Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

John M. Gardiner; Jonathan Procter

doi:10.1016/S0040-4039(01)00935-2

Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

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Abstract

N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol for diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. © 2001 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5109-5111
Number of pages	2
Journal	Tetrahedron Letters
Volume	42
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(01)00935-2
Publication status	Published - 23 Jul 2001

Keywords

Alkylation; Dealkylation; Heterocyclization (prepn. of N-alkoxybenzimidazoles with differentiated C2 and O-substituents)

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10.1016/S0040-4039(01)00935-2

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title = "Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents",

abstract = "N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol for diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. {\textcopyright} 2001 Elsevier Science Ltd.",

keywords = "Alkylation; Dealkylation; Heterocyclization (prepn. of N-alkoxybenzimidazoles with differentiated C2 and O-substituents)",

author = "Gardiner, {John M.} and Jonathan Procter",

year = "2001",

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doi = "10.1016/S0040-4039(01)00935-2",

language = "English",

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journal = "Tetrahedron Letters",

issn = "1873-3581",

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TY - JOUR

T1 - Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

AU - Gardiner, John M.

AU - Procter, Jonathan

PY - 2001/7/23

Y1 - 2001/7/23

N2 - N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol for diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. © 2001 Elsevier Science Ltd.

AB - N-Alkoxy-, N-aryloxy- and N-allyloxybenzimidazoles (prepared using tandem N-alkylation, heterocyclisation and O-alkylation with in situ alkylating agent) can be selectively O-deprotected and then independently realkylated to provide a protocol for diversification with differentiated substituents at C2 and on oxygen. In addition, carboxamide functionalised derivatives 8 are amenable to staged interruption of the tandem reaction, allowing sequential additions of two different bases and alkylating agents directly affording 9. This 'start-stop-start' tandem process also facilitates diversification to analogues bearing different C2 and N-alkoxy substituents. © 2001 Elsevier Science Ltd.

KW - Alkylation; Dealkylation; Heterocyclization (prepn. of N-alkoxybenzimidazoles with differentiated C2 and O-substituents)

U2 - 10.1016/S0040-4039(01)00935-2

DO - 10.1016/S0040-4039(01)00935-2

M3 - Article

SN - 1873-3581

VL - 42

SP - 5109

EP - 5111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Synthesis of N-alkoxybenzimidazoles with differentiated C2 and O-substituents

Abstract

Keywords

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