HETEROCYCLES

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■ Novel Synthesis of 1,4-Phenylene Bridged Bis-Heterocyclic Tropone Compounds

Yang Li, Feng Li, and Wentao Gao*

*Institute of Superfine Chemicals, School of Chemistry and Chemical Engineering, Bohai University, 19 Keji Road, Jinzhou 121000, China

Abstract

A facile synthesis of novel 1,4-phenylene bridged bis-isoxazolo-, pyrazolo-, and pyrano-fused tropone compounds (2-6) is described, involving the cyclization reaction of 3,3’-{1,4-phenylenebis[(1E)-3-oxoprop-1-ene-1,3-diyl]} bis(tropolone) (1) with hydroxylamine hydrochloride, aromatic hydrazine hydrochlorides, and I2/DMSO/H2SO4 system, respectively. The substrate 1 was obtained via the Claisen-Schmidt condensation reaction between 3-acetyl-tropolone and terephthalaldehyde.