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DDQ dehydrogenative Diels-Alder reaction for the synthesis of functionalized spiro[carbazole-1,3′-indolines] and spiro[carbazole-1,5′-pyrimidines]
Ist Teil von
New journal of chemistry, 2021-08, Vol.45 (34), p.15423-15428
Ort / Verlag
Cambridge: Royal Society of Chemistry
Erscheinungsjahr
2021
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
DDQ promoted the reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with 3-methyleneoxindoles in refluxing ethanol resulting in functionalized dihydrospiro[carbazole-1,3′-indolines] in good yields and with high diastereoselectivity. Similar reactions with 5-arylidene-1,3-dimethylbarbituric acids also afforded functionalized spiro[carbazole-1,5′-pyrimidines] in satisfactory yields. The reaction actually proceeded
via
the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their sequential Diels-Alder reaction with dienophiles and further isomerization process. DFT calculations showed that the Diels-Alder reaction has a normal electron-demanding character.
Reactive 3-vinylindoles were generated by
in situ
DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones, and underwent sequential Diels-Alder reaction to give novel heterocyclic spirocarbazoles.