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Issue 31, 2016
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Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles

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Abstract

We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.

Graphical abstract: Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles

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Publication details

The article was received on 14 Jan 2016, accepted on 15 Mar 2016 and first published on 15 Mar 2016


Article type: Communication
DOI: 10.1039/C6CC00365F
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Citation: Chem. Commun., 2016,52, 5443-5446
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    Synthesis of benzofuro[3,2-b]indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles

    T. Tomakinian, R. Guillot, C. Kouklovsky and G. Vincent, Chem. Commun., 2016, 52, 5443
    DOI: 10.1039/C6CC00365F

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