Novel benzothiophene 1,1-dioxide deoxygenation path for the microwave-assisted synthesis of substituted benzothiophene-fused pyrrole derivatives.
The reaction of C-(4-substituted-phenyl)-N-(benzoyl)-N-methylglycines with benzo[b]thiophene 1,1-dioxide unexpectedly gave benzothiophene-fused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metal-free Pummerer-type sulfone deoxygenation path. In order to obtain the desired sulfone derivatives, the sulfide group underwent oxidation with m-CPBA to afford sulfones. The structures of all the new products were elucidated by spectroscopic/physical methods and, in two cases, by X-ray diffraction.
Department of Chemistry, Faculty of Science & Literature, Abant İzzet Baysal University, TR14280, Bolu, Turkey.
Hamza
H
Karakuş
Department of Chemistry, Faculty of Science & Literature, Abant İzzet Baysal University, TR14280, Bolu, Turkey. yasardurust@ibu.edu.tr.
Yaşar
Y
Dürüst
D060326:Chemistry Techniques, Synthetic; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry*
D011758:Pyrroles; D013876:Thiophenes; C088015:benzothiophene; D010100:Oxygen
Benzothiophene; Cycloaddition; Heterocyclization; Microwave synthesis; Pyrrole; Sulfone deoxygenation
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