Synthesis of Tetrahydroindeno[1,2-b]indol-10-ones and Their Rearrangement to [2]Benzopyrano[4,3-b]indol-5-ones

James L. Bullington; John Harold Dodd

doi:10.1021/jo00070a017

Synthesis of Tetrahydroindeno[1,2-b]indol-10-ones and Their Rearrangement to [2]Benzopyrano[4,3-b]indol-5-ones

James L. Bullington, John Harold Dodd

Chemistry

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

62 Scopus citations

Abstract

The formation of tetrahydroindeno[1,2-b]indol-10-ones 1 by reaction of ninhydrin with substituted anilines is described. The tetrahydroindeno[1,2-6]indol-10-ones 1 rearrange to form 5,11-dihydro-[2]benzopyran[4,3-b] indol-5-ones 8 when heated under acid conditions. Reaction of ninhydrin with 3-hydroxyaniline gave a benzo[b]indeno[2,1-d]furan 4.

Original language	English (US)
Pages (from-to)	4833-4836
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	58
Issue number	18
DOIs	https://doi.org/10.1021/jo00070a017
State	Published - Jan 1 1993

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Organic Chemistry

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10.1021/jo00070a017

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title = "Synthesis of Tetrahydroindeno[1,2-b]indol-10-ones and Their Rearrangement to [2]Benzopyrano[4,3-b]indol-5-ones",

abstract = "The formation of tetrahydroindeno[1,2-b]indol-10-ones 1 by reaction of ninhydrin with substituted anilines is described. The tetrahydroindeno[1,2-6]indol-10-ones 1 rearrange to form 5,11-dihydro-[2]benzopyran[4,3-b] indol-5-ones 8 when heated under acid conditions. Reaction of ninhydrin with 3-hydroxyaniline gave a benzo[b]indeno[2,1-d]furan 4.",

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year = "1993",

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doi = "10.1021/jo00070a017",

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T1 - Synthesis of Tetrahydroindeno[1,2-b]indol-10-ones and Their Rearrangement to [2]Benzopyrano[4,3-b]indol-5-ones

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AU - Dodd, John Harold

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The formation of tetrahydroindeno[1,2-b]indol-10-ones 1 by reaction of ninhydrin with substituted anilines is described. The tetrahydroindeno[1,2-6]indol-10-ones 1 rearrange to form 5,11-dihydro-[2]benzopyran[4,3-b] indol-5-ones 8 when heated under acid conditions. Reaction of ninhydrin with 3-hydroxyaniline gave a benzo[b]indeno[2,1-d]furan 4.

AB - The formation of tetrahydroindeno[1,2-b]indol-10-ones 1 by reaction of ninhydrin with substituted anilines is described. The tetrahydroindeno[1,2-6]indol-10-ones 1 rearrange to form 5,11-dihydro-[2]benzopyran[4,3-b] indol-5-ones 8 when heated under acid conditions. Reaction of ninhydrin with 3-hydroxyaniline gave a benzo[b]indeno[2,1-d]furan 4.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Synthesis of Tetrahydroindeno[1,2-b]indol-10-ones and Their Rearrangement to [2]Benzopyrano[4,3-b]indol-5-ones

Abstract

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