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CYCLOISOMERIZATION – A STRAIGHTFORWARD WAY TO BENZO[h]QUINOLINES AND BENZO[c]ACRIDINES

Mikhail Anatoljevich Kuznetsov, Alena Sergeevna Pankova, Aleksandr Nikolaevich Shestakov
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Abstract


Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]acridines. Substituent at the triple bond governs a choice between transition metal or Brønsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the ortho-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.

Keywords


alkynes, benzo[c]acridines, benzo[h]quinolines, pyridines, quinolines, cycloisomerization, synthetic methods

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