A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines

Prashant Mujumdar; Tanja Grkovic; Mikhail Krasavin

doi:10.1016/j.tetlet.2013.04.036

A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines

Prashant Mujumdar
, Tanja Grkovic
, Mikhail Krasavin

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

14 Citations (Scopus)

Abstract

We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores.

Original language	English
Pages (from-to)	3336-3340
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2013.04.036
Publication status	Published - 26 Jun 2013
Externally published	Yes

Keywords

Bechamp reduction
Benzimidazoles
Imidazo[4,5-b]pyridines
N-(Hetero)aryl 2-imidazolines
Pd-catalyzed arylation
Rearrangement

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10.1016/j.tetlet.2013.04.036

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title = "A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines",

abstract = "We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores.",

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T1 - A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines

AU - Mujumdar, Prashant

AU - Grkovic, Tanja

AU - Krasavin, Mikhail

PY - 2013/6/26

Y1 - 2013/6/26

N2 - We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores.

AB - We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores.

KW - Bechamp reduction

KW - Benzimidazoles

KW - Imidazo[4,5-b]pyridines

KW - N-(Hetero)aryl 2-imidazolines

KW - Pd-catalyzed arylation

KW - Rearrangement

UR - https://www.scopus.com/pages/publications/84878403424

U2 - 10.1016/j.tetlet.2013.04.036

DO - 10.1016/j.tetlet.2013.04.036

M3 - Article

AN - SCOPUS:84878403424

SN - 0040-4039

VL - 54

SP - 3336

EP - 3340

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines

Abstract

Keywords

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