Synthesis of structurally diverse benzimidazolyl benzimidazolones by application of soluble polymer support

Hsia Yuan Chen; Manohar V. Kulkarni; Chih Hau Chen; Chung-Ming Sun

doi:10.1016/j.tet.2008.04.081

Synthesis of structurally diverse benzimidazolyl benzimidazolones by application of soluble polymer support

Hsia Yuan Chen, Manohar V. Kulkarni, Chih Hau Chen, Chung-Ming Sun^*

^*Corresponding author for this work

National Chiao Tung University

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

13 Scopus citations

Abstract

Chemical stability and reactivity of a bifunctional polymer conjugate containing an ortho-amino arylamide linkage have been successfully exploited to achieve a parallel synthesis of methoxycarbonylated head-tail bis-benzimidazoles. Regioselective alkylation of the two nitrogens in the benzimidazolone moiety has been carried out by ipso-fluoro displacement, and N-alkylation to generate two diversities. Cleavage of the polymer support has resulted in two libraries of di- and tri-substituted benzimidazolyl benzimidazolones in high purity and high yield. All reaction steps have been monitored by ¹H NMR on the support directly.

Original language	English
Pages (from-to)	6387-6394
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	27
DOIs	https://doi.org/10.1016/j.tet.2008.04.081
State	Published - 30 Jun 2008

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title = "Synthesis of structurally diverse benzimidazolyl benzimidazolones by application of soluble polymer support",

abstract = "Chemical stability and reactivity of a bifunctional polymer conjugate containing an ortho-amino arylamide linkage have been successfully exploited to achieve a parallel synthesis of methoxycarbonylated head-tail bis-benzimidazoles. Regioselective alkylation of the two nitrogens in the benzimidazolone moiety has been carried out by ipso-fluoro displacement, and N-alkylation to generate two diversities. Cleavage of the polymer support has resulted in two libraries of di- and tri-substituted benzimidazolyl benzimidazolones in high purity and high yield. All reaction steps have been monitored by 1H NMR on the support directly.",

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AU - Chen, Hsia Yuan

AU - Kulkarni, Manohar V.

AU - Chen, Chih Hau

AU - Sun, Chung-Ming

PY - 2008/6/30

Y1 - 2008/6/30

N2 - Chemical stability and reactivity of a bifunctional polymer conjugate containing an ortho-amino arylamide linkage have been successfully exploited to achieve a parallel synthesis of methoxycarbonylated head-tail bis-benzimidazoles. Regioselective alkylation of the two nitrogens in the benzimidazolone moiety has been carried out by ipso-fluoro displacement, and N-alkylation to generate two diversities. Cleavage of the polymer support has resulted in two libraries of di- and tri-substituted benzimidazolyl benzimidazolones in high purity and high yield. All reaction steps have been monitored by 1H NMR on the support directly.

AB - Chemical stability and reactivity of a bifunctional polymer conjugate containing an ortho-amino arylamide linkage have been successfully exploited to achieve a parallel synthesis of methoxycarbonylated head-tail bis-benzimidazoles. Regioselective alkylation of the two nitrogens in the benzimidazolone moiety has been carried out by ipso-fluoro displacement, and N-alkylation to generate two diversities. Cleavage of the polymer support has resulted in two libraries of di- and tri-substituted benzimidazolyl benzimidazolones in high purity and high yield. All reaction steps have been monitored by 1H NMR on the support directly.

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DO - 10.1016/j.tet.2008.04.081

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JO - Tetrahedron

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