Synthesis of β-D-ribofuranosylbenzazoles using nitrile oxide addition chemistry

Smellie, Iain A.; Paton, R. M.

doi:10.3998/ark.5550190.0013.905

Cited by 5 publications

(1 citation statement)

References 15 publications

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“…This procedure was originally described by Sasaki and co-workers using benzenecarbohydroximoyl chloride, 39 and then extended by Paton and coworkers to carbohydrate-based hydroximoyl chlorides 22 for the synthesis of peracetylated 2-(-D-glucopyranosyl)benzimidazole 23 and 2-(-D-glucopyranosyl)benzimidazole 24 (Scheme 5). 40,41 2-(-D-Xylopyranosyl)-and 2-(-D-galactopyranosyl)-derived benzimidazoles were This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.…”

Section: With (Het)arenecarboxylic Acid Derivativesmentioning

confidence: 99%

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Мамедов¹,

Zhukova²

2021

Synthesis

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Benzimidazole is an important heterocycle that is widely researched and utilized by the pharmaceutical industry and is one of the five most commonly used five-membered aromatic heterocyclic compounds approved by the US Food and Drug Administration. In view of their wide-ranging bioactivities, systems containing benzimidazole as one of the moieties occupy a special place among other benzimidazole derivatives. Since 2010, many improved synthetic strategies have been developed for the construction of hetaryl- and arylbenzimidazole molecular scaffolds under environmentally benign conditions. This review emphasizes the recent trends and modifications frequently used in the synthesis of derivatives of benzimidazole such as the Phillips–Ladenburg and Weidenhagen reactions, as well as entirely new methods of synthesis, involving oxidative cyclization, cross-coupling, ring distortion strategy, and rearrangements carried out under environmentally benign conditions.1 Introduction2 From 1,2-Diaminobenzenes with Various One-Carbon Unit Suppliers2.1 Phillips–Ladenburg Reaction2.1.1 With (Het)arenecarboxylic Acids2.2.2 With (Het)arenecarboxylic Acid Derivatives2.2 Weidenhagen Reaction2.2.1 With (Het)arenecarbaldehydes or (Het)aryl Methyl Ketones2.2.2 With Primary Alcohols2.2.3 With Primary Alkylamines2.2.4 With 2-Methylazaarenes2.2.5 With Other One-Carbon Fragment Suppliers3 From 2-Haloacetanilides and Amines4 From Amidines5 From Tetrahydroquinazolines6 Mamedov Rearrangement7 Conclusions and Outlook

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Section: With (Het)arenecarboxylic Acid Derivativesmentioning

confidence: 99%

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Мамедов¹,

Zhukova²

2021

Synthesis

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Approaches to the synthesis of heterocyclic C-nucleosides

2023

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This review is focused on the synthetic strategies to heterocyclic C-nucleosides and covers the literature from 2011 to 2021. The main attention is paid to the following three approaches: the direct C-C coupling of a carbohydrate moiety with a preformed aglycon unit, the construction of a (pseudo)sugar residue on a pre-formed aglycon, and the construction of an aglycon on a pre-formed (pseudo)sugar. In each Section, the literature data are categorized in terms of the size of aglycon from simple to complex, the advantages and drawbacks of the reviewed approaches are discussed.

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