Brønsted-acid-catalyzed allylic substitution reactions of the in situ generated 3-hydroxy indanones with alcohols and sulfamides were investigated, which provided a facile route for the synthesis of a large variety of 3-alkoxy and 3-sulfamido indanones. The key intermediates, 3-hydroxy indanones, were obtained through the intramolecular Meyer−Schuster rearrangement of o-propargyl alcohol benzaldehydes. The resulting 3-benzyloxy indanone could be selectively modified by allylic sulfonamidation and reduction reactions.

The one-pot synthesis of dibenzo[a,f]azulen-12-ones has been established starting from o-propargyl alcohol benzaldehydes and alkynes. The key azulenone bicyclic skeletons were formed through intramolecular Meyer-Schuster rearrangement and intermolecular [5+2]-cycloaddition sequence....

A metal-free intramolecular [3+2] cycloaddtion has been achieved by treating benzene-linked propynol-ynes with AcOH/H2O in a one-pot manner. The reaction provides greener, 100% atom-economic, highly regioselective, and more practical access to functionalized naphtho­[1,2-c]­furan-5-ones with valuable and versatile applications. The regioselective α-deuteration of naphtho­[1,2-c]­furan-5-ones has been also presented with excellent deuterium incorporation and chemical yields. Moreover, the fluorescent properties of naphtho­[1,2-c]­furan-5-one products have been investigated in solution.

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