Issue 0, 1985

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

Abstract

The pyrano[3,4-b] indol-3-ones (13a,b), stable synthetic analogues of indole-2,3-quinodimethanes, undergo Diels–Alder reactions with acetylenes to give, with concomitant loss of carbon dioxide, carbazoles. Thus, reaction with dimethyl acetylenedicarboxylate and dibenzoylacetylene gives the carbazole diesters (15a,c) and dibenzoylcarbazoles (15b,d) respectively. The dibenzoylcarbazoles (15b,d) react with hydrazine to give pyridazo[4,5-b]carbazoles (16). The pyranoindolones (13) also react with benzyne to give the benzo[b]carbazoles (18).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1985, 2505-2508

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

C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1985, 2505 DOI: 10.1039/P19850002505

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements