Synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles

John M. Gardiner; Andrew D. Goss; Tahir N. Majid; Andrew D. Morley

doi:10.1016/S0040-4039(02)02590-X

Synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles

John M. Gardiner
, Andrew D. Goss
, Tahir N. Majid
, Andrew D. Morley

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

Abstract

Synthesis of two new types of 'head-to-head' N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeric nitroanilines can be intercepted by electrophile trapping of both N-oxybenzimidazole termini to give C2,C2-linked dimers. These represent two regioisomeric motifs constituting new classes of benzimidazole dimers. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	511-513
Number of pages	2
Journal	Tetrahedron Letters
Volume	44
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4039(02)02590-X
Publication status	Published - 13 Jan 2003

Keywords

Alkylation; Cyclocondensation reaction (synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles by base-mediated cyclocondensation of N-alkyl-2-nitroanilines followed by alkylation with biselectrophiles)

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10.1016/S0040-4039(02)02590-X

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title = "Synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles",

abstract = "Synthesis of two new types of 'head-to-head' N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeric nitroanilines can be intercepted by electrophile trapping of both N-oxybenzimidazole termini to give C2,C2-linked dimers. These represent two regioisomeric motifs constituting new classes of benzimidazole dimers. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

keywords = "Alkylation; Cyclocondensation reaction (synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles by base-mediated cyclocondensation of N-alkyl-2-nitroanilines followed by alkylation with biselectrophiles)",

author = "Gardiner, \{John M.\} and Goss, \{Andrew D.\} and Majid, \{Tahir N.\} and Morley, \{Andrew D.\}",

year = "2003",

month = jan,

day = "13",

doi = "10.1016/S0040-4039(02)02590-X",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles

AU - Gardiner, John M.

AU - Goss, Andrew D.

AU - Majid, Tahir N.

AU - Morley, Andrew D.

PY - 2003/1/13

Y1 - 2003/1/13

N2 - Synthesis of two new types of 'head-to-head' N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeric nitroanilines can be intercepted by electrophile trapping of both N-oxybenzimidazole termini to give C2,C2-linked dimers. These represent two regioisomeric motifs constituting new classes of benzimidazole dimers. © 2002 Elsevier Science Ltd. All rights reserved.

AB - Synthesis of two new types of 'head-to-head' N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeric nitroanilines can be intercepted by electrophile trapping of both N-oxybenzimidazole termini to give C2,C2-linked dimers. These represent two regioisomeric motifs constituting new classes of benzimidazole dimers. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Alkylation; Cyclocondensation reaction (synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles by base-mediated cyclocondensation of N-alkyl-2-nitroanilines followed by alkylation with biselectrophiles)

U2 - 10.1016/S0040-4039(02)02590-X

DO - 10.1016/S0040-4039(02)02590-X

M3 - Article

SN - 1873-3581

VL - 44

SP - 511

EP - 513

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Synthesis of novel 2,2- and 1,1-linked dimeric 'head-to-head' N-alkoxybenzimidazoles

Abstract

Keywords

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