- Synthesis of new pyrrolo[3,4-b]indol-3-ones as latent substrates for pyrrolo[3,4-b]indoles
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We report the synthesis of new examples of the 1,4-dihydropyrrolo[3,4-b]indol-3(2H)-one ring system via Fischer indolization between the appropriate phenylhydrazines and pyrrolidine-2,3-diones. Lithiation at the C-1 position with lithium diisopropylamide following by quenching with iodomethane affords 1-methyl-1,4-dihydropyrrolo[3,4-b]indol-3(2H)-ones in excellent yield.
- Saulnier, Mark G.,Schreiber, Steven M.,Cavanaugh, Kerri L.,Perni, Robert B.,Joyner, H. Howard,Gribble, Gordon W.
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- A silicon-mediated domino approach to pyrrolidine- and piperidine-2,3-diones
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Lithiated silylthioacetals 1 react with co-bromoalkyl isocyanates 2 via addition to the isocyanate, a 1,3-silyl shift and ringclosure by bromide displacement to give lactams 6. The latent α-oxo group can be liberated by thioacetal cleavage with hypervalen
- Jungf, Alexander,Koch, Oliver,Ries, Monika,Schaumann, Ernst
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- Reaction of Singlet Oxygen with Enamino Carbonyl Systems. A General Method for the Synthesis of α-Keto Derivatives of Lactones, Esters, Amides, Lactams, and Ketones
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A general method for the introduction of a ketone α to the carbonyl group of a ketone, lactone. ester, substituted amide, or lactam has been developed involving the formation and dye-sensitized photooxygenation of enamino carbonyl intermediates.
- Wasserman, Harry H.,Ives, Jeffrey L.
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p. 3573 - 3580
(2007/10/02)
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