- Diels-Alder Reactivity of Pyranoindol-3-ones, Indole 2,3-Quinodimethane Analogues
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The pyranoindol-3-ones (7) are stable indole-2,3-quinodimethane type dienes, which undergo Diels-Alder reaction with alkynes to give, after loss of carbon dioxide, carbazoles.The reactivity of the diene is increased by the presence of the electron-withdrawing t-butoxycarbonyl group on the indole nitrogen.The pyranoindolones (7) are less reactive, and exhibit the opposite regiochemistry in their Diels-Alder reactions than the isomeric pyranoindol-3-ones (1).Factors which affect the regiochemistry of the Diels-Alder reaction are discussed.
- Moody, Christopher J.,Rahimtoola, Kulsum F.
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p. 673 - 679
(2007/10/02)
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