Parallel Synthesis of Polyethylene Glycol Supported Biaryl Benzimidazoles and Imidazopyridines

Blettner, Carsten G.; König, Wilfried Α.; Rühter, Gerd; Stenzel, Wolfgang; Schotten, Theo

doi:10.1055/s-1999-2598

Cited by 46 publications

(22 citation statements)

References 4 publications

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“…They later used the same strategy to synthesise 1H-benzimidazoles, 1H-imidazo [4,5-b]pyridines 107 and 1H-imidazo [4,5-c]pyridines. 108 Varma 109 investigated the effect of various bases on the PEG-based coupling reaction in the presence of microwave irradiation (Scheme 47) and found KF to be the most convenient protocol. The use of other bases requires water as the co-solvent for their dissolution, which not only reduces the solubility of the aromatic halides but also increases the self-coupling products of the boronic acids.…”

Section: Varma and Naickermentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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Section: Varma and Naickermentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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“…1 antagonists acting as good NMDA (N-methyl-D-aspartate) antagonists [125], and also form versatile intermediates. Phillips Similarly, parallel synthesis of 2,5-biaryl benzimidazoles has been generated on soluble PEG support [123].…”

Section: Strategy IImentioning

confidence: 99%

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Kamal¹,

Reddy²,

Devaiah

et al. 2006

MRMC

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Quinoxaline, quinazoline and benzimidazole based templates have been synthesized on solid-support employing different methodologies. This review enlightens academic and industrial examples of combinatorial synthesis for this type of heterocycles that appeared in the literature in the last decade. Hence, some of the important synthetic strategies for the generation of quinoxaline, quinazoline and benzimidazole based privileged structures, and the important biological activities for these heterocycles have been highlighted. Further, benzothiadiazinone, thioxoquinazolinone, cinnoline and indazole are also examined in this review.

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“…Atmospheric oxygen [65], nitrobenzene [66,67], iodine [68], iron(III) salts [69], and sulfur [70,71] can be used as oxidizing agents at the last stage. Oxidation with atmospheric oxygen was used in the solid-phase synthesis of 7-azabenzimidazoles during the creation of combinatorial libraries [72].…”

mentioning

confidence: 99%

Synthetic approaches to imidazo[4,5-b]pyridine derivatives (review)

Bukhryakov

Kurkin

Yurovskaya

2011

Chem Heterocycl Comp

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Data on methods for the production of derivatives of imidazo [4,5-b]pyridines are reviewed.Keywords: imidazo [4,5-b]pyridines, diaminopyridine derivatives, annelation of pyridine ring, annelation of imidazole fragment, simultaneous formation of two condensed rings. The interest in imidazopyridines arises from their diverse biological activity. Data on the biological activity of imidazole derivatives were reviewed in [1]. They are analgesic [2] and nonsteroidal antiinflammatory agents [2, 3], exhibit antidepressant [4], cardiotonic [5], hypotensive, antiarrhythmic [6], and antisecretory [7] activity. Among compounds of this class antagonists of angiotensin II receptors that exhibit hypotensive activity are known [8,9]. In addition, a number of the imidazo[4,5-b]pyridines possess antiviral [10], antimicrobial [11], and cytotoxic [12] activities. Other aspects of the practical application of derivatives of imidazopyridines are known; for example, they are used in agriculture for the treatment of the shoots of broadleaved plants [13,14] and in the fight against rodents [15].A review of existing published data on methods for the synthesis of imidazo[4,5-b] pyridines derivatives is of undoubted interest in this connection. The information summarized in this review may be useful in the design and development of methods for the synthesis of functional derivatives of imidazopyridines and pyridopyrazines, which are prospective heterocyclic compounds for use in the search for new biologically active substances.The most useful starting compounds for the synthesis of imidazo [4,5-b]pyridines are the readily obtainable derivatives of 2,3-diaminopyridine, which are usually produced in two stages from the commercially available 2-chloro-3-nitropyridine [16] or 2-fluoro-3-nitropyridine [17]. The first stage involves nucleophilic substitution of the halogen in the pyridine ring activated by the nitro group. Reduction of the nitro group leads to the required derivative of 2,3-diaminopyridine, where the reducing agent is hydrogen in the presence of palladium on carbon [18], Raney nickel [19], sodium bisulfite, sodium borohydride, zinc, or iron in the presence of acid [19].

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Parallel Synthesis of Polyethylene Glycol Supported Biaryl Benzimidazoles and Imidazopyridines

Cited by 46 publications

References 4 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Synthetic approaches to imidazo[4,5-b]pyridine derivatives (review)

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