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A novel iodine-mediated rearrangement of heterocyclic [3.3.3]propellanes under green conditions is described. This metal-free transformation for the straightforward synthesis of substituted 2-azaanthraquinones proceeds via ring opening/dissociation of C–O and C–N bonds/intramolecular C(sp3)–C(sp3) bond formation/ring expansion/aza-ring closure/1,3-N to N alkyl migration. High atom-efficiency, synthetically useful yields, easily accessible starting materials, and mild reaction conditions are advantages of this process.

A convenient approach for the synthesis of thiazolo[3,4-a]-benzimidazole derivatives has been developed. Three-component reaction of readily available o-phenylenediamines, aryl isothiocyanate, and 4-chloro-3-oxobutanoate in toluene–dichloromethane without any catalyst proceeds under reflux to afford the title compounds in high yields. The structure of the target molecule was confirmed by X-ray diffraction.