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A simple method for the synthesis of isoindoline derivatives.
- Source :
-
Chemistry of Heterocyclic Compounds . Feb2023, Vol. 59 Issue 1/2, p54-62. 9p. - Publication Year :
- 2023
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00093122
- Volume :
- 59
- Issue :
- 1/2
- Database :
- Academic Search Index
- Journal :
- Chemistry of Heterocyclic Compounds
- Publication Type :
- Academic Journal
- Accession number :
- 163189368
- Full Text :
- https://doi.org/10.1007/s10593-023-03162-6