What question did this study set out to answer?

The aim was to create new compounds with allomaltol and pyridazine, and to investigate their light-based reactions.

March 26, 2026Organic & Biomolecular Chemistry0 citations

Synthesis of allomaltol containing pyridazines and their photochemical transformation into substituted benzo h pyrano2,3- f cinnolin-8-ones

AMAlexander V. Migulin CMConstantine V. Milyutin AKAndrey N. Komogortsev

Key Points

The aim was to create new compounds with allomaltol and pyridazine, and to investigate their light-based reactions.
Developed a two-step synthesis approach for terarylenes with allomaltol and pyridazine.
Reacted methylene-active allomaltol derivatives with aromatic arylglyoxals.
Condensed the resulting diaroylethene with hydrazine.
The synthesized terarylenes did not show photochemical transformations under UV light.
Acylation of the hydroxyl group enabled 6π-electrocyclization during photoreactions.
Acylated precursors showed potential as effective photoacid generators.

Abstract

In this study, we developed an efficient two-step approach for the synthesis of novel terarylenes featuring an allomaltol substituent and a pyridazine bridge and investigated their photochemical behavior. The proposed strategy is based on the initial reaction of methylene-active allomaltol derivatives with aromatic arylglyoxals, followed by condensation of the resulting diaroylethene with hydrazine. It was found that the obtained terarylenes do not undergo any photochemical transformations under UV irradiation. However, modification of the hydroxyl group through acylation overcomes this limitation and directs the photoreaction toward 6π-electrocyclization. This study provides a convenient method for accessing previously unknown benzohpyrano2,3-fcinnolin-8-one derivatives and demonstrates that their acylated precursors can serve as efficient photoacid generators.

Ask AI

Helpful

Bookmark

View Full Paper