Access to aromatic ring–fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Joanne M. O’Connell; Eoin M. Moriarty; Fawaz Aldabbagh

doi:10.1055/s-0032-1316775

Access to aromatic ring–fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Joanne M. O’Connell
, Eoin M. Moriarty
, Fawaz Aldabbagh

National University of Ireland

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

Abstract

Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.

Original language	English
Pages (from-to)	3371-3377
Number of pages	7
Journal	Synthesis
Volume	44
Issue number	21
DOIs	https://doi.org/10.1055/s-0032-1316775
Publication status	Published - 31 Aug 2012
Externally published	Yes

Keywords

cyclization
diazoles
heterocycles
nucleophilic aromatic substitution
radical reaction

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10.1055/s-0032-1316775Licence: Other

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title = "Access to aromatic ring–fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical",

abstract = "Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.",

keywords = "cyclization, diazoles, heterocycles, nucleophilic aromatic substitution, radical reaction",

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doi = "10.1055/s-0032-1316775",

language = "English",

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T1 - Access to aromatic ring–fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

AU - O’Connell, Joanne M.

AU - Moriarty, Eoin M.

AU - Aldabbagh, Fawaz

PY - 2012/8/31

Y1 - 2012/8/31

N2 - Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.

AB - Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.

KW - cyclization

KW - diazoles

KW - heterocycles

KW - nucleophilic aromatic substitution

KW - radical reaction

U2 - 10.1055/s-0032-1316775

DO - 10.1055/s-0032-1316775

M3 - Article

SN - 0039-7881

VL - 44

SP - 3371

EP - 3377

JO - Synthesis

JF - Synthesis

IS - 21

ER -

Access to aromatic ring–fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Abstract

Keywords

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