Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

Fawaz Aldabbagh; W. Russell Bowman; Emma Mann; Alexandra M.Z. Slawin

doi:10.1016/S0040-4020(99)00419-6

Bu₃SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

Fawaz Aldabbagh
, W. Russell Bowman
, Emma Mann
, Alexandra M.Z. Slawin

Loughborough University

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

Abstract

A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu₃SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.

Original language	English
Pages (from-to)	8111-8128
Number of pages	18
Journal	Tetrahedron
Volume	55
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4020(99)00419-6
Publication status	Published - 25 Jun 1999
Externally published	Yes

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title = "Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles",

abstract = "A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.",

author = "Fawaz Aldabbagh and \{Russell Bowman\}, W. and Emma Mann and Slawin, \{Alexandra M.Z.\}",

year = "1999",

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AU - Aldabbagh, Fawaz

AU - Russell Bowman, W.

AU - Mann, Emma

AU - Slawin, Alexandra M.Z.

PY - 1999/6/25

Y1 - 1999/6/25

N2 - A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.

AB - A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.

U2 - 10.1016/S0040-4020(99)00419-6

DO - 10.1016/S0040-4020(99)00419-6

M3 - Article

AN - SCOPUS:0033603409

SN - 0040-4020

VL - 55

SP - 8111

EP - 8128

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

Abstract

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Bu₃SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles