A general
strategy for the synthesis of indolyl cyclopropanecarbaldehydes
and ketones via a Brønsted acid-catalyzed indole nucleophilic
addition/ring-contraction reaction sequence has been exploited. The
procedure leads to a wide panel of cyclopropyl carbonyl compounds
in generally high yields with a broad substrate scope.
A series of 6-aryl
coumarin dyes were synthesized in satisfactory
yields by Pd-catalyzed Suzuki cross-coupling reactions with a panel
of boronic acids and coumarin bromides. Photophysical studies highlighted
a large Stoke shift and interesting fluorescence quantum yield for
these compounds. Optical properties were also investigated with the
aid of quantum chemical calculations. The treatment of selected coumarin
dyes with increasing amounts of trifluoroacetic acid showed that their
fluorescence can be strongly influenced by pH (fluorescence quenching
at high acid concentrations), while the addition of Fe
3+
and Al
3+
metal ions allowed to highlight dichotomous
behavior with the corresponding reduction in fluorescence with the
increase of [Fe
3+
] or [Al
3+
]. Finally, biological
assays and fluorescence microscopy imaging investigations indicated
that these compounds can be used as potential biomarkers in living
and fixed cells.
A unified protocol for the construction of 3-(2bromoethyl)benzofurans and 2-(benzofuran-3-yl)ethylamines from bis[(trimethylsilyl)oxy]cyclobutene has been developed. This mild and facile strategy was applied for the synthesis of a series of 5-HT serotonin receptor agonists, underlining its potential for the syntheses of bioactive compounds and natural products.
The reaction between configurably stable -lithiated oxiranes (and aziridines) and 3-substituted cyclobutanones allows to obtain enantiomerically enriched cyclobutanols (er > 98:2). These adducts, subjected to base-mediated Payne rearrangement lead to...
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