Water‐Based Synthesis of Novel 6, 7‐Dihydrobenzofuran‐4 (5H) ‐Ones

Abstract

A simple, efficient, and high yielding one‐pot protocol for the synthesis of 4‐keto‐4,5,6,7‐tetrahydrobenzofurans has been developed by three‐component coupling reaction of dimedone, phenylglyoxal monohydrate, and heteroaryl amines in eco‐friendly solvent water under reflux conditions. The protocol avoids the use of catalysts, toxic solvents, tedious work‐up procedures, and chromatographic separation. The reaction proceeds at fast rates within 45 min and provides access to a variety of fused‐ring furans in high to excellent yields.

Regioselective Synthesis of 1,6‐Dihydropyrrolo[2,3‐g]indazole Derivatives via Three‐Component Domino Reaction

“…According to Ref. and our previous research, a possible reaction mechanism is proposed for this three‐component domino reaction in Scheme . First, a condensation of arylglyoxals 2 with 5,5‐dimethylcyclohexane‐1,3‐dione 3 occurs to give adduct intermediates A , followed by intermolecular Michael addition of 1 H ‐indazol‐6‐amine 1, to provide intermediates B .…”

“…In recent years, many research groups studied the reaction of the amines, arylglyoxals, and cyclic 1,3‐dicarbonyl compounds for the preparation of novel nitrogen‐containing heterocycles (Scheme a,b) . In 2013, our group described a three‐component reaction of 1 H ‐indazol‐6‐amine, aldehyde, and 1,3‐dicarbonyl compounds in EtOH under catalyst‐free conditions, yielding pyrazolo[3,4‐ a ]acridine derivatives (Scheme c) .…”

Vibrational spectroscopic studies, theoretical aspects, and X‐ray analysis of xanthenodiones (1,8‐dioxooctahydroxanthenes)

“…These compounds are known to have antiproliferative, [ 6 ] leishmanicidal, [ 7 ] antibacterial, [ 8,9 ] and fungicidal [ 10 ] activities. Because of the biological properties presented by xanthenodiones and their applications in photodynamic therapy and laser technology, [ 11,12 ] several synthetic methodologies for their preparation have been described.…”

Rh(II)‐mediated one‐pot synthesis of dihydrobenzofuran and spiro[2.5]oct‐1‐ene: Experimental and DFT studies

“…Therefore, the broad bioactivities and chemical reactivity have stimulated chemists to develop several approaches for constructing dihydrobenzofuran‐4‐one (DBF) and SOE derivatives. [ 25–28 ] However, these synthetic approaches do not explain why the yield percent of DBF dominates over its constitutional isomer SOE. More materially, whether the reaction is thermodynamic or kinetically controlled, DFT calculation predicting the electronic structure, reactivity, and spectroscopic feature of DBF and SOE has not been carried out.…”