5 research outputs found
Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement
A convenient two-step sequence for the conversion of
alkylidenecycloalkanones
to bromofurans is reported. The steps involve Mg-mediated diastereoselective
dibromocyclopropanation of alkylidenecycloalkanone followed by acidic
alumina-mediated regioselective ring expansion of the cyclopropyl
ketone. The scope of the reaction was investigated using alkylidenecycloalkanones
derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans
fused to various benzocycloalkanes. Representative examples of stereoconvergent
dibromocyclopropanation and total aromatization of the furobenzocycloalkane
are also reported
Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement
A convenient two-step sequence for the conversion of
alkylidenecycloalkanones
to bromofurans is reported. The steps involve Mg-mediated diastereoselective
dibromocyclopropanation of alkylidenecycloalkanone followed by acidic
alumina-mediated regioselective ring expansion of the cyclopropyl
ketone. The scope of the reaction was investigated using alkylidenecycloalkanones
derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans
fused to various benzocycloalkanes. Representative examples of stereoconvergent
dibromocyclopropanation and total aromatization of the furobenzocycloalkane
are also reported
Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement
A convenient two-step sequence for the conversion of
alkylidenecycloalkanones
to bromofurans is reported. The steps involve Mg-mediated diastereoselective
dibromocyclopropanation of alkylidenecycloalkanone followed by acidic
alumina-mediated regioselective ring expansion of the cyclopropyl
ketone. The scope of the reaction was investigated using alkylidenecycloalkanones
derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans
fused to various benzocycloalkanes. Representative examples of stereoconvergent
dibromocyclopropanation and total aromatization of the furobenzocycloalkane
are also reported
Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke–Wilson Rearrangement
A convenient two-step sequence for the conversion of
alkylidenecycloalkanones
to bromofurans is reported. The steps involve Mg-mediated diastereoselective
dibromocyclopropanation of alkylidenecycloalkanone followed by acidic
alumina-mediated regioselective ring expansion of the cyclopropyl
ketone. The scope of the reaction was investigated using alkylidenecycloalkanones
derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans
fused to various benzocycloalkanes. Representative examples of stereoconvergent
dibromocyclopropanation and total aromatization of the furobenzocycloalkane
are also reported
One-Pot Regioselective Synthesis of <i>meta</i>-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles
A highly
efficient one-pot method has been developed for the synthesis
of <i>meta</i>-terphenyls via a regioselective [3 + 3] annulation-elimination
sequence involving Morita–Baylis–Hillman (MBH) acetates
of nitroalkenes and alkylidenemalononitriles. The reaction takes place
in a regioselective manner under mild conditions (Et<sub>3</sub>N,
room temperature) to afford a wide variety of <i>meta</i>-terphenyls bearing aryl, heteroaryl and styrenyl groups. This novel
[3 + 3] annulation takes advantage of the 1,3-bielectrophilic character
of MBH acetates and 1,3-binucleophilic character of alkylidenemalononitriles
and proceeds in a cascade fashion comprising an S<sub>N</sub>2′
substitution, intramolecular 6-<i>endo-trig</i> Michael
addition and double elimination. Representative synthetic transformations
of the products, for instance, to <i>meta</i>-terphenyl
derived isoindolinones have also been demonstrated