The invention discloses a preparation method of 2-aza [5]
helicene, and belongs to the field of
organic synthesis. The preparation method comprises the following steps: firstly, taking commercialized 2, 3-dihydrophenanthrene-4 (1H)-
ketone as an initial
raw material, and generating a 4-bromo-1, 2-dihydrophenanthrene-3-
formaldehyde compound through a Vilsmeier-Haack reaction; secondly, the 4-bromo-1, 2-dihydrophenanthrene-3-
formaldehyde and the 2, 3-dichloro-5, 6-dicyanobenzoquinone are subjected to oxidative
aromatization, and a 4-bromophenanthrene-3-
formaldehyde compound is generated; then, a Suzuki
coupling reaction is catalyzed through
palladium, and
axial chirality 4-(4-methylpyridine-3-yl)
phenanthrene-3-formaldehyde is constructed; and finally, carrying out intramolecular
Aldol condensation / cyclization reaction to realize'shaft-to-screw 'transfer, so as to successfully obtain the target product 2-aza [5]
helicene. The raw materials adopted by the method are cheap and easy to obtain, and the synthesis method is simple to operate and meets the requirements of industrial production.