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10.23.2.3 Aromatization

DOI: 10.1055/sos-SD-110-01096

Joule, J. A.Science of Synthesis Knowledge Updates, (20182186.

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 PictetSpengler-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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