Novel benzothiophene 1,1-dioxide deoxygenation path for the microwave-assisted synthesis of substituted benzothiophene-fused pyrrole derivatives

Karakuş, HamzaDürüst, Yaşar2021-06-232021-06-2320171381-19911573-501Xhttps://doi.org/10.1007/s11030-016-9700-0https://hdl.handle.net/20.500.12491/9301The 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. [GRAPHICS]eninfo:eu-repo/semantics/closedAccessCycloadditionSulfone DeoxygenationBenzothiophenePyrroleMicrowave synthesisHeterocyclizationNovel benzothiophene 1,1-dioxide deoxygenation path for the microwave-assisted synthesis of substituted benzothiophene-fused pyrrole derivativesArticle10.1007/s11030-016-9700-02115360276777362-s2.0-84988735453Q2WOS:000394440900005Q2