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- W2000387966 abstract "The cycloaddition between N-protected 3-{1-[(trimethylsilyl)oxy]ethenyl}-1H-indoles and substituted maleimides (= 1H-pyrrole-2,5-diones) yielded substituted pyrrolo[3,4-a]carbazole derivatives bearing an additional succinimide (= pyrrolidine-2,5-dione) moiety either at C(5a) or C(10b) depending on the type of the protection group at the indole N-atom. Derivatives substituted at C(10b) were isolated when the protection group, Me3Si or Boc (tBuOCO), was eliminated during the reaction (Schemes 2 and 3), whereas a substitution at C(5a) was observed when an electron-withdrawing group, Tos (4-MeC6H4SO2) or pivaloyl (Me3CCO), was not eliminated (Scheme 1). Complex results were found in reactions between 1-(trimethylsilyl)-3-{1-[(trimethylsilyl)oxy]ethenyl}-1H-indole, in contrast to formerly reported results (Scheme 3). Some derivatives of 1H,5H-[1,2,4]triazolo[1′,2 : 1,2]pyridazino[3,4-b]indole-1,3(2H)-dione were obtained from reactions with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (Scheme 2). All structures were established by spectroscopic data, by calculations, and one representative structure was confirmed by an X-ray crystallographic analysis (Fig.). Finally, the formation of the different structure types was discussed, and compared with similar reactions reported in the literature." @default.
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- W2000387966 date "2005-11-01" @default.
- W2000387966 modified "2023-09-24" @default.
- W2000387966 title "Synthesis of Substituted Pyrrolo[3,4-a]carbazoles" @default.
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- W2000387966 doi "https://doi.org/10.1002/hlca.200590231" @default.
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