An easy access to carbazolones and 2,3-disubstituted indoles

Donala Janreddy; Veerababurao Kavala; J. W.John Bosco; Chun Wei Kuo; Ching Fa Yao

doi:10.1002/ejoc.201001357

An easy access to carbazolones and 2,3-disubstituted indoles

Donala Janreddy, Veerababurao Kavala, J. W.John Bosco, Chun Wei Kuo, Ching Fa Yao

Department of Chemistry

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

38 Citations (Scopus)

Abstract

Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives. Synthesis ofderivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation strategy is demonstrated. The starting materials were easily accessed from C-arylation of 1,3-diketones by o-nitroiodobenzenes.

Original language	English
Pages (from-to)	2360-2365
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.201001357
Publication status	Published - 2011 Apr 1

Keywords

Cyclization
Iron
Nitrogen heterocycles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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title = "An easy access to carbazolones and 2,3-disubstituted indoles",

abstract = "Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives. Synthesis ofderivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation strategy is demonstrated. The starting materials were easily accessed from C-arylation of 1,3-diketones by o-nitroiodobenzenes.",

keywords = "Cyclization, Iron, Nitrogen heterocycles",

author = "Donala Janreddy and Veerababurao Kavala and Bosco, {J. W.John} and Kuo, {Chun Wei} and Yao, {Ching Fa}",

year = "2011",

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T1 - An easy access to carbazolones and 2,3-disubstituted indoles

AU - Janreddy, Donala

AU - Kavala, Veerababurao

AU - Bosco, J. W.John

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2011/4/1

Y1 - 2011/4/1

N2 - Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives. Synthesis ofderivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation strategy is demonstrated. The starting materials were easily accessed from C-arylation of 1,3-diketones by o-nitroiodobenzenes.

AB - Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives. Synthesis ofderivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation strategy is demonstrated. The starting materials were easily accessed from C-arylation of 1,3-diketones by o-nitroiodobenzenes.

KW - Cyclization

KW - Iron

KW - Nitrogen heterocycles

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