Beilstein J. Org. Chem.2021,17, 1481–1489, doi:10.3762/bjoc.17.104
affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol
derivatives.
Keywords: 4-aryltetralin-2-ol; 5-aryl-benzo[7]annulen-7-ol; cascade reaction; Prins/Friedel–Crafts; Introduction
2,4-Disubstituted tetralins (Figure 1, 1), especially 2-functionalized tetralins are privileged building blocks for medicinal chemistry applications which are known to exhibit a wide
to 2,4-disubstituted tetralin compounds and thus facilitate their biological investigations.
The cascade Prins/Friedel–Crafts reaction to form multiple chemical bonds in one operation has emerged as an atom-economic and straightforward strategy for the construction of oxygen-containing heterocycles
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Graphical Abstract
Figure 1:
Parent structure of 2,4-disubstituted tetralins (1) and selected medicinally useful derivatives 2–4....
Beilstein J. Org. Chem.2021,17, 932–963, doi:10.3762/bjoc.17.77
subsequent trapping of the carbocation with the bromide ion led to all-cis-2,4,6-trisubstituted tetrahydropyran 297 (Scheme 69).
Lalli and van de Weghe reported a chiral BINOL-derived bisphosphoric acid- and CuCl-catalyzed enantioselective tandem Prins–Friedel–Crafts cyclization between homoallylic alcohol
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Graphical Abstract
Scheme 1:
General strategy for the synthesis of THPs.