Heterocycles · 1993 · 19 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryOrganometallic ChemistrySynthetic Medicinal ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryMetal CatalysisTemplate-directed SynthesisHeterocycle FunctionalizationRegioselective SynthesisStereoselective Cross-couplingTransition Metal-catalyzed SynthesisTransition-metal-catalyzed Cross-couplingTransition-metal-catalyzed FunctionalizationTransition-metal-catalyzed Heterocycle SynthesisUllmann Coupling
The cyclic heterobiaryls (3) containing a thenoyl or furoyl group were synthesized in good yields by regioselective acylations of salicyl alcohol (I), followed by the intramolecular Ullmann coupling reaction of the diesters (2).The cleavage of the two ester bonds of 3 by hydrogenolysis or nucleophilic substitution reactions proceeded regioselectively to afford the highly functionalized unsymmehical heterobiaryls (4-6) in good yields.