The indol(in)e building block is one of the “privileged-structures” for the pharmaceutical industry since this fragment plays a central role in drug discovery. While the electron-rich character of the indole...
The electrophilicity of 4 different 3–nitroindole derivatives has been evaluated by Mayr’s free linear energy relationship (log k(20 °C) = sN (E + N)) and reveals unexpected values for aromatic...
The novel nucleophilic activation of enolizable unsaturated ketones allows their addition to nitroaromatics and furnishes the corresponding formal dearomatized (4+2) cycloadducts.
Simple nitroarenes such as nitronaphthalenes and nitroquinolines smoothly undergo dearomatizing [4+2] cycloadditions with silyloxydienes under 16 kbar. Highly functionalized 3-dimensional polycyclic adducts bearing a tetrasubstituted carbon centre at the ring...
Indoles substituted by electron-depleted thio groups at positions 1 and 3 react as C2=C3 dipolarophiles with an electron-rich azomethine ylide dipole under flow conditions. The dearomatizing (3+2) cycloadditions readily occur to afford the corresponding fluorinated 3Dpyrrolidinoindolines bearing a tetrasusbtituted carbon centre at the ring junction.
Indoles, benzofurans and benzothiophenes substituted by a cyano group at positions 2 or 3 are shown to behave differently toward azomethine ylide 1,3‐dipole 1, in (3+2) cycloadditions. While the C2=C3 aromatic double bond of 3‐cyanoheteroarene reacts as dipolarophile to generate the corresponding dearomatized cycloadducts, the C≡N bond of 2‐cyanobenzofuran reveals more reactive and imidazoline are obtained in this case. 2‐Cyanoindole substituted by an electron‐withdrawing triflyl group on the nitrogen atom allows the formation of the bis‐cycloadduct where the C=C and C≡N moieties both reacted. The C≡N vs C=C reactivity is nicely supported by DFT computations.
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