Abstract: 2-Substituted benzo[b]thiophene S-oxides have been prepared from the respective benzo[
b]thiophenes by oxidation with meta-chloroperoxybenzoic acid in the presence of BF3
.Et2O and have been
submitted to cycloaddition reactions with alkenes and alkynes.
Keywords: benzo[b[thiophene, benzo[b]thiophene S-oxide, Diels-Alder reaction, cycloaddition.
[1] T. Thiemann, K. Arima, K. Kumazoe, and S. Mataka, Benzothiophene-S-oxides – an overview, Reports of the Institute of Advanced
Material Study, 14, 2000, 139-142; Chem. Abstr., 134, 2001, 326318a.
[2] F. Sagardia, J. J. Rigau, A. Martinez-Lahoz, F. Fuentes, C. Lopez, and W. Flores, Degradation of benzothiophene and related compounds
by a soil Pseudomonas in an oil-aqueous environment, Applied Microbiology, 29, 1975, 722-725.
[3] P. Martin and A. Mendez, Mechanisms of gasoline deposit formation in engine induction systems. Characterization of product
reaction between benzothiophene oxides and benzothiophenes, Petroleum Science and Technology, 15, 1997, 1-15.
[4] A. D. Palkowitz, A. L. Glasebrook, K. J. Trasher, K. L. Hauser, L. L. Short, D. L. Philipps, B. S. Muehl, M. Sato, P. K. Shetler, G.
J. Cullinan, T. R. Pell, and H. U. Bryant, Discovery and synthesis of [6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-
hydroxyphenyl)]benzo[b]thiophene, Journal of Medicinal Chemistry, 40, 1997, 1407-1416.
[5] H. J. Shrives, J. A. Fernandez-Salas, C. Hedtke, A. P. Pulis and D. J. Procter, Regioselective synthesis of C-3 alkylated and arylated
benzothiophenes, Nature Communications, 8, 2012, 14801..