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

Takumi Abe; Tomoki Itoh; Tominari Choshi; Satoshi Hibino; Minoru Ishikura

doi:10.1016/j.tetlet.2014.07.113

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

Takumi Abe, Tomoki Itoh, Tominari Choshi, Satoshi Hibino, Minoru Ishikura

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	5268-5270
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2014.07.113
Publication status	Published - Sept 17 2014
Externally published	Yes

Keywords

Dakin oxidation
Indole-3-carbaldehyde
Indolo[2,1-b]quinazoline
Oxidative coupling
Urea hydrogen peroxide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.07.113

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title = "One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde",

abstract = "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.",

keywords = "Dakin oxidation, Indole-3-carbaldehyde, Indolo[2,1-b]quinazoline, Oxidative coupling, Urea hydrogen peroxide",

author = "Takumi Abe and Tomoki Itoh and Tominari Choshi and Satoshi Hibino and Minoru Ishikura",

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T1 - One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

AU - Abe, Takumi

AU - Itoh, Tomoki

AU - Choshi, Tominari

AU - Hibino, Satoshi

AU - Ishikura, Minoru

N1 - Funding Information: This work was supported in part by the Ministry of Education, Culture, Sports, Sciences, and Technology of Japan through a Grant-in Aid for Scientific Research (No. 26460012 ). Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/9/17

Y1 - 2014/9/17

N2 - 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.

AB - 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.

KW - Dakin oxidation

KW - Indole-3-carbaldehyde

KW - Indolo[2,1-b]quinazoline

KW - Oxidative coupling

KW - Urea hydrogen peroxide

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

Keywords

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