2,3-Disubstituted indoles from olefins and hydrazinesvia tandem hydroformylation–Fischer indole synthesis and skeletal rearrangement
Linnepe (née Köhling), Petra; Schmidt, Axel M.; Eilbracht, Peter; Linnepe (née Köhling) Petra; Fachbereich Chemie, Organische Chemie I, Universität Dortmund; Schmidt Axel M.; Fachbereich Chemie, Organische Chemie I, Universität Dortmund; Eilbracht Peter; Fachbereich Chemie, Organische Chemie I, Universität Dortmund
Журнал:
Organic & Biomolecular Chemistry
Дата:
2006
Аннотация:
The tandem hydroformylationâ Fischer indolisation protocol is used in the synthesis of 2,3-disubstituted indoles. After hydroformylation of selected olefins to form α-branched aldehydes in a one-pot procedure these are condensed with phenylhydrazine to give hydrazones. Upon acid-promoted [3,3]-sigmatropic rearrangement indolenine intermediates with quaternary centres in the 3-position are formed, which, after selective Wagnerâ Meerwein-type rearrangement of one of the substituents from the 3- to the 2-position, lead to 2,3-disubstituted indoles. Several olefins, bearing substituents with various functional groups, as well as cyclic olefinic systems are investigated.
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