Efficient one-pot synthesis of dithieno(dibenzothieno)-fused cycloheptanones, tropones, and cyclooctanonesстатья
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Аннотация:The reactions of alpha,beta-unsaturated amide/triflic anhydride complexes (generated in situ from the corresponding amides and triflic anhydride) with dithiophenes and dithienylmethanes proceed as tandem alkylation-Vilsmeier-Haack acylation to form dithieno- and dibenzothieno-fused cycloheptanones and cyclooctanones in moderate to good yields. The reactions of 2-bromo-N,N-dimethylacrylamide/triflic anhydride complex allow preparation of tropones in a simple one-pot procedure. The reaction of 2,2-dibenzothienylmethane with dimethylacrylamide/triflic anhydride complex proceeds unusually to afford dimethylaminonaphthalene in addition to the predictable fused cyclooctanone.