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Joule, J. A., Science of Synthesis Knowledge Updates, (2018) 2, 186.
The 14π electron system of 9H-pyrido[3,4-b]indoles makes dehydrogenative aromatization of partially reduced precursors straightforward. Accordingly, because the assembly of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoles via Pictet–Spengler-type reactions [see Science of Synthesis, Vol. 15 (Section 15.5.1.1.1.2.3.2)] of tryptamines with aldehydes (see examples in Schemes 163 and 164, Section 10.23.2.1.2.1.2.3.1.1; see also Section 10.23.2.3.1) is so easy, the dehydrogenation route to fully aromatic 9H-pyrido[3,4-b]indoles is much more important for these carboline isomers than for the other three. This approach to 9H-pyrido[3,4-b]indoles has been by far the most frequently used of all methods to this carboline isomer and there is a great deal of duplication in the literature.
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M8 | M8 | M8 | Meeee (%) | Mee |
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Me | M | M | 88 | [888] |
8-M8MM8M8 | M | M | 88 | [888] |
8-MM8M8 | M | M | 88 | [888] |
8-MeMM8M8 | M | M | 88 | [888] |
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8-eeeeeee | M | M | 88 | [888] |
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(MM8)8Me | M | M | 88 | [888] |
8-M8MM8M8 | MM | M | 88 | [888] |
Me | M | MM8Me | 88 | [888] |
8-M8MM8M8 | M | MM8Me | 88 | [888] |
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References
[248] | Meeeeeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeee-Meeeeee, M.; Meeeeee-Meeeeeeeee, M.-M.; Máeeeee-Möeeee, M.; Meeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[249] | Meee, M.-M.; Meee, M.-M.; Me, M., MMM Mee., (8888) 8, 88 888. |
[250] | Meeeeeeee, M.; Meeee, M. M.; Meeeeee, M.; Meeeeee, M. M.; Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88 888. |