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A SIMPLE METHOD FOR THE SYNTHESIS OF ISOINDOLINE DERIVATIVES

Виталий В. Шорохов, Данила С. Лебедев, Максим А. Бойченко, Сергей С. Жохов, Игорь В. Трушков, Ольга А. Иванова
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Abstract


A method for the synthesis of isoindoline derivatives was developed based on a domino reaction involving a donor-acceptor cyclopropane containing a bromomethyl group in the ortho position of the aromatic substituent and structurally varied primary amines (anilines, benzylamines, cycloalkylamines). It was shown that the resulting N-benzyl-1,3-dihydroisoindole under hydrogenolysis conditions at room temperature underwent selective cleavage of the exocyclic N–CH2Ar bond followed by in situ lactamization to form benzo[b]pyrrolizidinone. The same product was obtained in a domino reaction starting with reduction of the azidomethyl group at the ortho position of the donor aromatic substituent. Similarly, the generation of the o-2-aminoethyl group was accompanied by two successive cyclization reactions leading to the formation of benzo[e]indolizidinone.

 


Keywords


anilines; benzo[e]indolizidines; benzo[b]pyrrolizidines; isoindolines; donor-acceptor cyclopropanes; domino reaction.

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