Issue 3, 1990
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Diels–Alder reactivity of pyrano[4,3-b]indol-3-ones, indole 2,3-quinodimethane analogues

Christopher J. Moody  and  Kulsum F. Rahimtoola  

Abstract

The pyrano[4,3-b]indol-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 pyrano[3,4-b]indol-3-ones (1). Factors which affect the regiochemistry of the Diels–Alder reaction are discussed.

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Article information

DOI
https://doi.org/10.1039/P19900000673
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 673-679

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Diels–Alder reactivity of pyrano[4,3-b]indol-3-ones, indole 2,3-quinodimethane analogues

C. J. Moody and K. F. Rahimtoola, J. Chem. Soc., Perkin Trans. 1, 1990, 673 DOI: 10.1039/P19900000673

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