Synthetic Applications of Azolium Ylides to a Traceless Solid-Phase Synthesis of 2-Substituted Azoles

Deng, Yunkun; Hlasta, Dennis J.

doi:10.1021/ol0266727

Cited by 27 publications

(12 citation statements)

References 14 publications

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“…An example of this second approach is the carbamyl chloride linker unit 21 described by Hlasta for the preparation of 2-substituted imidazoles. [30] The linker unit 21 was prepared from N-(methylaminomethyl)polystyrene and phosgene. A one-pot reaction with benzaldehyde and 1-benzylimidazole then gave the resin-bound 2-substituted imidazole 22.…”

Section: Diversity Through a Nucleophilic Componentmentioning

confidence: 99%

Diversity Linker Units for Solid‐Phase Organic Synthesis

Scott

Steel

2006

Eur J Org Chem

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In recent years an ever‐increasing number of traditional solution‐phase reactions have been adapted for solid‐phase organic synthesis (SPOS) because of the ease of application of solid‐phase techniques to combinatorial chemistry and high‐throughput screening. To accommodate the growing number of reactions being attempted on solid supports, new linker units continue to be reported in the literature. Linker units are typically grouped according to the functionality left at the “cleavage site” in the target molecule, and are normally classified as traditional (polar functionality remains following cleavage) or traceless (hydrogen residue left after cleavage) linkers. As the field continues to expand, however, more advanced linker units have been reported, which utilise the cleavage step in SPOS to incorporate additional diversity into target libraries. These linker units have been termed “diversity” or “multifunctional” linker units, and in this microreview we introduce this aspect of the field, giving representative examples indicating key stages of development including the linker units recently designed in our laboratory. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Diversity Through a Nucleophilic Componentmentioning

confidence: 99%

Diversity Linker Units for Solid‐Phase Organic Synthesis

Scott

Steel

2006

Eur J Org Chem

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“…Hlasta and Deng have developed a two-step solid-phase method for the decoration of azoles at C-2 [188]. First, imidazole was loaded onto a polystyrenebound carbamyl chloride via a benzaldehyde bridge (Fig.…”

Section: Microwave-assisted Substitution Of Imidazole C-2 On Solid-phasementioning

confidence: 99%

Solid-Phase Methods for the Microwave-Assisted Synthesis of Heterocycles

Erdélyi

2006

Topics in Heterocyclic Chemistry

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“…They can be deprotonated at their C-atom to form azolium ylides, which can be trapped with benzaldehyde. Intramolecular transacylation involving the polymer-bound carboxyl group ensues to give the a-acyloxy methyl imidazole [487] (Scheme 136). …”

Section: Procedures 80mentioning

confidence: 99%