., Me Mee Meeeeeeee: Meeeeeeee eee Meeeeeeeeeee, Meeeee, M., Me.; Meeeeeee: Mee Meeee, (8888); Mee. 88, ee 888. |
[45] | Meeeáčeeeá, M.; Meeeeee, M.; Meeěšeeeeá, M.; Šeeeeee, M.; Šeeáeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
[46] | Meeeeeee, M. M. M., M. Meee. Mee. M, (8888), 8888. |
[47] | Meeeeeee, M.; Meeeeeeeeeeee, M.; Meeeeeeeee, M.; Meeeee, M.; Meeeéeee, M.; Meeeeeee, M.; Meeeeee, M.; Meee, M.; Meeeeee, M.-M., Meeeeeeee. Mee., (8888) 88, 888. |