One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidati...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 38; pp. 5268 - 5270
Main Authors Abe, Takumi, Itoh, Tomoki, Choshi, Tominari, Hibino, Satoshi, Ishikura, Minoru
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.09.2014
Elsevier
Subjects
Chemistry
Chemistry, Organic
Dakin oxidation
Indole-3-carbaldehyde
Indolo[2,1-b]quinazoline
Oxidative coupling
Physical Sciences
Science & Technology
Urea hydrogen peroxide
Indolo[2,1-b]quinazoline
Urea hydrogen peroxide
Indole-3-carbaldehyde
Dakin oxidation
Oxidative coupling
ANALOGS
CANDIDINE
AGENTS
DERIVATIVES
INDOLES
ALKALOIDS
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Summary:A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidation, and further oxidation/cyclization steps.
Bibliography:KAKEN
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.07.113