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Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of ?-Imino Carbenes to Troger Bases.

ABSTRACT: Polycyclic indoline-benzodiazepines can be accessed through the intermolecular reaction of Tröger bases with N-sulfonyl-1,2,3-triazoles. Under RhII catalysis, ?-imino carbenes are generated and a subsequent cascade of [1,2]-Stevens, Friedel-Crafts, Grob, and aminal formation reactions yield the polycyclic heterocycles as single isomers (d.r.>49:1, four stereocenters including two bridgehead N?atoms). Further ring expansion by insertion of a second ?-imino carbene leads to elaborated polycyclic 9-membered-ring triazonanes.

SUBMITTER: Bosmani A

PROVIDER: S-EPMC6033154 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases.

Bosmani Alessandro A Guarnieri-Ibáñez Alejandro A Goudedranche Sébastien S Besnard Céline C Lacour Jérôme J

Angewandte Chemie (International ed. in English) 20180514 24

Polycyclic indoline-benzodiazepines can be accessed through the intermolecular reaction of Tröger bases with N-sulfonyl-1,2,3-triazoles. Under RhII catalysis, α-imino carbenes are generated and a subsequent cascade of [1,2]-Stevens, Friedel-Crafts, Grob, and aminal formation reactions yield the polycyclic heterocycles as single isomers (d.r.>49:1, four stereocenters including two bridgehead N atoms). Further ring expansion by insertion of a second α-imino carbene leads to elaborated p ...[more]

PMID: 29673027

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