Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

Eoin M. Moriarty; Fawaz Aldabbagh

doi:10.1016/j.tetlet.2009.07.023

Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

Eoin M. Moriarty
, Fawaz Aldabbagh

National University of Ireland

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

Abstract

The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of σ-aryl radicals generated from 1-allyl-2-(ω-bromoaryl)benzimidazoles. Inclusion of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequinones, a unique family of potential bioreductive anti-cancer agents.

Original language	English
Pages (from-to)	5251-5253
Journal	Tetrahedron Letters
Volume	50
Issue number	37
Early online date	9 Jul 2009
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.023
Publication status	Published - 16 Sept 2009
Externally published	Yes

Keywords

Annulations
Diazoles
Heterocycles
Quinones

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title = "Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations",

abstract = "The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of σ-aryl radicals generated from 1-allyl-2-(ω-bromoaryl)benzimidazoles. Inclusion of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequinones, a unique family of potential bioreductive anti-cancer agents.",

keywords = "Annulations, Diazoles, Heterocycles, Quinones",

author = "Moriarty, \{Eoin M.\} and Fawaz Aldabbagh",

year = "2009",

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doi = "10.1016/j.tetlet.2009.07.023",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

AU - Moriarty, Eoin M.

AU - Aldabbagh, Fawaz

PY - 2009/9/16

Y1 - 2009/9/16

N2 - The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of σ-aryl radicals generated from 1-allyl-2-(ω-bromoaryl)benzimidazoles. Inclusion of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequinones, a unique family of potential bioreductive anti-cancer agents.

AB - The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of σ-aryl radicals generated from 1-allyl-2-(ω-bromoaryl)benzimidazoles. Inclusion of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequinones, a unique family of potential bioreductive anti-cancer agents.

KW - Annulations

KW - Diazoles

KW - Heterocycles

KW - Quinones

U2 - 10.1016/j.tetlet.2009.07.023

DO - 10.1016/j.tetlet.2009.07.023

M3 - Article

SN - 0040-4039

VL - 50

SP - 5251

EP - 5253

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

Abstract

Keywords

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