A Mechanistically Deceiving Formation of Aryl(1-indanyl)ketones via Acid-Catalyzed Cyclization of -Alkynylarylmethanols.

The generation of reactive carbocation intermediates from -alkynylarylmethanol substrates was utilized as a means for the synthesis of aryl(1-indanyl)ketones . Substrates with a tertiary carbon at the β-position to the arene generated a carbocation intermediate via dehydration/protonation, followed by cyclization and hydration to give indanylketone products. For substrates with a quaternary carbon at that position, a carbocation intermediate was generated by protonation/elimination of water, followed by a 1,2-shift and a subsequent cyclization/hydration to give highly substituted indanylketones.

Synthesis of Naphtho[2,3-]oxazoles via Ag(I) Acid-Mediated Oxazole-Benzannulation of -Alkynylamidoarylketones.

A cascade oxazole-benzannulation for the synthesis of naphtho[2,3-]oxazoles has been developed employing -alkynylamidoarylketones as substrates. This procedure provides the advantage of preparing a wide variety of substituents on naphtho[2,3-]oxazole structures. In addition, -alkynylamidoarylketones could be prepared from easily accessible and a wide variety of commercially available starting materials.