Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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The oxidation of indole derivatives using dimethyl dioxirane

Marçal*, Luisa L. ; Garden, Simon J. ;

Abstract:

The oxidation of indoles is an important route for the formation of oxindoles. Popular methods employ DMSO/HCl, N-halosuccinimides or t-BuOCl. Additionally, 2,3-disubstituted indoles undergo oxidative rearrangement to give spiro-pyrrolidine-2- oxindoles, a heterocyclic framework found in natural products and some currently interesting pharmaceutical compounds. The present study has investigated the use of dimethyl dioxirane (DMD) as an agent for promoting the oxidative rearrangement of tetrahydro-β- carbolines to spiro-pyrrolidine-2-oxindoles.

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Palavras-chave: Tryptophan, Pictet-Spengler, spiro-pyrrolidine-2-oxindole,

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013819112854

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Como citar:

Marçal*, Luisa L.; Garden, Simon J.; "The oxidation of indole derivatives using dimethyl dioxirane", p. 167 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_2013819112854

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