Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

F  Aldabbagh; W R  Bowman; E  Mann; A M Z  Slawin

Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

F Aldabbagh, W R Bowman, E Mann, A M Z Slawin

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-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.

Original language	English
Pages (from-to)	8111-8128
Number of pages	18
Journal	Tetrahedron
Volume	55
Issue number	26
Publication status	Published - 25 Jun 1999

Keywords

SUBSTITUTION SRN1 REACTIONS
ADDITION-REACTIONS
1,2-FUSED INDOLES
BUTYLTIN HYDRIDE
PYRIDINIUM RINGS
CYCLIZATION
ROUTE
ALKYLATIONS
ALKALOIDS
SULFIDES

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@article{467d3b7a150e44ce914645c48d29112e,

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-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.",

keywords = "SUBSTITUTION SRN1 REACTIONS, ADDITION-REACTIONS, 1,2-FUSED INDOLES, BUTYLTIN HYDRIDE, PYRIDINIUM RINGS, CYCLIZATION, ROUTE, ALKYLATIONS, ALKALOIDS, SULFIDES",

author = "F Aldabbagh and Bowman, {W R} and E Mann and Slawin, {A M Z}",

year = "1999",

month = jun,

day = "25",

language = "English",

volume = "55",

pages = "8111--8128",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "26",

}

TY - JOUR

T1 - Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

AU - Aldabbagh, F

AU - Bowman, W R

AU - Mann, E

AU - Slawin, A 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-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.

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-(omega-bromoalkyl) or N-[omega-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regioselective radical cyclisation onto the azole rings followed by oxidative re-aromatisation, (C) 1999 Elsevier Science Ltd. Ail rights reserved.

KW - SUBSTITUTION SRN1 REACTIONS

KW - ADDITION-REACTIONS

KW - 1,2-FUSED INDOLES

KW - BUTYLTIN HYDRIDE

KW - PYRIDINIUM RINGS

KW - CYCLIZATION

KW - ROUTE

KW - ALKYLATIONS

KW - ALKALOIDS

KW - SULFIDES

M3 - Article

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

Keywords

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